Co-reporter:Chun-Guang Dai, Ji-Long Wang, Ying-Long Fu, Hong-Ping Zhou, and Qin-Hua Song
Analytical Chemistry October 3, 2017 Volume 89(Issue 19) pp:10511-10511
Publication Date(Web):September 11, 2017
DOI:10.1021/acs.analchem.7b02680
Nitric oxide (NO) is an important signaling molecule involved in many physiological and pathological processes. To understand these NO-mediated processes, it is a key to develop rapid and specific detection methods for NO. In the past 2 decades, numerous excellent fluorescent probes for NO have been designed; however, it still remains limitations such as slow response, low selectivity, and short excitation wavelength (<600 nm). In this Article, a two-photon fluorescent probe, NO-QA5, has been developed with 3-dimethylaminophenyl linking at the 6-position of 5-aminoquinoline as both the active site and prefluorophore for detection of NO. The nonfluorescent NO-QA5 can fast react with NO via a diazonium intermediate to generate two azoic regioisomers, one of which exhibits intramolecular charge transfer (ICT) emission, and two-photon absorption behavior (δΦ = 57 GM), giving a turn-on fluorescence rapid response. The sensing reaction is pH-insensitive in the range of 6–11 and highly selective and well sensitive (LOD = 15 nM), possible undergoing the same intermediate diazonium with the reaction under diazotization condition (NaNO2/HCl). Also, as a nitrite fluorescent probe NO-QA5 exhibits highly sensitive (LOD = 7 nM). Therefore, NO-QA5 can serve as a dual functional fluorescent probe for NO and NO2–. Furthermore, NO-QA5 as a specific imaging agent has been demonstrated by achieving both exogenous and endogenous detections of NO in living cells under both one- and two-photon excitation and high resolution in tissue slices under two-photon excitation.
Co-reporter:Hong Li;Yuncang Li;Huihui Zhang;Guoyong Xu;Yuliang Zhang;Xiaohu Liu;Hongping Zhou;Xingyuan Yang;Xuanjun Zhang;Yupeng Tian
Chemical Communications 2017 vol. 53(Issue 99) pp:13245-13248
Publication Date(Web):2017/12/12
DOI:10.1039/C7CC07288K
The conveniently obtained water-soluble small-molecule L1–5 were selective for RNA with remarkable “off–on” two-photon fluorescence responses in vitro and in vivo, showing that L1–5 can surprisingly stain mitochondria or nucleoli individually with orange fluorescence under different focal lengths. Compounds L6–8 were prepared, for comparison, to further explore the mechanism of the binding of L1–5 with RNA, which revealed that the synergistic effect of the amino group and the pyridinium cation played a significant role in distinct cell imaging.
Co-reporter:Hong Li;Ruilong Zhang;Chunxia Li;Bei Huang;Tingting Yu;Xiaodan Huang;Xuanjun Zhang;Fei Li;Hongping Zhou;Yupeng Tian
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 3) pp:598-604
Publication Date(Web):2017/01/18
DOI:10.1039/C6OB02384C
A triphenylamine–pyridine derivative, viz., a fluorescence probe was designed and synthesized. The probe displayed an “on–off–on” fluorescence switch, upon the sequential addition of Cu2+ and ethylenediaminetetraacetic acid (EDTA). The detection mechanism was confirmed by using UV-vis, fluorescence and 1H NMR titration spectra. Interestingly, the probe can accumulate in mitochondria, and thus detect Cu2+ in real-time there, which indicated that probe L can be used to monitor intracellular mitochondrial Cu2+ levels. Further understanding of the biological functions of Cu2+ in mitochondria has important implications for treating cancer and other diseases.
Co-reporter:Xiaoping Gan;Guangjin Liu;Mingjie Chu;Wengang Xi;Zili Ren;Xiuli Zhang;Yupeng Tian;Hongping Zhou
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 9) pp:2119-2119
Publication Date(Web):2017/03/01
DOI:10.1039/C7OB90023F
Correction for ‘Intermolecular interactions boost aggregation induced emission in carbazole Schiff base derivatives’ by Xiaoping Gan, et al., Org. Biomol. Chem., 2017, 15, 256–264.
Co-reporter:Xiaoping Gan;Guangjin Liu;Mingjie Chu;Wengang Xi;Zili Ren;Xiuli Zhang;Yupeng Tian;Hongping Zhou
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 1) pp:256-264
Publication Date(Web):2016/12/20
DOI:10.1039/C6OB02181F
Six D–π-A model compounds (compounds 1–6) were conveniently synthesized and characterized by 1H NMR, 13C NMR, MS and single crystal X-ray diffraction. One photon absorption and emission properties were studied by using a series of UV-visible and fluorescence spectra and theoretical calculations were applied to investigate the structure–property relationships, which showed that all six compounds possessed an obvious intramolecular charge transfer process which could be attributed to their optical properties. We simultaneously investigated their fluorescence emission performance in water/acetonitrile mixtures and found that they all have outstanding aggregation induced emission properties. Scanning electron microscopy testing illustrated that orderly aggregation was the main reason for their aggregation induced emission properties. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, and bio-imaging studies highlighted the potential application of the six compounds in one-photon fluorescence microscopy imaging domains.
Co-reporter:Dan Liu, Haiyan Wang, Hong Li, Huihui Zhang, Qingsong Liu, Zepeng Wang, Xiaoping Gan, Jieying Wu, Yupeng Tian, Hongping Zhou
Dyes and Pigments 2017 Volume 147(Volume 147) pp:
Publication Date(Web):1 December 2017
DOI:10.1016/j.dyepig.2017.08.033
•Six benzoxazole-based compounds 1–6 with different anions were obtained by methylation and anion exchange reaction.•Compounds 1–6 showed good two-photon absorption properties in water solvent.•Compounds 1–6 were applied in live cell imaging, which highlighted their practical performance.Six new benzoxazole-based compounds 1–6 of the donor-bridge-accepter (D-π-A) type with different anions were obtained by methylation and anion exchange reaction. The single crystals of 1, 3 and 6 were obtained by slow evaporation of acetonitrile and determined by X-ray crystallography. Ellipsoidal structures of the three compounds showed that the cationic parts all maintained good planarity, which was beneficial for two-photon absorption (2PA) properties and accorded with the results of two-photon excited fluorescence tests. Biological imaging experiments showed water-soluble six compounds had excellent penetrability in living cells and could located in cytoplasm in one- and two-photon cell imaging. Biological imaging result of compound 6 was more excellent than other compounds, which indicated synergy of anions and cations played a very important role in cell imaging.Excellent solubility in water media of six new benzoxazole-based compounds 1–6 with different anions could apply in biological imaging. Ellipsoidal structures of 1, 3 and 6 showed that the cationic parts all maintained good planarity, which was beneficial for two-photon absorption (2PA) properties. The two-photon cell imaging results showed that 1–6 had excellent penetrability in living cells and could located in cytoplasm.Download high-res image (298KB)Download full-size image
Co-reporter:Shun Yao, Xin Zhang, Haiyan Wang, Hui Wang, Xiaoping Gan, Zhichao Wu, Yupeng Tian, Zhongwen Pan, Hongping Zhou
Dyes and Pigments 2017 Volume 145(Volume 145) pp:
Publication Date(Web):1 October 2017
DOI:10.1016/j.dyepig.2017.05.059
•The structures of T1 and T3 were determined by single crystal X-ray diffraction analysis.•The twisted molecular conformation facilitated aggregation-induced emission enhancement.•T2 and T3 were applied in live cell imaging, which highlighted their practical performance.Three novel 2-(4-methoxyphenyl)-1, 3, 4-thiadiazole based Schiff base derivatives (T1-T3) had been synthesized and characterized by 1H NMR, 13C NMR, MS and IR. The spectroscopic properties of T1-T3 were investigated by UV–vis absorption and fluorescence emission spectroscopy, which were coincident with theoretical calculations that three compounds possessed obvious intramolecular charge transfer (ICT) process. Their fluorescence emission performance in solution and aggregation state showed that three compounds all owned obvious aggregation-induced emission enhancement (AIEE) properties. To further understand AIEE nature, dynamic light scattering (DLS) and scanning electron microscopy (SEM) were comparatively investigated, which demonstrated that the small and uniform particles contributed to improve fluorescence emissions. Crystal structures of T1 and T3 showed that the twisted molecular conformation played an important role in AIEE. What's more, T2 and T3 had good biocompatibility, which were successfully applied in live-cell imaging.The structure-property relationship of three new AIEE compounds were discussed, which showed the twisted molecular conformation avoiding π … π stacking facilitated aggregation-induced emission enhancement.Download high-res image (212KB)Download full-size image
Co-reporter:Xiaoping Gan, Xinping Ge, Chengkai Zhai, Jun Zheng, Xuguang Tang, Yanchao Yang, Yupeng Tian, Xuanjun Zhang, Hongping Zhou
Dyes and Pigments 2017 Volume 138(Volume 138) pp:
Publication Date(Web):1 March 2017
DOI:10.1016/j.dyepig.2016.11.019
•Four asymmetric bis-branched triphenylamine derivatives were easily synthesized.•The branched triphenylmines possessed large two-photon cross-sections and low biotoxicity.•The intramolecular charge transfer from one branch to another plays an important role.•The branched triphenylamines were successfully applied in one- and two-photon fluorescence bio-imaging.Four asymmetric bis-branched triphenylamine-cored compounds with different electron-withdrawing groups have been synthesized and their optical properties have been systematically investigated. The two-photon absorption cross-section (σ2PA) values were measured by two-photon excited fluorescence which revealed that the four compounds possessed large σ2PA values from 2011 to 4173 GM in the near-infrared region. Theoretical calculations revealed that the compounds were all provided with interesting intramolecular charge transfer generated from one branch to the other which contributed to the large σ2PA values. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, both one- and two-photon fluorescence microscopy studies showed the potential application of the four new compounds in cell imaging due to the large σ2PA and appropriate biocompatibility.Download high-res image (250KB)Download full-size image
Co-reporter:Xin Zhang, Xiaodan Huang, Xiaoping Gan, Zhichao Wu, Jianhua Yu, Hongping Zhou, Yupeng Tian, Jieying Wu
Sensors and Actuators B: Chemical 2017 Volume 243() pp:421-428
Publication Date(Web):May 2017
DOI:10.1016/j.snb.2016.11.161
•L1 showed a novel MC property based on crystalline–amorphous phase transformation.•The structure-relationship between AIE and Mechanofluorochromism were investigated.•Two colorimetric and fluorometric probes can detect Cu (II).•The limit of detection of this probe was calculated as low as 2.32 × 10−6 M and 9.268 × 10−7 M for Cu2+, respectively.Herein, we designed and synthesized two novel probes 4-(2-Hydroxy-phenylimino)-4′-(1, 4, 7, 10-tetraoxa-13-azacyclopentadecyl)-1- cyanostilbene (L1) and 4-(2-Hydroxy-phenylimino)-4′-(1, 4, 7, 10-tetraoxa-13-aza cyclopentadecyl) stilbene (L2) with aggregation induced emission behavior. L1 can directly recognize Cu2+ with high selectivity and specificity in water, L2 can distinguish Cu2+ with naked-eye in acetonitrile. Moreover, L1 and L2 with aggregation-induced emission could be applied to bio-imaging, and L1 showed a switchable color change feature based on mechanical grinding. The mechanism of the mechanochromic behavior was fully investigated by powder X-ray diffraction, single-crystal structures and differential scanning calorimetry measurements.Two novel probes based on aza-crown ether Schiff base (L1, L2) designed to distinguish Cu2+. Moreover, L1 and L2 with aggregation-induced emission could be applied to bio-imaging, and L1 showed a switchable color change feature based on mechanical grinding.
Co-reporter:Xiaoping Gan, Wei Li, Chunxia Li, Zhichao Wu, Dan Liu, Bei Huang, Hongping Zhou, Yupeng Tian
Sensors and Actuators B: Chemical 2017 Volume 239() pp:642-651
Publication Date(Web):February 2017
DOI:10.1016/j.snb.2016.08.042
•Two novel similar structural Schiff base “off-on” fluorescent probes for detection of Al3+ were reported.•The detection limit of the two probes were calculated to be 1.22 × 10−7 and 2.99 × 10−7 M for Al3+, respectively.•The “off-on” fluorescent probes were both applied in live cell imaging successfully.Two similar structural triphenylamine-based Schiff bases “off-on” fluorescent probes for detecting Al3+ through naked eye manner were prepared by changing their bridging groups, one via styrene (LW1), the other via phenethyl (LW2). This modification affected the performance remarkably in terms of selectivity, sensitivity and efficiency as well as recognition mechanism. The experimental results showed probe LW1 can selectively detect trivalent ion especially for Al3+ by hydrolysis-chelation-enhanced fluorescence with a detection limit of 1.22 × 10−7 M. However, probe LW2 can only highly selectively detect for Al3+ by the direct chelation-enhanced fluorescence with a detection limit of 2.99 × 10−7 M. Furthermore, benefiting from their good water solubility and biocompatibility, cell imaging and real-time monitoring of Al3+ in living HepG2 cells were successfully achieved.Two novel triphenylamine-based Schiff base derivatives LW1 and LW2 were synthesized by changing bridging groups and utilized as Al3+ fluorescent turn-on probes based on distinct mechanisms, respectively. LW1 exhibited selective fluorometric sensing for Al3+ ions because of metal-promoted hydrolysis and chelation. LW2 displayed specific recognition ability toward Al3+ ions by direct chelation-enhanced fluorescence (CHEF).
Co-reporter:Xinping Ge, Xiaoping Gan, Shun Yao, Kang Wang, Weiju Zhu, Jianhua Yu, Jieying Wu, Yupeng Tian and Hongping Zhou
Journal of Materials Chemistry A 2016 vol. 4(Issue 16) pp:2785-2793
Publication Date(Web):22 Mar 2016
DOI:10.1039/C6TB00201C
A new series of benzoxazole-based two-photon absorption (2PA) chromophores (T1–5) were synthesized and fully characterized. Among them, T1–3 are linear donor (D)–π–acceptor (A) type fluorophores with various electron-donating groups, while T4 and T5 are multi-branched compounds stemming from T3. Their photophysical properties have been systematically investigated, and the two-photon absorption properties indicate that the highest 2PA cross-section (σ2PA) is 2702 GM for T5 (in DMF). Structure–property relationships of the chromophores are comprehensively discussed based on their optical properties, crystal structures and density functional theory (DFT) calculations. In addition, a two-photon fluorescence cell imaging experiment demonstrates the potential bio-application of T1–5 with good photostability and low cytotoxicity.
Co-reporter:Na Zhang, Xiaohe Tian, Jun Zheng, Xiuzhen Zhang, Weiju Zhu, Yupeng Tian, Qiyong Zhu, Hongping Zhou
Dyes and Pigments 2016 Volume 124() pp:174-179
Publication Date(Web):January 2016
DOI:10.1016/j.dyepig.2015.09.019
•A novel fluorescent benzimidazole derived probe was designed and synthesized.•The probe showed selective and sensitive recognition toward Zn2+.•The detection limit of the probe was 5.1 × 10−8 M for Zn2+.•The probe can be used in live cell imaging.A novel fluorescent probe for Zn2+ has been designed and synthesized based on a dipicolylamine group connected by a benzimidazole amide backbone. A comprehensive analysis of the recognition ability of the probe towards metal ions was conducted by ultraviolet absorption and fluorescence emission spectroscopy. Results demonstrated that the probe showed selective and sensitive fluorescence turn-on signaling behavior toward Zn2+ in HEPES buffered (pH = 7.4) aqueous solution. The detection limit of this probe was calculated to be 5.10 × 10−8 M for Zn2+. Fluorescent imaging inside HepG2 cells indicated potential application of the probe for detecting Zn2+ ions in living cell imaging.
Co-reporter:Wei Li, Xiaoping Gan, Dan Liu, Xiaohe Tian, Jianhua Yu, Yupeng Tian, Jieying Wu and Hongping Zhou
RSC Advances 2016 vol. 6(Issue 50) pp:44599-44605
Publication Date(Web):28 Apr 2016
DOI:10.1039/C6RA05699G
An easily available triphenylamine–isophorone-based Schiff base was synthesized and its specifically triple-addressable molecular photo-switching behaviour via copper ion recognition, trans–cis isomerization and ring closure were investigated in detail. Firstly, compound Lo was able to real-time monitor Cu2+ in an acetonitrile solution via displaying the “turn-on” emission in the near infrared region with high selectivity, and sensitivity. Furthermore, two independently photochromic phenomena based on the distinct mechanisms were found surprisingly, one through the ring closure of the thiosemicarbazide moiety based on a Michael addition reaction in tetrahydrofuran solution and another through the trans–cis isomerization of aldimine (–CN–) in the solid state under the stimuli of UV/visible light. Finally, fluorescence imaging experiments in living cells demonstrated the potential practical applications in biological systems.
Co-reporter:Xin Zhang, Xiaoping Gan, Shun Yao, Weiju Zhu, Jianhua Yu, Zhichao Wu, Hongping Zhou, Yupeng Tian and Jieying Wu
RSC Advances 2016 vol. 6(Issue 65) pp:60022-60028
Publication Date(Web):13 Jun 2016
DOI:10.1039/C6RA09701D
Three branched molecules (T1–T3) were synthesized through simple step to realize or enhance two-photon absorption (2PA) in aggregates. Spectra data show that one- and two-branched molecules (T1 and T2) possessed remarkable AIE properties, which came from the formation of J-aggregation because of their partial planarization in an aggregated state. SEM and DLS illustrate that the ordered aggregation and the small particle size had an important influence on fluorescence emission. Open aperture Z-scan experiments show that T1 and T2 possessed excellent 2PA properties in the aggregated state. The largest 2PA cross section was 8314 GM for T2 in aggregates, which was about 13-fold higher than that in pure solution. All the results demonstrate that the compounds could obtain outstanding 2PA performance by rationally adjusting their structure or changing state, which could provide a reference for preparing strong 2PA compounds.
Co-reporter:Tingting Yu, Ping Sun, Yijie Hu, Yinggang Ji, Hongping Zhou, Baowei Zhang, Yupeng Tian, Jieying Wu
Biosensors and Bioelectronics 2016 Volume 86() pp:677-682
Publication Date(Web):15 December 2016
DOI:10.1016/j.bios.2016.07.057
•A new fluorescence probe with high selectivity for magnesium and no interference from calcium is developed.•The probe can be utilized to detect magnesium ion in lysosome of living cells.•The probe can be successfully used as a magnesium ion developer in living plant tissues.A simple-molecule fluorescence probe L has been designed, synthesized and characterized, which shows high selectivity and sensitivity for the main group magnesium ion through fluorescence “turn-on” response in ethanol solution, and no interference from calcium ion in particular. Detection limit of probe L is 1.47×10−6 M and the rapid response could reach about 15–20 s. The recognition mechanism has been established by fluorescence spectra, 1H NMR study. Moreover, probe L presents a great photostability, low toxicity and cellular permeability, then we have carried out fluorescent bio-imaging of the probe L for magnesium ions in HeLa cells, which showed that probe L could be utilized to detect the intracellular magnesium ion. Furthermore, it is successfully used as a magnesium ion developer in plant tissues, which shows that it not only can be well tracking the transport of magnesium ion but also make a corresponding fluorescence response to different concentrations magnesium ion. These results would make this probe a great potential application for detecting Mg2+ in biological system.
Co-reporter:Xiaoping Gan, Ping Sun, Hong Li, Xiaohe Tian, Baowei Zhang, Jieying Wu, Yupeng Tian, Hongping Zhou
Biosensors and Bioelectronics 2016 Volume 86() pp:393-397
Publication Date(Web):15 December 2016
DOI:10.1016/j.bios.2016.06.087
•The synthesis of the probe was very convenient and response time was short.•The limit of detection of probe was calculated as low as 5.8 nM for Zn2+.•The probe could be unitized to detect zinc ions visually in the intracellular endogenous and Arabidopsis tissues.In this paper, we reported a conveniently prepared fluorescent probe for zinc ions detection, which constructed by the condensation reaction between p-(benzothiazolyl)aniline with 4, 4- diethylaminesalicylaldehyde. The sensing ability of the probe toward zinc ions in vitro was tested by a series of UV-Vis and fluorescence spectroscopy studies, which showed that the probe possessed high sensitivity with a detection limit of 5.8 nM and a rapid response time of 10 s. We also carried out fluorescent bio-imaging of the probe for zinc ions in human liver hepatocellular carcinoma cells (HepG2), which showed that the probe could be utilized to detect the intracellular endogenous zinc ions visually without introducing external zinc sources. Meanwhile, co-staining experiment with organelle selective trackers was performed to illustrate that the probe could locate at endoplasmic reticulum. Finally, we successfully used it as a zinc ion developer in plant tissue, which clearly demonstrated the distribution of zinc ions in the growth stage of plant tissue.
Co-reporter:Wei Li, Xiaohe Tian, Bei Huang, Huijuan Li, Xiaoyu Zhao, Shan Gao, Jun Zheng, Xiuzhen Zhang, Hongping Zhou, Yupeng Tian, Jieying Wu
Biosensors and Bioelectronics 2016 Volume 77() pp:530-536
Publication Date(Web):15 March 2016
DOI:10.1016/j.bios.2015.09.059
•Distinctive recognition mechanisms of L1/L2 toward Al3+/Zn2+ have been established.•The limit of detection of probe L2 was calculated as low as 38.1 nM for Zn2+.•L2 was employed to detect endogenous zinc ion in live tissues at intracellular level.Two novel similar structural triphenylamine-based Schiff base fluorescent probes (L1/L2) were designed, prepared and characterized. Distinctive recognition mechanisms of L1 and L2 toward Al3+ and Zn2+ have been established by UV/vis, fluorescence spectra, mass spectra and 1H NMR studies, respectively. To further explore their utility in biological system, L2 was selected as a probe for live cell endogenous Zn2+ indicator and showed superb sensitivity on Zn2+ intracellular distribution. Furthermore, L2 was employed to selectively detect Zn2+ in live tissues at both extracellular and intracellular level, qualitatively indicated varies zinc concentration as a function of different organs.
Co-reporter:Tingting Yu, Xiaohe Tian, Hong Li, Wei Li, Weiju Zhu, Hongping Zhou, Yupeng Tian, Jieying Wu
Biosensors and Bioelectronics 2016 Volume 82() pp:93-98
Publication Date(Web):15 August 2016
DOI:10.1016/j.bios.2016.03.036
•To date, only a few small-molecule fluorescent probes for Ni2+ have been reported, especially probe L with a simple structure which can be obtained via a one-step reaction.•Probe L thoroughly shows a high selectivity and rapid-response to Ni2+.•Probe L can realize a rapidly reversible on-off-on fluorescence changes and quick detection of Ni2+ in the mitochondria.A simple molecular fluorescent probe L has been designed, synthesized and characterized. The probe upon interaction with different metals ions show high selectivity and sensitivity for Ni2+ through fluorescence “turn-off” response in acetonitrile, and the fluorescence could be recovered when chelating agent TPEN is added in this system, viz an “on-off-on” process. Its recognition mechanism has been established by fluorescence spectra, 1H NMR study. Moreover, to further explore its utility in biological system, L is selected as a probe for Ni2+ indicator in live cells and shows sensitivity on Ni2+ intracellular distribution. Fluorescence co-localization studies demonstrate that L is a specific mitochondria-targeted fluorescent probe with excellent cell membrane permeability. Furthermore, a rapidly reversible fluorescence imaging of probe L detecting Ni2+ in the mitochondria is successfully achieved. These facts would make this probe a great potential for detecting Ni2+ in biology.
Co-reporter:Mingdi Yang, Yan Zhang, Weiju Zhu, Huizhen Wang, Jing Huang, Longhuai Cheng, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2015 vol. 3(Issue 9) pp:1994-2002
Publication Date(Web):24 Dec 2014
DOI:10.1039/C4TC02616K
Three new anthryl Schiff base derivatives containing a similar molecular structure were synthesized through a simple method and their fluorescent properties were investigated in detail. Among these, compound 1 displayed an aggregation-induced emission (AIE) feature, 2 exhibited an aggregation-induced emission enhancement (AIEE) property, while 3 showed aggregation-caused quenching (ACQ) behavior. Single-crystal structure and theoretical calculation analysis show that the larger conjugation and the existence of multiple intra- and intermolecular interactions restricts the intramolecular vibration and rotation, which benefit the emission in the condensed state, while the tight dimer structure and intramolecular torsional motion induce fluorescence quenching. Moreover, compound 2 can be utilized as fluorescence on–off type sensor for Cu2+ in methanol–H2O (4/1, v/v, pH 7.2) HEPES buffer solution, as well as fluorescence off–on type sensor for Zn2+ in pure methanol solution. The 2:1 ligand-to-metal coordination pattern of the 2-Cu2+ and 2-Zn2+ were calculated through a Job's plot, and were further confirmed by X-ray crystal structures of complexes 2-CuBr2 and 2-ZnCl2. In addition, 2 also exhibits a piezofluorochromic characteristic.
Co-reporter:Feng Jin, Wenchao Shu, Xianpeng Yu, Yue Zhang, Lin Sun, Yong Liu, Dongliang Tao, Hongping Zhou, Yupeng Tian
Dyes and Pigments 2015 Volume 121() pp:379-384
Publication Date(Web):October 2015
DOI:10.1016/j.dyepig.2015.05.039
•Two new luminescent zinc dyes were prepared.•The dyes exhibit two-photon excited fluorescence with two-photon absorption cross-section values up to 682 GM.•The structure-property relationships were detailed through X-ray crystallography.•Results of living cell imaging experiments show the value of the dyes in fluorescence microscopy bioimaging applications.Two new luminescent zinc complexes based on a donor–π–bridge- acceptor organic ligand bearing a diphenylamine donor group and 2,2′-bipyridine acceptor group were prepared and characterized. The structures of the dyes were solved by single crystal X-ray diffraction analysis. Research has shown that the dyes exhibit superior two-photon excited fluorescence with the large two-photon absorption cross-section values of over 630 GM. The structure-property relationships were detailed through X-ray crystallography. Results of living cell imaging experiments show the potential of these dyes in fluorescence microscopy bioimaging.
Co-reporter:Wengang Xi, Yubin Zhang, Boyu Chen, Xiaoping Gan, Min Fang, Jun Zheng, Jieying Wu, Yupeng Tian, Fuying Hao, Hongping Zhou
Dyes and Pigments 2015 Volume 122() pp:31-39
Publication Date(Web):November 2015
DOI:10.1016/j.dyepig.2015.06.008
•A novel stilbene-based organic dye was developed.•The dye display trans-cis isomer.•Each isomer has two conformation polymorphs.•AIE behavior of the trans isomer is unusual.Cis-trans isomer and polymorphism of 9-(4-(4-nitrostyryl)phenyl)-9H-carbzole (Dye 1) were obtained unexpectedly. Each isomer has two polymorphs, which was characterized by X-ray single crystal diffraction. Polymorphs T1 and T2 are trans-configuration and both crystallize in monoclinic space group P21/c. Polymorphs C1 and C2 are cis-configuration and crystallize in triclinic space group P-1 and monoclinic space group P21/c, respectively. Trans-isomer shows better stability and higher density than that of cis-isomer, but cis-isomer displays better solubility than that of trans-isomer. The molecular structures and packing arrangements of the four kinds of crystals show different features. The twisted conformation of cis-isomer effectively avoids π-π interactions and close packing. Both the trans and cis isomers show remarkable aggregation-induced emission effect in the acetonitrile/water mixture. In addition, fluorescence cell imaging experiment proves the potential application of the two isomers of dye 1.
Co-reporter:Lianke Wang, Hongping Zhou, Jieying Wu and Yupeng Tian
Dalton Transactions 2015 vol. 44(Issue 21) pp:9921-9926
Publication Date(Web):17 Apr 2015
DOI:10.1039/C5DT01090J
Copper complexes have been frequently involved in many Cu-mediated carbon–hydrogen halogenation reactions. We fortunately obtained three different valence benzoxazolyl–copper complexes, along with aryl carbon–hydrogen bromination, in the self-assembly reaction of ligands with CuBr2. The complexes have been successfully characterized by X-ray single crystal diffraction analyses. The results indicate that 1 consists of di-brominated p-benzoxazolylphenylamine (L) and an unusual high valence copper(III) complex with tetrahedral geometry, 2 is the first polymeric catenulate di-brominated benzoxazolyl-copper(I) complex and 3 is the mono-brominated benzoxazolyl–copper(II) complex. We speculate proposed mechanisms for the formation of these complexes and the bromination of aryl carbon–hydrogen based on these crystal structures.
Co-reporter:Xiaoping Gan, Yang Wang, Xinping Ge, Wei Li, Xiuzhen Zhang, Weiju Zhu, Hongping Zhou, Jieying Wu, Yupeng Tian
Dyes and Pigments 2015 120() pp: 65-73
Publication Date(Web):
DOI:10.1016/j.dyepig.2015.04.007
Co-reporter:Xinping Ge, Jingjing Pi, Weiju Zhu, Xiaoping Gan, Jun Zheng, Xuguang Tang, Yanchao Yang, Hongping Zhou, Jieying Wu, Yupeng Tian
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 151() pp:390-396
Publication Date(Web):5 December 2015
DOI:10.1016/j.saa.2015.06.099
•Two novel TPA-based probes (L1, L2) were synthesized and fully characterized.•Probe L1 exhibited high sensitivity and selectivity for Cu2+.•Probe L2 could respond to Cu2+ and Hg2+ in a short time.•After mixing with Cu2+, L1 and L2 showed great potential application in bioimaging.Two new triphenylamine-cored probes (L1, L2) with different receptor units have been synthesized and fully characterized by IR, NMR and MS spectra. Their photophysical properties have been investigated in detail. The recognition abilities of two probes were evaluated by a series of metal ions, which showed that L1 could recognize Cu2+ over other metal ions. L2 could respond to Cu2+, Hg2+ in a short time, which interferes with a little each other. The Job’s plot and 1H NMR titration of L1 with Cu2+ and L2 with Cu2+ (Hg2+) in CD3CN verified the coordination mode of complexes L1-Cu2+, L2-Cu2+ and L2-Hg2+, respectively. The limit of detection of L2 for Cu2+ was lower than that of L1 towards Cu2+. The results demonstrated that the receptor units in the probes had remarkable effect on recognizing metal ions. Meanwhile, L1 and L2 showed potential application in bio-imaging after mixing with Cu2+.The recognition abilities of two new triphenylamine(TPA)-cored probes (L1, L2) were evaluated by a series of metal ions, which showed that L1 could recognize Cu2+ over other metal ions. L2 could respond to Cu2+, Hg2+ in a short time, but there was a slight interference between each other. Meanwhile, L1 and L2 (or their copper complexes) showed potential application in bioimaging.
Co-reporter:Gang Liu, Mingdi Yang, Lianke Wang, Jun Zheng, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2014 vol. 2(Issue 15) pp:2684-2691
Publication Date(Web):28 Jan 2014
DOI:10.1039/C3TC32591A
Three new Schiff base derivatives possessing vagarious blue aggregation-induced emission (AIE) characteristics in tetrahydrofuran (THF)–water were synthesized. Their photophysical properties in solution, aqueous suspension, film and crystalline states, along with their relationships, were comparatively investigated. The crystallographic data for dye 1 and dye 3 indicated that the existence of multiple intermolecular hydrogen bonding interactions restricted intramolecular vibration and rotation. Moreover, the sizes and growth processes of particles with different water fractions were studied using a scanning electron microscope (SEM) and dynamic light scattering (DLS). The results showed that the small homogeneous particles, assembled in an ordered fashion with appropriate water contents, exhibited distinct AIE behavior. Moreover, in a THF–H2O (4:1, v/v) solution of HEPES (20 mM) buffer, dye 2 showed fluorescence turn-on sensing towards Cr3+ and Al3+via chelation enhanced fluorescence (CHEF). The 2:1 stoichiometries of the sensor complexes (dye 2–Cr3+ and dye 2–Al3+) were calculated from Job plots based on fluorescence titrations.
Co-reporter:Yuanle Cao, Mingdi Yang, Yang Wang, HongPing Zhou, Jun Zheng, Xiuzhen Zhang, Jieying Wu, Yupeng Tian and Zongquan Wu
Journal of Materials Chemistry A 2014 vol. 2(Issue 19) pp:3686-3694
Publication Date(Web):12 Feb 2014
DOI:10.1039/C3TC32551B
A new Schiff-base family containing [4-(1H-benzimidazole-2-yl)-phenyl]-bis-(4-ethoxy-phenyl)-amine has been synthesized through a condensation reaction. All the derivatives possess properties of aggregation-induced and crystallization-enhanced emission (AIE and CEE), which show time-dependent characteristics at a concentration of 10 μM and are studied in detail by scanning electron microscope (SEM) and transmission electron microscope (TEM). Different aggregation forms and the growth of crystals of the compounds, could be responsible for the notably different degrees of fluorescence enhancement.
Co-reporter:Lianke Wang, Yanfang Shen, Mingdi Yang, Xiuzhen Zhang, Weinan Xu, Qiuju Zhu, Jieying Wu, Yupeng Tian and Hongping Zhou
Chemical Communications 2014 vol. 50(Issue 63) pp:8723-8726
Publication Date(Web):19 May 2014
DOI:10.1039/C4CC02564D
Fibrous nanoaggregates of a new benzoxazole-based derivative have been reported. This derivative exhibits not only H-aggregates but also strong yellow fluorescence, which is different from the traditional understanding of H-aggregates.
Co-reporter:Wei Li, Mingdi Yang, Linpan Wang, Weiju Zhu, Lina Ye, Jieying Wu, Yupeng Tian, Hongping Zhou
Dyes and Pigments 2014 Volume 107() pp:133-139
Publication Date(Web):August 2014
DOI:10.1016/j.dyepig.2014.03.034
•We have synthesized two D–π–D dyes with two-photon absorption.•Aza-crown ether was electron donor and stilbene was the conjugated chain.•Linear and nonlinear optical properties of dyes 1 and 2 were investigated.•The results revealed that the dyes 1 and 2 have moderate δ2PA.•SPFM imaging of dye 1 in HepG2 cells was demonstrated.Two novel aza-crown ether derivatives based on stilbene were synthesized and characterized. Their linear photophysical properties were systematically investigated in various solvents. The nonlinear photophysical properties were investigated by two-photon induced fluorescence method. The two-photon absorption cross sections values measured by two-photon excited fluorescence were determined to be 328.2 GM and 246.55 GM for the dyes derived from monoaza 15-crown-5 and 18-crown-6, respectively, which accorded with dipole moment changes under photoexcitation. In addition, a single-photon fluorescence cell imaging experiment proved that dye derived from monoaza 15-crown-5 was suitable for biomedical imaging.
Co-reporter:Feng Jin, Dong-Ling Xu, Hui-Zhi Zhu, Yan Yan, Jun Zheng, Jun Zhang, Hong-Ping Zhou, Jie-Ying Wu, Yu-Peng Tian
Dyes and Pigments 2014 Volume 109() pp:42-53
Publication Date(Web):October 2014
DOI:10.1016/j.dyepig.2014.04.032
•Six new dyes with various electron donors were synthesized in high yield through simple reactions.•The optical properties of the dyes were successfully tuned by the different electron donors.•All dyes in solution show strong one-photon excited fluorescence and high quantum yield.•Dyes 5 and 6 exhibit strong TPEF with large TPA cross-section.•OPFM and TPFM imaging of them in HepG2 cell line was demonstrated.Six new fluorescent donor-π bridge-acceptor (D-π-A) structural molecules with various electron donors were synthesized and fully characterized. Influence of electron-donating strength on optical properties was investigated by the systematic alteration of the electron donors. The optical properties of the dyes were successfully tuned by choosing different electron donors. All the dyes in solution show strong one-photon excited fluorescence (OPEF) and high quantum yield. With increasing electron-donating strength of donors, dye 5 with diphenylamine and dye 6 with (4,4′-diethoxyphenyl)amino substituents, exhibit strong two-photon excited fluorescence (TPEF), and the large two-photon absorption (TPA) cross-section values are 1378 GM for 5 and 1654 GM for 6. The structure–property relationships were detailed through quantum chemical calculations and X-ray crystallography. The results of living cell imaging experiments show the values of them in one- or two-photon fluorescence microscopy bioimaging applications.One- and two-photon fluorescence of six dyes, being promising in bioimaging applications, were successfully tuned through varying electron donors.
Co-reporter:Yuanle Cao, Wengang Xi, Lianke Wang, Huizhen Wang, Lin Kong, Hongping Zhou, Jieying Wu and Yupeng Tian
RSC Advances 2014 vol. 4(Issue 47) pp:24649-24652
Publication Date(Web):16 May 2014
DOI:10.1039/C4RA03042G
Simple modification of triphenylamine generates four luminophores with aggregation-induced emission characteristics. Three of them can be smartly switched in fluorescence emissions by various external stimuli such as grinding, annealing and solvent-fuming, which may be attributed to the transformation from the crystalline state to the amorphous state and vice versa.
Co-reporter:Dongling Xu, Zhipeng Yu, Mingdi Yang, Zheng Zheng, Li Zhu, Xiuzhen Zhang, Lina Ye, Jieying Wu, Yupeng Tian, Hongping Zhou
Dyes and Pigments 2014 100() pp: 142-149
Publication Date(Web):
DOI:10.1016/j.dyepig.2013.09.014
Co-reporter:Lianke Wang ; Yanfang Shen ; Qiuju Zhu ; Weinan Xu ; Mingdi Yang ; Hongping Zhou ; Jieying Wu ;Yupeng Tian
The Journal of Physical Chemistry C 2014 Volume 118(Issue 16) pp:8531-8540
Publication Date(Web):April 1, 2014
DOI:10.1021/jp412279m
The dicyanoisophorone derivatives show obvious AIE behaviors in our previous work. To study the bioimaging application of these chromophores with AIE/AIEE properties, the ester groups substituted for one cyan to form a new family based on isophorone (2a–2e). 2a–2d exhibit obvious AIE/AIEE phenomena, while 2e shows fluorescence quenching in the aggregate state. The morphology and size of aggregates with different water contents were investigated using SEM and DLS, indicating that a large number of smaller globular or quadrate nanoparticles with average diameters in the range 78.79–392.7 nm in mixed solutions are related to these AIE/AIEE or ACQ behaviors. We also made comparative analyses of their optical properties in different states. The crystal data of 2a–2d reveal that the multiple intra- and intermolecular interactions leads to the molecular conformation being more stable, increases the planarity of compounds, restricts the intramolecular motions, and promotes the formation of J-type aggregate, enabling chromophores 2a–2d to emit intensely in the solid state. In addition, the frontier molecular orbital energy and band gap calculated by density functional theory are quite consistent with the experimental results. Finally, these AIE/AIEE-active compounds could be used in bioimaging applications, which immensely provide a new strategy to the application of some AIE/AIEE systems.
Co-reporter:Lian-Ke Wang, Yan-Fang Shen, Hui-Juan Li, Xiao-Yu Zhao, Zheng Zheng, Hong-Ping Zhou, Jie-Ying Wu, Yu-Peng Tian
Journal of Molecular Structure 2014 1068() pp: 182-188
Publication Date(Web):25 June 2014
DOI:10.1016/j.molstruc.2014.04.013
•Novel d10 complexes 1–6 based on multidentate dicyanoisophorone-triazole were obtained.•Zn and Hg atoms are four-coordinated in 1–5. Cd atoms are bridged by μ1,3-SCN in polymer 6.•Rich electronic groups play essential roles in high-dimensional architectures.•1–6 exhibit excellent luminescence and stability.The ligand [(E)-2-(3-(4-(1H-1,2,4-triazole-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile] (L) reacts with Zn(II), Cd(II) and Hg(II) salts, six new complexes, namely HgL2Cl2 (1) HgL2Br2 (2) HgL2I2 (3) ZnL2I2 (4) ZnL2(SCN)2 (5) and [CdL2(μ1,3-SCN)2]n (6) are presented along with an analysis of their structural features. The mercury(II) and zinc(II) ions in 1–5 are four-coordinated by two L and two haloid or thiocyanate ions to form a distorted tetrahedral geometry. In polymer 6, the adjacent Cd(II) ions show an octahedral coordination geometry, which is bridged by two μ1,3-SCN ions to form an infinite chain with two remaining positions of six-coordinated Cd(II) ion being occupied by two L. These structures are built up through the combination of coordination bonds, hydrogen bonding, and π⋯π stacking interactions to generate new supramolecular architectures. Luminescent properties and thermal stabilities of complex 1–6 are studied in the solid state.
Co-reporter:Gang Liu, Jianqing Wang, Mingdi Yang, Xiuzhen Zhang, Lina Ye, Fuying Hao, Hongping Zhou, Xingyou Tian, Jieying Wu, Yupeng Tian
Sensors and Actuators B: Chemical 2014 192() pp: 586-593
Publication Date(Web):
DOI:10.1016/j.snb.2013.10.136
Co-reporter:N. Zhang;L. P. Wang;D. L. Xu;J. H. Yu
Russian Journal of Coordination Chemistry 2014 Volume 40( Issue 10) pp:711-717
Publication Date(Web):2014 October
DOI:10.1134/S1070328414100121
Self-assembly of a multidentate ligand containing pyridyl groups, namely, 6-phenyl-4-(4′-[2-(2-naphthalene)ethenyl]phenyl)-2,2′-bipyridine (L) with corresponding zinc(II) salts, affords a series of coordination complexes, ZnLI2 (I), [ZnLCl2]2 · 2CH2Cl2 (II), ZnLBr2 (III). Complexes I and II were characterized by single crystal X-ray diffraction (CIF files CCDC nos. 943273 (I), 944798 (II)). In complex I, the π-π stacking and C-H⋯π interactions based on the pyridyl group constructed the 1D and 2D structures. While in complex II, various weak interactions including hydrogen bonds (C-H⋯Cl and C-H⋯π) played significant roles in the final supramolecular structures. The luminescent properties of ligand and the complexes were investigated. The results reveal that different anions have shown a great influence on both the molecular structures and luminescent properties of the complexes.
Co-reporter:W. G. Xi;M. D. Yang;L. P. Wang;H. J. Li
Russian Journal of Coordination Chemistry 2014 Volume 40( Issue 10) pp:704-710
Publication Date(Web):2014 October
DOI:10.1134/S107032841410011X
Three new complexes, [CdL2(CH3COO)2(H2O)2] (I), CdL2Br2 (II), CdL2I2 (III), have been successfully synthesized by self-assembly of corresponding metal salts with (E)-2-(3-(4-(1H-imidazole-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile (L). The structures of the complexes were determined by single crystal X-ray diffraction analysis (CIF file CCDC nos. 957831 (I), 957792 (II), 957832 (III)). In complex I, central metal is six-coordinated and the crystal packing shows a 3D supramolecular framework. Complexes II and III display the similar 2D supramolecular structures in which the central metals are four-coordination. The luminescent properties were investigated.
Co-reporter:M. D. Yang;W. G. Xi;J. Zheng;X. Z. Zhang
Russian Journal of Coordination Chemistry 2014 Volume 40( Issue 8) pp:588-593
Publication Date(Web):2014/08/01
DOI:10.1134/S1070328414080120
Two new Zn(II) coordination complexes [ZnL2(SCN)2] (I) and [ZnL2Cl2] (II) have been pre-pared by self-assembly of corresponding metal salts with (E)-2-(3-(4-(1H-imidazole-1-yl)styryl)-5,5-dimethylcyclohexo-2-enylidene) malononitrile (L) and characterized by IR spectrum, elemental analysis and single-crystal X-ray diffraction. Complexes I and II are two-dimensional (2D) networks with different topology structures. The luminescence properties were investigated.
Co-reporter:Zheng Zheng, Qiong Zhang, Zhipeng Yu, Mingdi Yang, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2013 vol. 1(Issue 4) pp:822-830
Publication Date(Web):14 Nov 2012
DOI:10.1039/C2TC00175F
A new series of D–π–A type two-photon absorption (2PA) dyes (1–4) based on imidazo[4,5-f]1,10-phenanthroline have been synthesized and their photophysical properties have been systematically investigated. These dyes showed obvious positive solvatochromic effects mainly due to intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values measured by two-photon excited fluorescence (TPEF) were determined to be 1232 GM and 4752 GM for dye 3 and dye 4, while dyes 1 and 2 do not display 2PA activity. These results demonstrate that their 2PA cross section values (σ) increase with increasing donor/acceptor (D/A) strength of the corresponding molecule. The results also imply that the replacement of the tetrazol group with the aza-crown-ether group results in an opposite charge transfer direction, which has been verified by density functional theory (DFT) calculations. In addition, a two-photon fluorescence cell imaging experiment proved the suitability of dye 3 for this potential application .
Co-reporter:Lianke Wang, Zheng Zheng, Zhipeng Yu, Jun Zheng, Min Fang, Jieying Wu, Yupeng Tian and Hongping Zhou
Journal of Materials Chemistry A 2013 vol. 1(Issue 42) pp:6952-6959
Publication Date(Web):30 Aug 2013
DOI:10.1039/C3TC31626B
Three Schiff bases containing phenylbenzoxazole were synthesized and characterized, which exhibited distinct aggregation-induced enhanced emission (AIEE) behavior in THF–water. However, the single-crystals of L3 show obvious π–π stacking that would induce fluorescent quenching in the solid state. In order to further gain insight into the AIEE mechanism of the three compounds, the size and growth process of particles with different water fractions were studied using SEM, TEM and DLS. The results show that the molecules of compounds can slowly assemble in an ordered fashion to form more-crystalline but less-emissive particles in the THF–water mixtures with low water contents, while in mixtures containing very large amounts of water, the molecules of compounds abruptly agglomerate to form less-crystalline or even amorphous but more-emissive clusters, which effectively avoid π–π stacking.
Co-reporter:Zhipeng Yu, Zheng Zheng, Mingdi Yang, Lianke Wang, Yupeng Tian, Jieying Wu, Hongping Zhou, Hongmei Xu and Zongquan Wu
Journal of Materials Chemistry A 2013 vol. 1(Issue 42) pp:7026-7033
Publication Date(Web):09 Sep 2013
DOI:10.1039/C3TC31506A
Five triphenylamine containing benzimidazole derivatives (a1–a5) with different D/A groups (D and A stand for donor and acceptor, respectively), conjugation length or configuration were designed and synthesized. The one- and two-photon spectroscopic properties of these molecules were studied. All of these compounds have amazing fluorescence quantum yields in the range of 0.39–0.61. Besides, for a1–a5, the λem (emission maximum wavelength of one- and two-photons) are only dominated by the D/A groups, and the conjugation length is irrelevant, implying that the molecular rotation is in the excited-state. To better explain this phenomenon, the structure–property relationships of a1–a5, especially the molecular rotation in the excited-state, have been discussed in detail, and were identified by density functional theory calculations. Furthermore, four azo-heterocycle containing benzimidazole derivatives, which have weak electron-donating ability, were synthesized and discussed as a comparison. Finally, considering their optical action, cytotoxicity and solubility, a1, a2 and a4 were chosen for bio-imaging. The results show that the small molecule a2 is the best candidate for one-photon excited fluorescence and two-photon excited fluorescence imaging.
Co-reporter:Feng Jin, Ying Zhang, Hui-Zhen Wang, Hui-Zhi Zhu, Yan Yan, Jun Zhang, Jie-Ying Wu, Yu-Peng Tian, and Hong-Ping Zhou
Crystal Growth & Design 2013 Volume 13(Issue 5) pp:1978-1987
Publication Date(Web):March 13, 2013
DOI:10.1021/cg400025j
Two multidentate ligands containing a delocalized π-electron system, 2-{5,5-dimethyl-3-[2-(pyridin-3-yl)-ethenyl]cyclohex-2-enylidene}propanedinitrile (L1) and 2-{5,5-dimethyl-3-[2-(pyridin-2-yl)-ethenyl]cyclohex-2-enylidene}propanedinitrile (L2), were synthesized. By self-assembly of the ligands with silver(I) salts, six supramolecular complexes, [Ag(L1)(TsO)(H2O)]2(1), {[Ag3(L1)2(H2O)](ClO4)3}n (2), {[Ag(L1)(NO3)]·0.5C6H6}n (3), {[Ag(L2)(NO3)]·0.5C6H6}n (4), [Ag(L2)2](ClO4) (5), and [Ag(L2)2](PF6) (6), with different structures and topologies were obtained. In polymer 2, L1 acts as a tridentate ligand to bind Ag(I) ions to form a one-dimensional (1D) supramolecular structure. However, when the ligands adopt bidentate coordination modes to coordinate with Ag(I) ions through the pyridyl nitrogen atom and one cyano nitrogen atom, the dinuclear supramolecular complex 1, 1D coordination polymer 3, and two-dimensional (2D) coordination polymer 4 were obtained. In 5 or 6, only the pyridyl nitrogen atom of L2 ligand coordinates with the Ag(I) ion to form a mononuclear complex. The multiple coordination modes of the multidentate ligands and the effect of anions and solvents play important roles in the structural and topological diversity. The luminescent properties were investigated. Compared with the ligands, the complexes show superior luminescent properties with red-shifted and enhanced emission as well as longer fluorescence lifetimes, which indicates that they may be good candidates for optical materials.
Co-reporter:Hongping Zhou, Jianqing Wang, Yixin Chen, Wengang Xi, Zheng Zheng, Donglin Xu, Yuanle Cao, Gang Liu, Weiju Zhu, Jieying Wu, Yupeng Tian
Dyes and Pigments 2013 Volume 98(Issue 1) pp:1-10
Publication Date(Web):July 2013
DOI:10.1016/j.dyepig.2013.01.018
Two novel soluble chemosensors based on Schiff-base diaminomaleonitrile derivatives which were modified by an aza-crown ether moiety have been synthesized. These chemosensors were fully characterized by 1H NMR, 13C NMR spectroscopy, mass spectrometry, IR, DSC and single crystal X-ray diffraction. The recognition abilities of the sensors with a range of metal ions were evaluated and their photophysical properties have been systematically investigated. DFT theoretical calculations were employed to understand the behavior of the sensors toward the Cu(II). The sensing mechanism was derived through experimental and theoretical calculations. The results consistently indicated that the monoaza-10-crown-5 species was the ideal sensor, which can be utilized to monitor Cu(II) in solution over a wide pH range.Highlights► Two new soluble chemosensors were synthesized and fully characterized. ► The recognition abilities of the probes with all kinds of metal ions were tested. ► The detection limit for Cu(II) was 2 × 10−7 when using visible spectroscopy. ► DFT calculations were carried out to understand the behavior of the sensor toward Cu(II). ► The results indicated that the monoaza-10-crown-5 derived chemosensor was ideal for monitoring Cu(II).
Co-reporter:Mingdi Yang, Dongling Xu, Wengang Xi, Lianke Wang, Jun Zheng, Jing Huang, Jingyan Zhang, Hongping Zhou, Jieying Wu, and Yupeng Tian
The Journal of Organic Chemistry 2013 Volume 78(Issue 20) pp:10344-10359
Publication Date(Web):September 19, 2013
DOI:10.1021/jo401719c
Eight triphenylamine (TPA)-based Schiff bases that exhibit different aggregation-induced emission (AIE) or aggregation-caused quenching (ACQ) behavior in tetrahydrofuran (THF)/water mixtures have been synthesized and characterized. The photophysical properties in solution, aqueous suspension, film, and the crystalline state along with their relationships were comparatively investigated. The single-crystal structures of 1–8 indicate that compact π···π stacking or excimers induce fluorescence quenching of 1, 2, 5, and 7. However, the existence of J aggregates or multiple intra- and intermolecular interactions restrict the intramolecular vibration and rotation, enabling compounds 3, 4, 6, and 8 to exhibit good AIE character. The size and growth process of particles with different water fractions were studied using scanning electron microscopy, which demonstrated that smaller uniformly dispersed nanoparticles in the THF/water mixtures favor fluorescence emission. The above results suggest that the combined effects of multiple forces caused by structural variation have a great influence on their molecular packing, electronic structure, and aggregation-induced fluorescence properties. In addition, piezofluorochromic experiments verified the potential applications of 4 and 6.
Co-reporter:Zheng Zheng, Zhipeng Yu, Mingdi Yang, Feng Jin, Qiong Zhang, Hongping Zhou, Jieying Wu, and Yupeng Tian
The Journal of Organic Chemistry 2013 Volume 78(Issue 7) pp:3222-3234
Publication Date(Web):March 18, 2013
DOI:10.1021/jo400116j
A series of new isophorone derivatives (1–5), incorporating the heterocyclic ring or aza-crown-ether group, with large Stokes shifts (>140 nm), have been synthesized and characterized. 1–4 display aggregation-induced emission behaviors, while dye 5 is highly emissive in solution but quenched in the solid state. It was found that the tuning of emission color of the isophorone-based compounds in the solid state could be conveniently accomplished by changing the terminal substituent group. The photophysical properties in solution, aqueous suspension, and crystalline state, along with their relationships, are comparatively investigated. Crystallographic data of 1–4 indicate that the existence of multiple intermolecular hydrogen bonding interactions between the adjacent molecules restricts the intramolecular vibration and rotation and enables compounds 1–4 to emit intensely in the solid state. The size and growth processes of particles with different water fractions were studied using a scanning electron microscope, indicating that smaller globular nanoparticles in aqueous suspension are in favor of fluorescence emissions. The above results suggest that substituent groups have a great influence on their molecular packing, electronic structure, and aggregation-induced emission properties. In addition, fluorescence cell imaging experiment proved the potential application of 5.
Co-reporter:Zhipeng Yu, Yaya Duan, Longhuai Cheng, Zhili Han, Zheng Zheng, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2012 vol. 22(Issue 33) pp:16927-16932
Publication Date(Web):26 Jun 2012
DOI:10.1039/C2JM32405A
Aggregation-induced emission (AIE) compounds, dye2 and dye3, with a rotatable N–N single bond and aza-crown-ether, have been synthesized. The fluorescence intensities of both dyes are very weak in THF, while become extraordinarily strong in a mixture of H2O–THF (v/v 95%). They are increased by 88.9 and 70.7 times, respectively, indicating enhanced blue-green fluorescence emissions. The λem of these two compounds in different states has been well studied. Besides this, dye1 and dye2 were characterized by single crystal X-ray structural determination. The results show that molecular interactions are formed in the particles, which considerably restrict the intramolecular vibration and rotation.
Co-reporter:Fei-Xia Zhou, Zheng Zheng, Hong-Ping Zhou, Wei-Zai Ke, Jian-Qing Wang, Zhi-Peng Yu, Feng Jin, Jia-Xiang Yang, Jie-Ying Wu and Yu-Peng Tian
CrystEngComm 2012 vol. 14(Issue 17) pp:5613-5621
Publication Date(Web):23 May 2012
DOI:10.1039/C2CE25467K
A novel 2,2':6',2′′-terpyridine-based ligand (L) and eight complexes have been synthesized and fully characterized. Six of these complexes ([CdLBr2]2·CHCl3 (2), ZnLI2 (3), [CdLI2]2·CH2Cl2 (4), ZnL(SCN)2·CHCl3 (5), [ZnL2]2(ClO4)4·7H2O (7) and [CdL2](ClO4)2·CH3OH (8)) were determined by single crystal X-ray diffraction analysis. Various weak interactions, including hydrogen bonds (C–H⋯N, C–H⋯X), C–H⋯π and π–π interactions played significant roles in the final supramolecular structures. Linear and nonlinear optical properties of the ligand and eight complexes are described. Experimental results reveal that two-photon absorption (TPA) cross-sections of these complexes are extraordinarily larger than that of the ligand, with maximum values of 97, 661, 787, 218, 133, 613, 230, 384 and 241 GM for L and complexes 1–8 in DMF, respectively. Density functional theory (DFT) calculations were performed on 1–6 and revealed that the halogen affects the accepting capability of surrounding metals due to different electron inductive effects, in the order Br > SCN > I. Thus, this in turn affects the TPA cross-section values. The results indicate that the TPA cross-sections vary in the order Br > SCN > I, which is consistent with the experimental results.
Co-reporter:Feng Jin, Xiao-Fei Yang, Sheng-Li Li, Zheng Zheng, Zhi-Peng Yu, Lin Kong, Fu-Ying Hao, Jia-Xiang Yang, Jie-Ying Wu, Yu-Peng Tian and Hong-Ping Zhou
CrystEngComm 2012 vol. 14(Issue 24) pp:8409-8417
Publication Date(Web):25 Sep 2012
DOI:10.1039/C2CE26145F
A new multidentate ligand containing pyridyl and pyrazolyl groups, 6-phenyl-4-(4-(1H-pyrazolyl)phenyl)-2,2′-bipyridine (L) was designed and synthesized. By self-assembly of L with silver(I) salts, three new complexes containing disilver(I) metallocycles, namely [TsOAgL]2 (1), [AgL]2(ClO4)2 (2) and [AgL2]2(NO3)2[AgLNO3]2·(H2O)2 (3), were obtained. Polymorph (II) of L was obtained unexpectedly when AgSCN complex was prepared. In complexes 1 and 2, two ligands in a head-to-tail mode bridge two Ag(I) ions via pyridyl and pyrazolyl N atoms to generate binuclear [AgL]2 unit. While, in complex 3, the asymmetric unit contains two kinds of crystallographically and conformationally independent molecules with completely different structures and coordination environments of Ag(I) ions. The structure of one kind of molecule is similar to that of complex 1. However, the other kind has a uninuclear structure, and the Ag(I) center is coordinated by four pyridyl nitrogen atoms from two ligands. Different anions have shown a great influence on both the molecular structures and the packing structures of the complexes. The nonlinear optical (NLO) properties of L and the complexes were measured through Z-scan technique. The results show that they may be good candidates for non-linear optical materials.
Co-reporter:Hongping Zhou, Zheng Zheng, Guoyi Xu, Zhipeng Yu, Xiaofei Yang, Longhuai Cheng, Xiaohe Tian, Lin Kong, Jieying Wu, Yupeng Tian
Dyes and Pigments 2012 Volume 94(Issue 3) pp:570-582
Publication Date(Web):September 2012
DOI:10.1016/j.dyepig.2012.03.017
A series of new one, two and three-branched two-photon absorption triazine dyes containing triphenylamine with a π-bond and a σ-electron pair as a bridge, and different electron-donating groups, have been synthesized and their photophysical properties have been systematically investigated. These dyes showed obvious solvatochromic effects, i.e., significant bathochromic shifting of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to intramolecular charge-transfer (ICT). The two-photon absorption (2PA) cross section values were determined by two-photon excited fluorescence (TPEF) measurements in DMF. This result further proved that a σ-electron pair as a bridge is an efficient way to transfer charge as well as a π bridge to provide a large 2PA cross section, and that their 2PA cross section values (δ) increase with increasing electron-donating strength of the end group and branch number. In addition, two-photon fluorescence cell imaging of dye 7a in HeLa and MCF-7 cancer cells was demonstrated.Highlights► We designed and synthesized six two-photon absorption triazine dyes. ► Six dyes contain triphenylamine with a π-bond and a σ-electron pair as bridge. ► Linear and nonlinear optical properties of six dyes were investigated. ► Two-photon fluorescence cell imaging of dye 7a were demonstrated. ► The results revealed that σ-electron pair as bridge can also induce the large δ.
Co-reporter:Hongping Zhou, Jianqing Wang, Feixia Zhou, Dongling Xu, Yuanle Cao, Gang Liu, Lin Kong, Jiaxiang Yang, Jieying Wu, Yupeng Tian
Dyes and Pigments 2012 Volume 95(Issue 3) pp:723-731
Publication Date(Web):December 2012
DOI:10.1016/j.dyepig.2012.07.005
A simple D-π-A type ligand (L: 4′-(4-[4-(1H-[1,2,4]-triazolyl)styryl]phenyl)-2,2′:6′,2″-terpyridine) was designed and synthesized, which reacted with HgX2 (X = Cl, Br, I, SCN) yielding a series of uncommon five-coordinated mercury (II) complexes (Dyes 1–4). The ligand and Dye 4 were characterized by single crystal X-ray diffraction determination. Linear and nonlinear optical properties of the ligand and dyes were exhibited. Experimental results revealed that the two-photon absorption (TPA) cross-sections of the four dyes are considerably larger than that of the ligand. Density function theory (DFT) calculations performed on Dyes 1–4 showed that the halogens affect the accepting capability of the complexed metal due to different electron inductive effects, which finally influence the TPA cross-section values.Highlights► A simple ligand and its complexes based on Hg (II) salts were synthesized. ► The topological structures of L and Dye 4 were systematically studied. ► Linear and nonlinear optical properties of L and four dyes were investigated. ► DFT calculations were performed to evaluate the effect of anions on δTPA. ► The results revealed that the dyes have much larger δTPA.
Co-reporter:Hongping Zhou, Feixia Zhou, Shiya Tang, Peng Wu, Yixin Chen, Yulong Tu, Jieying Wu, Yupeng Tian
Dyes and Pigments 2012 Volume 92(Issue 1) pp:633-641
Publication Date(Web):January 2012
DOI:10.1016/j.dyepig.2011.06.028
Four novel dyes are prepared by thiophene as π bridge between carbazole central core and other terminal groups by Suzuki and Heck coupling reactions. These dyes are fully characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. Linear absorption, single- and two-photon excited fluorescence in various solvents are experimentally investigated. The calculated two-photon absorption cross sections of 9-Hexyl-3,6-di((5-phenyl)-2-thienyl)carbazole (1), 9-Hexyl-3,6-di((5-thienyl)-2-thienyl)carbazole (2), 9-Hexyl-3,6-di((5-p-vinylpyridyl)-2-thienyl)-carbazole (3) and 9-Hexyl-3,6-di-((5-o-vinylpyridyl)-2-thienyl)carbazole (4) for the lowest excited state are 537.84, 550.76, 1292.95 and 1340.40 × 10−50 cm4 s photon−1, respectively. Calculated and experimental data have shown that thiophene as π electron bridge improves the two-photon absorption cross sections greatly. Two-photon optical data recording experiments have been carried out at 820 nm laser radiation.Highlights► Four novel dyes are prepared by Thiophene as π electron Bridge. ► These dyes are characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. ► They improve the two photons absorption cross sections greatly. ► Two-photon optical data show the novel dyes exhibit good optical memory.
Co-reporter:Feng Jin, Fei-Xia Zhou, Xiao-Fei Yang, Long-Huai Cheng, Ya-Ya Duan, Hong-Ping Zhou, Lin Kong, Fu-Ying Hao, Jie-Ying Wu, Yu-Peng Tian
Polyhedron 2012 Volume 43(Issue 1) pp:1-7
Publication Date(Web):13 August 2012
DOI:10.1016/j.poly.2012.04.001
Three new complexes [Zn(NCS)2L2] (1), [Hg(SCN)2L2] (2) and [Mn(NCS)2L4] (3), have been synthesized by the self-assembly of 4-imidazolychalcone (abbreviated as L) with M(SCN)2 (M = Hg2+, Zn2+, Mn2+). The complexes have been characterized by spectroscopic and crystallographic methods. 1H NMR spectra of complexes 1–3 present that metal ions have effect on the chemical shifts of protons of coordinated groups. Three complexes illustrate different molecular structures due to the different coordinated modes of the metal ions. In the title complexes, the coordination geometries of Zn, Hg and Mn ions are tetrahedral N4, N2S2 and octahedral N6, respectively. Finally, hydrogen bonding interactions assemble the different coordination units into higher-dimensional frameworks. The results show that the metal ion and weak non-covalent interactions play important roles in the construction of the final supramolecular structures.Graphical abstractThree different structural supramolecular complexes based on the reaction of 4-imidazolychalcone and M(SCN)2 (M = Hg2+, Zn2+, Mn2+) were synthesized by self-assembling. The complexes have been characterized by spectroscopic and crystallographic methods. 1H NMR spectra of complexes 1–3 present that metal ions have effect on the resonances of the protons of coordinated groups. The results show that the coordination geometries of Zn, Hg and Mn ions are tetrahedral N4, N2S2 and octahedral N6, respectively. The complexes illustrate different molecular structures due to the different coordinated modes of the metal ions. Finally, higher-dimensional supramolecular structures are formed through different weak non-covalent interactions.Highlight► A new ligand containing imidazolyl and carbonyl groups was synthesized and fully characterized. ► Three complexes based on reaction of the ligand and M(SCN)2 (M = Hg2+, Zn2+, Mn2+) were synthesized. ► The complexes were characterized by spectroscopic and crystallographic methods. ► 1H NMR spectra show metal ions have effect on the resonances of the protons of coordinated groups. ► Higher-dimensional structures are formed through coordinate bonds and weak non-covalent forces.
Co-reporter:Zheng Zheng, Hong-ping Zhou, Guo-yi Xu, Zhi-peng Yu, Xiao-fei Yang, Long-huai Cheng, Lin Kong, Yan Feng, Jie-ying Wu, Yu-peng Tian
Tetrahedron 2012 68(32) pp: 6569-6574
Publication Date(Web):
DOI:10.1016/j.tet.2012.05.050
Co-reporter:Wen-Qian Geng, Hong-Ping Zhou, Long-Huai Cheng, Fu-Ying Hao, Guo-Yi Xu, Fei-Xia Zhou, Zhi-Peng Yu, Zheng Zheng, Jian-Qing Wang, Jie-Ying Wu, Yu-Peng Tian
Polyhedron 2012 31(1) pp: 738-747
Publication Date(Web):
DOI:10.1016/j.poly.2011.10.032
Co-reporter:DongMei Li;Qiong Zhang;A. M. Showkot Hossain;Mei Sun
Science China Chemistry 2011 Volume 54( Issue 5) pp:730-736
Publication Date(Web):2011 May
DOI:10.1007/s11426-010-4141-6
Three bis-vinylpyridine compounds (4,4′-bis(2-vinylpyridine)biphenyl L1, 4,4′-bis(3-vinylpyridine) biphenyl L2, and 4,4′-bis (4-vinylpyridine)biphenyl L3) were synthesized by one-step solid-state reactions at room temperature, giving nearly quantitative yields. The compounds obtained were fully characterized by IR, MS and NMR spectroscopies. The structures of L2 and L3 were determined by single crystal X-ray diffraction analysis. No noticeable solvatochromism was observed in either one-photon absorption or one-photon excited fluorescence spectra. All of the compounds have high fluorescence quantum yields and long fluorescence lifetime. The linear and nonlinear optical properties of the compounds were investigated both experimentally and theoretically. Interestingly, the position of the nitrogen atom from pyridine influences their two-photon absorption across-sections.
Co-reporter:Hong-Ping Zhou, Xiao-Ping Gan, Xian-Lei Li, Zhao-Di Liu, Wen-Qian Geng, Fei-Xia Zhou, Wei-Zai Ke, Peng Wang, Lin Kong, Fu-Ying Hao, Jie-Ying Wu and Yu-Peng Tian
Crystal Growth & Design 2010 Volume 10(Issue 4) pp:1767-1776
Publication Date(Web):March 10, 2010
DOI:10.1021/cg901453a
A series of new five-coordinated mercury(ΙΙ) coordination complexes (Hg(TpzT)(SCN)2·H2O (1), Hg(TpzT)I2·H2O (2), Hg(TpzT)Br2·H2O (3), 2Hg(TpzT)Cl2·HgCl2·2H2O (4)) have been synthesized by self-assembling the flexible ligand 2,4,6-tri(pyrazole-1-yl)-1,3,5-triazine (TpzT) with HgX2 (X = SCN, I, Br, Cl). Various weak interactions including hydrogen bonds (O−H···X, C−H···X), π−π interactions, and S···S contacts play significant roles in the final topological structures of the four compounds. Unexpectedly, 5 and 6 were obtained accidentally by self-assembling TpzT with MX2 (Zn(NO3)2·6H2O or CdI2) in methanol and were assessed by X-ray crystallography, which indicated that there are nucleophilic substitution reactions. Surprisingly, all the Hg−N bonds of approximately 2.70 Å in length formed by the tridentate ligand and mercuric salt are rather unusual. So density functional theory (DFT) calculations (Amsterdam density functional, ADF) were employed to study the bond dissociation energies (BDE) of Hg−N bonds in 1−4 to assess the nature of the bonds. The calculation reveals the strong coordination nature of Hg−N bonds in 1−4 compared to that of the same coordination mode of compound A ((4′-(4-[4-(imidazole)phenylethylene]phenyl)-2,2′:6′,2′′-terpyridine)HgBr2·CHCl3) with the normal range Hg−N bond lengths. And a similar trend is that the larger the anion and BDE become, the steadier the coordination complexes are.
Co-reporter:Wen-Qian Geng, Xian-Lei Li, Jian-Hui Yin, Hong-Ping Zhou, Jie-Ying Wu, Yu-Peng Tian
Inorganic Chemistry Communications 2010 Volume 13(Issue 11) pp:1285-1288
Publication Date(Web):November 2010
DOI:10.1016/j.inoche.2010.07.017
A new coordination polymer 1 [CdL2(NO3)2]n (L: 3, 6-di-(1, 2, 4-triazole-1-yl)-N-ethylcarbazole) has been synthesized by self-assembly reaction and characterized by elemental analysis and IR spectroscopy. The single-crystal X-ray diffraction shows that the [CdL2(NO3)2]n crystallizes in the monoclinic system and C2/m space group and the Cd(II) atom is four-coordinated. The coordination polyhedron can be described as a rectangle which is rather infrequent. The coordination bonds, hydrogen bonds and π–π interactions shaped the 3D network structure. A possible formation mechanism was discussed. The optical property was also studied.The [CdL2(NO3)2]n crystallizes in the monoclinic system and C2/m space group and the Cd(II) atom is four-coordinated. The coordination polyhedron can be described as a rectangle which is rather infrequent. The coordination bonds, hydrogen bonds and π–π interactions shaped the 3D network structure. The solid-state fluorescent property was investigated at room temperature.
Co-reporter:Lin Kong, Wei-Jie Li, Xian-Lei Li, Wen-Qian Geng, Fu-Ying Hao, Jie-Ying Wu, Hong-Ping Zhou, Jia-Xiang Yang, Yu-Peng Tian, Bao-Kang Jin
Polyhedron 2010 29(6) pp: 1575-1582
Publication Date(Web):
DOI:10.1016/j.poly.2010.02.018
Co-reporter:Hong-Ping Zhou, Jian-Hui Yin, Ling-Xia Zheng, Peng Wang, Fu-Ying Hao, Wen-Qian Geng, Xiao-Ping Gan, Guo-Yi Xu, Jie-Ying Wu, Yu-Peng Tian, Xu-Tang Tao, Min-Hua Jiang and Yu-He Kan
Crystal Growth & Design 2009 Volume 9(Issue 8) pp:3789
Publication Date(Web):June 25, 2009
DOI:10.1021/cg900520j
Self-assembly of the flexible ligand 3,6-di-(1,2,4-triazole-1-yl)-N-alkylcarbazole with HgX2 (X = I, Br, Cl, SCN) yielded a short series of new coordination polymer complexes (1, 3−6) with double-helical, “W”, and single molecular structure of complex 2. Weak interactions, including hydrogen bonds, π−π interactions, M···X bonds, and counteranions play significant roles in the final crystal structures. Three different DFT calculations are performed on the weak interaction between the two helical chains from the four different coordination polymers (complexes 1, 4, 5 and 6). The outcomes show a similar trend, the larger the halogen anion, the weaker the interaction between the infinite chains, which provides useful information on the thermal stable properties of the infinite double-helical polymer chains.
Co-reporter:Dongmei Li, Liangfei Lv, Pingping Sun, Wen Zhou, Peng Wang, Jieying Wu, Yuhe Kan, Hongping Zhou, Yupeng Tian
Dyes and Pigments 2009 Volume 83(Issue 2) pp:180-186
Publication Date(Web):November 2009
DOI:10.1016/j.dyepig.2009.04.006
Two blue emitters, 3,7-bis(5′-(trifluoromethyl)-1′H-pyrazole-3′-yl)10-ethylphenothiazine and 3,7-bis(5′-(phenyl)-1′H-pyrazole-3′-yl)10-ethyl-phenothiazine and one red, bis-dioxaborine emitter, each based on two, yellow-green emitting, bis-β-diketonate, phenothiazine derivatives, were obtained in high yield and characterized. Systematic investigation of the two-photon absorption characteristics was carried out using one-photon absorption, one-photon excited fluorescence as well as two-photon excited fluorescence spectra. TDDFT computational studies were undertaken to secure an insight into the nature of the compounds' electrochemical and photophysical properties. Low-energy absorption transmissions resemble those observed for the experimental one-photon absorption spectra.
Co-reporter:Dongmei Li;Rentao Hu;Wen Zhou;Pingping Sun;Yuhe Kan;Yupeng Tian;Hongping Zhou;Jieying Wu;Xutang Tao;Minhua Jiang
European Journal of Inorganic Chemistry 2009 Volume 2009( Issue 18) pp:2664-2672
Publication Date(Web):
DOI:10.1002/ejic.200900216
Abstract
(E)-3-(10-ethylphenothiazine-3-yl)acrylic acid (LCOOH) was synthesized. LCOOH reacted with Ph3Sn(OH) and nBu2SnO to afford Ph3SnO2CL (1) and {[nBu2SnO2CL]2O}2 (2), respectively. The structures of all the compounds were solved by single-crystal X-ray diffraction. Compounds 1 and 2 present discrete and ladder frameworks, respectively. The one-photon absorption and excited fluorescence, and two-photon excited fluorescence spectra of all the compounds were systematically investigated. The results show that the two organostannoxanes exhibit much more enhanced two-photon absorption properties than LCOOH. TDDFT computational studies have been performed to elucidate the electronic structures of the ground state of LCOOH.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Co-reporter:Hong-Ping Zhou, Peng Wang, Ling-Xia Zheng, Wen-Qian Geng, Jian-Hui Yin, Xiao-Ping Gan, Guo-Yi Xu, Jie-Ying Wu, Yu-Peng Tian, Yu-He Kan, Xu-Tang Tao and Min-Hua Jiang
The Journal of Physical Chemistry A 2009 Volume 113(Issue 11) pp:2584-2590
Publication Date(Web):February 23, 2009
DOI:10.1021/jp810565w
By combining a large π-conjugated bidentate ligand L: 3,6-dipyrazole-N-ethylcarbazole with HgI2, an extraordinary supramolecular coordination polymer, [Hg4L2I8]∞, has been prepared. The crystal structures of the ligand and its coordination polymer were determined by X-ray crystallography, which shows three varied coordination modes especially the rare asymmetric quadruply bridged trinuclear moieties in [Hg4L2I8]∞. Density functional theory (DFT) calculations (ADF) performed on model dimers show the roles of covalent and noncovalent interactions in establishing the three-dimensional architecture.
Co-reporter:XuChun Wang;JieYing Wu;HongPing Zhou;YuPeng Tian
Science China Chemistry 2009 Volume 52( Issue 7) pp:930-936
Publication Date(Web):2009 July
DOI:10.1007/s11426-009-0091-2
Two new metal-centered ferrocene complexes Ni(SCN)2(L)4 (1) and Cu(OAc)2(L)2 (2) (L = 1-[1-ferrocenylmethyl]imidazole) have been synthesized and characterized by elemental analysis, single crystal X-ray diffraction analysis, spectroscopic and cyclic voltammetric measurements. The geometry of Ni(II) in 1 is octahedral, with four ligands in the equatorial plan and two thiocyanate anions at the axial site, while that of Cu(II) in 2 is a distorted octahedron formed by two chealted OAc− and two ligands. Single crystal X-ray diffraction studies reveal that there is partial electron delocalization from ferrocene to imidazole in the two complexes. Electrochemical measurements exhibit that complexes 1 and 2 undergo similar reversible one electron redox processes, suggesting that the ferrocene moieties are equivalent and there are no interactions among them.
Co-reporter:Mei Sun, Peng Wang, Hongping Zhou, Jiaxiang Yang, Jieying Wu, Yupeng Tian, Xutang Tao, Minhua Jiang
Journal of Molecular Structure 2008 Volume 873(1–3) pp:73-78
Publication Date(Web):17 February 2008
DOI:10.1016/j.molstruc.2007.03.019
Two novel 1D infinite chain coordination polymers, [CdL(NO3)2]n and [CoL(NO3)2]n (L = 4,4′-bis[2-(2-pyridyl)ethenyl]biphenyl) have been prepared by reacting Cd(NO3)2 and Co(NO3)2 with the novel ligand L. Complexes 1 and 2 have been characterized by elemental analysis, IR and single crystal X-ray diffraction determination. The metal ions in the polymers have six coordinate pseudo octahedral structures with two pyridyl nitrogen atoms of L and four oxygen atoms of nitrate. The ligand coordinates to metal ions forming bridges in different geometries (cis and trans coordination modes). The results of TGA determination show that the coordination polymers are quite thermally stable. The complexes exhibit a strong emission band with the maximum intensity at 524 and 545 nm in solid-state, respectively, upon excitation at 350−450 nm.
Co-reporter:Hong-Ping Zhou;Peng Wang;Zhang-Jun Hu;Lin Li;Jing-Jin Chen;Yang Cui;Yu-Peng Tian;Jie-Ying Wu;Jia-Xiang Yang;Xu-Tang Tao;Min-Hua Jiang
European Journal of Inorganic Chemistry 2007 Volume 2007(Issue 13) pp:
Publication Date(Web):20 MAR 2007
DOI:10.1002/ejic.200600887
Two functional, flexible ligands, namely 3,6-dipyrazolyl-9-ethylcarbazole (L1) and 3,6-diimidazolyl-9-ethylcarbazole (L2) have been synthesized and characterized and their coordination to various AgI, CdII, and CoII salts investigated. Six new complexes, 1–6, have been obtained and fully characterized by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction. The 2D double helix framework of the complex [CdL1I2]n (1) is formed by C–H···I hydrogen bonds, whereas the same 2D double helix framework of compound [{AgL1SO3PhCH3}2(CH3OH)(H2O)]n (2) is formed by S–O···H and C–H···O hydrogen bonds and weak π–π interactions. The coordination modes of CdII and CoII in [CdL22(NCS)2]n (3), [CoL22(NCS)2(CHCl3)2]n (4), [CdL22(NO3)2(CH3OH)2]n (5), and [CoL22(NO3)2(CH3OH)2]n (6) are the same, but in the packing diagram interlayers form a 3D network through C–H···S interactions and π–π interactions in 3, interlayers form a 3D network through S···S interactions and π–π interactions in 4, novel 3D structures are formed by interchain O···H–C hydrogen bonding and interlayer O···H–C hydrogen-bonding and π–π interactions in 5 and 6. The structural differences between these complexes show the influence of the orientation of the coordinating group of the ligand. These results also show that the metal ion, anion, and nonbonding and π–π interactions are significant factors in controlling the structural topology of these metal-organic supramolecular architectures. In addition, the luminescence properties of L1, 1, L2, and 3 are investigated in the solid state at room temperature. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Co-reporter:Hong-ping Zhou, Dong-mei Li, Peng Wang, Le-hua Cheng, Yuan-hao Gao, Yong-min Zhu, Jie-ying Wu, Yu-peng Tian, Xu-tang Tao, Min-hua Jiang, Hoong-Kun Fun
Journal of Molecular Structure 2007 Volume 826(2–3) pp:205-210
Publication Date(Web):29 January 2007
DOI:10.1016/j.molstruc.2006.05.003
A new bidentate Schiff base ligand (abbreviated as L) derived from the condensation of S-methyldithiocarbazate (SMDTC) with 9-fluorenone, and its complexes ML2 (M = Ni(II), Zn(II) and Pd(II)) have been synthesized and fully characterized by elemental analyses, IR, molar conductivity and UV–vis spectroscopy. The structures of complexes ZnL2 and PdL2 have been determined by X-ray diffraction analysis. Complex ZnL2 adopts a distorted tetrahedral geometry with the azomethine nitrogen atom and the thiolate sulfur atom. The coordination geometry about the Pd(II) is surprisingly a cis-configuration square-planar formed by the Pd(II) atom coordinating to the NS bidentate ligand. Detailed crystal structure analyses show that the cis-positioning of the two ligands was stabilized by the π–π stacking interactions between the two delocalized diazafluorene moieties. The two-photon absorption of L and ML2 solutions (in DMF) was measured at 532 nm by the open-aperture Z-scan technique.
Co-reporter:Hong-Ping Zhou, Dong-Mei Li, Ju-Zhou Zhang, Yong-Min Zhu, Jie-Ying Wu, Zhang-Jun Hu, Jia-Xiang Yang, Gui-Bao Xu, Yu-Peng Tian, Yi Xie, Xu-Tang Tao, Min-Hua Jiang, Li-Min Tao, Ya-Hui Guo, Chuan-Kui Wang
Chemical Physics 2006 Volume 322(Issue 3) pp:459-470
Publication Date(Web):20 March 2006
DOI:10.1016/j.chemphys.2005.09.045
Abstract
Three novel A–π–D–π–A type compounds 3,6-bis[2-(4-pyridyl)ethenyl]-9-ethylcarbazole (1), 3,6-bis[2-(2-pyridyl)ethenyl]-9-ethylcarbazole (2), 3,6-bis[2-(4-pyridyl)ethenyl]-9-ethylpyridylcarbazole (3) were conveniently synthesized by Pd-catalyzed Heck coupling methodology and characterized by single crystal X-ray diffraction determination. One-photon fluorescence, one-photon fluorescence quantum yields, one-photon fluorescence lifetime, and two-photon fluorescence have been investigated. The calculated two-photon absorption cross-sections for the three initiators by quantum chemical method are as high as 947, 943 and 815 × 10−50 cm4 s photon−1, respectively. Two-photon initiating polymerization microfabrication experiments have been carried out and the possible polymerization mechanism was also discussed. The results show that they are good two-photon absorbing chromophores and effective two-photon photopolymerization initiators.
Co-reporter:Lianke Wang, Yanfang Shen, Mingdi Yang, Xiuzhen Zhang, Weinan Xu, Qiuju Zhu, Jieying Wu, Yupeng Tian and Hongping Zhou
Chemical Communications 2014 - vol. 50(Issue 63) pp:NaN8726-8726
Publication Date(Web):2014/05/19
DOI:10.1039/C4CC02564D
Fibrous nanoaggregates of a new benzoxazole-based derivative have been reported. This derivative exhibits not only H-aggregates but also strong yellow fluorescence, which is different from the traditional understanding of H-aggregates.
Co-reporter:Lianke Wang, Hongping Zhou, Jieying Wu and Yupeng Tian
Dalton Transactions 2015 - vol. 44(Issue 21) pp:NaN9926-9926
Publication Date(Web):2015/04/17
DOI:10.1039/C5DT01090J
Copper complexes have been frequently involved in many Cu-mediated carbon–hydrogen halogenation reactions. We fortunately obtained three different valence benzoxazolyl–copper complexes, along with aryl carbon–hydrogen bromination, in the self-assembly reaction of ligands with CuBr2. The complexes have been successfully characterized by X-ray single crystal diffraction analyses. The results indicate that 1 consists of di-brominated p-benzoxazolylphenylamine (L) and an unusual high valence copper(III) complex with tetrahedral geometry, 2 is the first polymeric catenulate di-brominated benzoxazolyl-copper(I) complex and 3 is the mono-brominated benzoxazolyl–copper(II) complex. We speculate proposed mechanisms for the formation of these complexes and the bromination of aryl carbon–hydrogen based on these crystal structures.
Co-reporter:Xinping Ge, Xiaoping Gan, Shun Yao, Kang Wang, Weiju Zhu, Jianhua Yu, Jieying Wu, Yupeng Tian and Hongping Zhou
Journal of Materials Chemistry A 2016 - vol. 4(Issue 16) pp:NaN2793-2793
Publication Date(Web):2016/03/22
DOI:10.1039/C6TB00201C
A new series of benzoxazole-based two-photon absorption (2PA) chromophores (T1–5) were synthesized and fully characterized. Among them, T1–3 are linear donor (D)–π–acceptor (A) type fluorophores with various electron-donating groups, while T4 and T5 are multi-branched compounds stemming from T3. Their photophysical properties have been systematically investigated, and the two-photon absorption properties indicate that the highest 2PA cross-section (σ2PA) is 2702 GM for T5 (in DMF). Structure–property relationships of the chromophores are comprehensively discussed based on their optical properties, crystal structures and density functional theory (DFT) calculations. In addition, a two-photon fluorescence cell imaging experiment demonstrates the potential bio-application of T1–5 with good photostability and low cytotoxicity.
Co-reporter:Mingdi Yang, Yan Zhang, Weiju Zhu, Huizhen Wang, Jing Huang, Longhuai Cheng, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2015 - vol. 3(Issue 9) pp:NaN2002-2002
Publication Date(Web):2014/12/24
DOI:10.1039/C4TC02616K
Three new anthryl Schiff base derivatives containing a similar molecular structure were synthesized through a simple method and their fluorescent properties were investigated in detail. Among these, compound 1 displayed an aggregation-induced emission (AIE) feature, 2 exhibited an aggregation-induced emission enhancement (AIEE) property, while 3 showed aggregation-caused quenching (ACQ) behavior. Single-crystal structure and theoretical calculation analysis show that the larger conjugation and the existence of multiple intra- and intermolecular interactions restricts the intramolecular vibration and rotation, which benefit the emission in the condensed state, while the tight dimer structure and intramolecular torsional motion induce fluorescence quenching. Moreover, compound 2 can be utilized as fluorescence on–off type sensor for Cu2+ in methanol–H2O (4/1, v/v, pH 7.2) HEPES buffer solution, as well as fluorescence off–on type sensor for Zn2+ in pure methanol solution. The 2:1 ligand-to-metal coordination pattern of the 2-Cu2+ and 2-Zn2+ were calculated through a Job's plot, and were further confirmed by X-ray crystal structures of complexes 2-CuBr2 and 2-ZnCl2. In addition, 2 also exhibits a piezofluorochromic characteristic.
Co-reporter:Yuanle Cao, Mingdi Yang, Yang Wang, HongPing Zhou, Jun Zheng, Xiuzhen Zhang, Jieying Wu, Yupeng Tian and Zongquan Wu
Journal of Materials Chemistry A 2014 - vol. 2(Issue 19) pp:NaN3694-3694
Publication Date(Web):2014/02/12
DOI:10.1039/C3TC32551B
A new Schiff-base family containing [4-(1H-benzimidazole-2-yl)-phenyl]-bis-(4-ethoxy-phenyl)-amine has been synthesized through a condensation reaction. All the derivatives possess properties of aggregation-induced and crystallization-enhanced emission (AIE and CEE), which show time-dependent characteristics at a concentration of 10 μM and are studied in detail by scanning electron microscope (SEM) and transmission electron microscope (TEM). Different aggregation forms and the growth of crystals of the compounds, could be responsible for the notably different degrees of fluorescence enhancement.
Co-reporter:Gang Liu, Mingdi Yang, Lianke Wang, Jun Zheng, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2014 - vol. 2(Issue 15) pp:NaN2691-2691
Publication Date(Web):2014/01/28
DOI:10.1039/C3TC32591A
Three new Schiff base derivatives possessing vagarious blue aggregation-induced emission (AIE) characteristics in tetrahydrofuran (THF)–water were synthesized. Their photophysical properties in solution, aqueous suspension, film and crystalline states, along with their relationships, were comparatively investigated. The crystallographic data for dye 1 and dye 3 indicated that the existence of multiple intermolecular hydrogen bonding interactions restricted intramolecular vibration and rotation. Moreover, the sizes and growth processes of particles with different water fractions were studied using a scanning electron microscope (SEM) and dynamic light scattering (DLS). The results showed that the small homogeneous particles, assembled in an ordered fashion with appropriate water contents, exhibited distinct AIE behavior. Moreover, in a THF–H2O (4:1, v/v) solution of HEPES (20 mM) buffer, dye 2 showed fluorescence turn-on sensing towards Cr3+ and Al3+via chelation enhanced fluorescence (CHEF). The 2:1 stoichiometries of the sensor complexes (dye 2–Cr3+ and dye 2–Al3+) were calculated from Job plots based on fluorescence titrations.
Co-reporter:Zheng Zheng, Qiong Zhang, Zhipeng Yu, Mingdi Yang, Hongping Zhou, Jieying Wu and Yupeng Tian
Journal of Materials Chemistry A 2013 - vol. 1(Issue 4) pp:NaN830-830
Publication Date(Web):2012/11/14
DOI:10.1039/C2TC00175F
A new series of D–π–A type two-photon absorption (2PA) dyes (1–4) based on imidazo[4,5-f]1,10-phenanthroline have been synthesized and their photophysical properties have been systematically investigated. These dyes showed obvious positive solvatochromic effects mainly due to intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values measured by two-photon excited fluorescence (TPEF) were determined to be 1232 GM and 4752 GM for dye 3 and dye 4, while dyes 1 and 2 do not display 2PA activity. These results demonstrate that their 2PA cross section values (σ) increase with increasing donor/acceptor (D/A) strength of the corresponding molecule. The results also imply that the replacement of the tetrazol group with the aza-crown-ether group results in an opposite charge transfer direction, which has been verified by density functional theory (DFT) calculations. In addition, a two-photon fluorescence cell imaging experiment proved the suitability of dye 3 for this potential application .
Co-reporter:Lianke Wang, Zheng Zheng, Zhipeng Yu, Jun Zheng, Min Fang, Jieying Wu, Yupeng Tian and Hongping Zhou
Journal of Materials Chemistry A 2013 - vol. 1(Issue 42) pp:NaN6959-6959
Publication Date(Web):2013/08/30
DOI:10.1039/C3TC31626B
Three Schiff bases containing phenylbenzoxazole were synthesized and characterized, which exhibited distinct aggregation-induced enhanced emission (AIEE) behavior in THF–water. However, the single-crystals of L3 show obvious π–π stacking that would induce fluorescent quenching in the solid state. In order to further gain insight into the AIEE mechanism of the three compounds, the size and growth process of particles with different water fractions were studied using SEM, TEM and DLS. The results show that the molecules of compounds can slowly assemble in an ordered fashion to form more-crystalline but less-emissive particles in the THF–water mixtures with low water contents, while in mixtures containing very large amounts of water, the molecules of compounds abruptly agglomerate to form less-crystalline or even amorphous but more-emissive clusters, which effectively avoid π–π stacking.
Co-reporter:Zhipeng Yu, Zheng Zheng, Mingdi Yang, Lianke Wang, Yupeng Tian, Jieying Wu, Hongping Zhou, Hongmei Xu and Zongquan Wu
Journal of Materials Chemistry A 2013 - vol. 1(Issue 42) pp:NaN7033-7033
Publication Date(Web):2013/09/09
DOI:10.1039/C3TC31506A
Five triphenylamine containing benzimidazole derivatives (a1–a5) with different D/A groups (D and A stand for donor and acceptor, respectively), conjugation length or configuration were designed and synthesized. The one- and two-photon spectroscopic properties of these molecules were studied. All of these compounds have amazing fluorescence quantum yields in the range of 0.39–0.61. Besides, for a1–a5, the λem (emission maximum wavelength of one- and two-photons) are only dominated by the D/A groups, and the conjugation length is irrelevant, implying that the molecular rotation is in the excited-state. To better explain this phenomenon, the structure–property relationships of a1–a5, especially the molecular rotation in the excited-state, have been discussed in detail, and were identified by density functional theory calculations. Furthermore, four azo-heterocycle containing benzimidazole derivatives, which have weak electron-donating ability, were synthesized and discussed as a comparison. Finally, considering their optical action, cytotoxicity and solubility, a1, a2 and a4 were chosen for bio-imaging. The results show that the small molecule a2 is the best candidate for one-photon excited fluorescence and two-photon excited fluorescence imaging.
Co-reporter:Zhipeng Yu;Yaya Duan;Longhuai Cheng;Zhili Han;Zheng Zheng;Hongping Zhou;Jieying Wu;Yupeng Tian
Journal of Materials Chemistry A 2012 - vol. 22(Issue 33) pp:NaN16932-16932
Publication Date(Web):2012/07/31
DOI:10.1039/C2JM32405A
Aggregation-induced emission (AIE) compounds, dye2 and dye3, with a rotatable N–N single bond and aza-crown-ether, have been synthesized. The fluorescence intensities of both dyes are very weak in THF, while become extraordinarily strong in a mixture of H2O–THF (v/v 95%). They are increased by 88.9 and 70.7 times, respectively, indicating enhanced blue-green fluorescence emissions. The λem of these two compounds in different states has been well studied. Besides this, dye1 and dye2 were characterized by single crystal X-ray structural determination. The results show that molecular interactions are formed in the particles, which considerably restrict the intramolecular vibration and rotation.
Co-reporter:Hong Li, Ruilong Zhang, Chunxia Li, Bei Huang, Tingting Yu, Xiaodan Huang, Xuanjun Zhang, Fei Li, Hongping Zhou and Yupeng Tian
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 3) pp:NaN604-604
Publication Date(Web):2016/11/28
DOI:10.1039/C6OB02384C
A triphenylamine–pyridine derivative, viz., a fluorescence probe was designed and synthesized. The probe displayed an “on–off–on” fluorescence switch, upon the sequential addition of Cu2+ and ethylenediaminetetraacetic acid (EDTA). The detection mechanism was confirmed by using UV-vis, fluorescence and 1H NMR titration spectra. Interestingly, the probe can accumulate in mitochondria, and thus detect Cu2+ in real-time there, which indicated that probe L can be used to monitor intracellular mitochondrial Cu2+ levels. Further understanding of the biological functions of Cu2+ in mitochondria has important implications for treating cancer and other diseases.
Co-reporter:Xiaoping Gan, Guangjin Liu, Mingjie Chu, Wengang Xi, Zili Ren, Xiuli Zhang, Yupeng Tian and Hongping Zhou
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 1) pp:NaN264-264
Publication Date(Web):2016/11/21
DOI:10.1039/C6OB02181F
Six D–π-A model compounds (compounds 1–6) were conveniently synthesized and characterized by 1H NMR, 13C NMR, MS and single crystal X-ray diffraction. One photon absorption and emission properties were studied by using a series of UV-visible and fluorescence spectra and theoretical calculations were applied to investigate the structure–property relationships, which showed that all six compounds possessed an obvious intramolecular charge transfer process which could be attributed to their optical properties. We simultaneously investigated their fluorescence emission performance in water/acetonitrile mixtures and found that they all have outstanding aggregation induced emission properties. Scanning electron microscopy testing illustrated that orderly aggregation was the main reason for their aggregation induced emission properties. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, and bio-imaging studies highlighted the potential application of the six compounds in one-photon fluorescence microscopy imaging domains.
Co-reporter:Xiaoping Gan, Guangjin Liu, Mingjie Chu, Wengang Xi, Zili Ren, Xiuli Zhang, Yupeng Tian and Hongping Zhou
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 9) pp:NaN2119-2119
Publication Date(Web):2017/02/08
DOI:10.1039/C7OB90023F
Correction for ‘Intermolecular interactions boost aggregation induced emission in carbazole Schiff base derivatives’ by Xiaoping Gan, et al., Org. Biomol. Chem., 2017, 15, 256–264.
Co-reporter:Zheng Zheng, Zhi-Peng Yu, Ming-Di Yang, Feng Jin, Li-Na Ye, Min Fang, Hong-Ping Zhou, Jie-Ying Wu and Yu-Peng Tian
Dalton Transactions 2014 - vol. 43(Issue 3) pp:NaN1150-1150
Publication Date(Web):2013/10/07
DOI:10.1039/C3DT52364K
By self-assembly of (E)-2-(3-(4-(1H-imidazol-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile (L1) and (E)-2-(3-(4-(1H-1,2,4-triazol-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile (L2) with silver(I) salts, eight new complexes, namely AgL12ClO4 (1), AgL12NO3 (2), [AgL12NO3]·C6H6 (3), [AgL12OOCCF3]·C6H6 (4), [AgL12PF6]·C6H6 (5), AgL22NO3 (6), [AgL2OOCCF3]2 (7) and AgL22PF6 (8), are presented along with an analysis of their structural features. The structures are built up through the combination of coordination bonds, Ag⋯π, Ag⋯F (or O), hydrogen bonding, and π⋯π stacking interactions to generate new supramolecular architectures. We observed the formation of two-dimensional coordination polymers for complex 7. Solvent benzene molecules and anions are dispersed in the supramolecular structure and play a vital role in building the supramolecular structures of the complexes. The nonlinear optical (NLO) properties of the complexes were investigated using the Z-scan technique and complexes 1, 2, 3, 4 and 7 show obviously nonlinear absorption compared with ligands (L1 and L2).
![2-Propenoic acid, 2-cyano-3-[4-(diphenylamino)phenyl]-, (2E)-](http://img.cochemist.com/ccimg/502700/502635-15-6.png)
![2-Propenoic acid, 2-cyano-3-[4-(diphenylamino)phenyl]-, (2E)-](http://img.cochemist.com/ccimg/502700/502635-15-6_b.png)
![N,N-BIS[2-(2-METHOXYETHOXY)ETHYL]ANILINE](http://img.cochemist.com/ccimg/484700/484679-02-9.png)
![N,N-BIS[2-(2-METHOXYETHOXY)ETHYL]ANILINE](http://img.cochemist.com/ccimg/484700/484679-02-9_b.png)
![Benzaldehyde, 3,4,5-tris[2-(2-methoxyethoxy)ethoxy]-](http://img.cochemist.com/ccimg/422300/422267-98-9.png)
![Benzaldehyde, 3,4,5-tris[2-(2-methoxyethoxy)ethoxy]-](http://img.cochemist.com/ccimg/422300/422267-98-9_b.png)
![Silane, [(2-isocyanophenyl)ethynyl]trimethyl-](http://img.cochemist.com/ccimg/213400/213334-93-1.png)
![Silane, [(2-isocyanophenyl)ethynyl]trimethyl-](http://img.cochemist.com/ccimg/213400/213334-93-1_b.png)
![Benzenamine, 4-[2-(4-nitrophenyl)ethenyl]-N,N-diphenyl-](http://img.cochemist.com/ccimg/142700/142677-07-4.png)
![Benzenamine, 4-[2-(4-nitrophenyl)ethenyl]-N,N-diphenyl-](http://img.cochemist.com/ccimg/142700/142677-07-4_b.png)
![Pyridinium,4-[2-[4-(dimethylamino)phenyl]ethenyl]-1-(3-sulfopropyl)-, inner salt](http://img.cochemist.com/ccimg/131100/131032-72-9.png)
![Pyridinium,4-[2-[4-(dimethylamino)phenyl]ethenyl]-1-(3-sulfopropyl)-, inner salt](http://img.cochemist.com/ccimg/131100/131032-72-9_b.png)
![Silane, [4-(4-methoxyphenyl)-1,3-butadiynyl]trimethyl-](http://img.cochemist.com/ccimg/130300/130248-54-3.png)
![Silane, [4-(4-methoxyphenyl)-1,3-butadiynyl]trimethyl-](http://img.cochemist.com/ccimg/130300/130248-54-3_b.png)
![Phosphonic acid, P-[[4-(diphenylamino)phenyl]methyl]-, diethyl ester](/data/chemimg/104500/126150-12-7.png)
![Phosphonic acid, P-[[4-(diphenylamino)phenyl]methyl]-, diethyl ester](/data/chemimg/104500/126150-12-7_b.png)
![Pyridinium, 4-[(1E)-2-[4-(dibutylamino)phenyl]ethenyl]-1-methyl-, iodide](http://img.cochemist.com/ccimg/97900/97807-64-2.png)
![Pyridinium, 4-[(1E)-2-[4-(dibutylamino)phenyl]ethenyl]-1-methyl-, iodide](http://img.cochemist.com/ccimg/97900/97807-64-2_b.png)
![N,n-dibutyl-4-[2-(1-methyl-4(1h)-pyridinylidene)ethylidene]-2,5-c Yclohexadien-1-iminium Iodide](http://img.cochemist.com/ccimg/95400/95378-72-6.png)
![N,n-dibutyl-4-[2-(1-methyl-4(1h)-pyridinylidene)ethylidene]-2,5-c Yclohexadien-1-iminium Iodide](http://img.cochemist.com/ccimg/95400/95378-72-6_b.png)
![[4-(DIETHYLAMINO)PHENYL]METHANOL](http://img.cochemist.com/ccimg/75000/74974-49-5.png)
![[4-(DIETHYLAMINO)PHENYL]METHANOL](http://img.cochemist.com/ccimg/75000/74974-49-5_b.png)
![{[5-(TRIFLUOROMETHYL)-2-PYRIDINYL]SULFONYL}ACETIC ACID](http://img.cochemist.com/ccimg/71200/71119-75-0.png)
![{[5-(TRIFLUOROMETHYL)-2-PYRIDINYL]SULFONYL}ACETIC ACID](http://img.cochemist.com/ccimg/71200/71119-75-0_b.png)
![Phosphonium, [[4-(2-benzoxazolyl)phenyl]methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/59600/59584-23-5.png)
![Phosphonium, [[4-(2-benzoxazolyl)phenyl]methyl]triphenyl-, bromide](http://img.cochemist.com/ccimg/59600/59584-23-5_b.png)
![2-[[4-(N-PHENYLANILINO)PHENYL]METHYLIDENE]PROPANEDINITRILE](http://img.cochemist.com/ccimg/40800/40703-88-6.png)
![2-[[4-(N-PHENYLANILINO)PHENYL]METHYLIDENE]PROPANEDINITRILE](http://img.cochemist.com/ccimg/40800/40703-88-6_b.png)
![4-(diethylamino)benzaldehyde [[4-(diethylamino)phenyl]methylene]hydrazone](http://img.cochemist.com/ccimg/29300/29228-93-1.png)
![4-(diethylamino)benzaldehyde [[4-(diethylamino)phenyl]methylene]hydrazone](http://img.cochemist.com/ccimg/29300/29228-93-1_b.png)
![Benzoxazole, 2-[4-(bromomethyl)phenyl]-](http://img.cochemist.com/ccimg/24300/24239-07-4.png)
![Benzoxazole, 2-[4-(bromomethyl)phenyl]-](http://img.cochemist.com/ccimg/24300/24239-07-4_b.png)
![Anthracene, 9-[2-(4-nitrophenyl)ethenyl]-](http://img.cochemist.com/ccimg/22300/22271-30-3.png)
![Anthracene, 9-[2-(4-nitrophenyl)ethenyl]-](http://img.cochemist.com/ccimg/22300/22271-30-3_b.png)
![1,4-Benzenediamine, N,N'-bis[[4-(dimethylamino)phenyl]methylene]-](http://img.cochemist.com/ccimg/15300/15257-27-9.png)
![1,4-Benzenediamine, N,N'-bis[[4-(dimethylamino)phenyl]methylene]-](http://img.cochemist.com/ccimg/15300/15257-27-9_b.png)
![1,4-Benzenediamine, N,N'-bis[[4-(diethylamino)phenyl]methylene]-](http://img.cochemist.com/ccimg/15300/15223-42-4.png)
![1,4-Benzenediamine, N,N'-bis[[4-(diethylamino)phenyl]methylene]-](http://img.cochemist.com/ccimg/15300/15223-42-4_b.png)
![Benzenamine, 4-[(1E)-2-(4-nitrophenyl)ethenyl]-N,N-diphenyl-](http://img.cochemist.com/ccimg/736200/736158-08-0.png)
![Benzenamine, 4-[(1E)-2-(4-nitrophenyl)ethenyl]-N,N-diphenyl-](http://img.cochemist.com/ccimg/736200/736158-08-0_b.png)
![Phosphonium, [[4-(diethylamino)phenyl]methyl]triphenyl-, iodide](http://img.cochemist.com/ccimg/526200/526196-98-5.png)
![Phosphonium, [[4-(diethylamino)phenyl]methyl]triphenyl-, iodide](http://img.cochemist.com/ccimg/526200/526196-98-5_b.png)
![2-CYANO-3-[4-(N-PHENYLANILINO)PHENYL]PROP-2-ENOIC ACID](http://img.cochemist.com/ccimg/30400/30388-31-9.png)
![2-CYANO-3-[4-(N-PHENYLANILINO)PHENYL]PROP-2-ENOIC ACID](http://img.cochemist.com/ccimg/30400/30388-31-9_b.png)
![Benzenamine, N,N-diphenyl-4-[2,2':6',2''-terpyridin]-4'-yl-](/data/chemimg/117200/408359-98-8.png)
![Benzenamine, N,N-diphenyl-4-[2,2':6',2''-terpyridin]-4'-yl-](/data/chemimg/117200/408359-98-8_b.png)
![4-(Benzo[d]oxazol-2-yl)aniline](http://img.cochemist.com/ccimg/21000/20934-81-0.png)
![4-(Benzo[d]oxazol-2-yl)aniline](http://img.cochemist.com/ccimg/21000/20934-81-0_b.png)
