Co-reporter:Ran Wang;Gang Li;Andong Zhang;Wen Wang;Guanwei Cui;Jianfeng Zhao;Bo Tang
Chemical Communications 2017 vol. 53(Issue 51) pp:6918-6921
Publication Date(Web):2017/06/22
DOI:10.1039/C7CC03682E
We design and synthesize four pyran-embedded perylene diimide (PDI) compounds through a straightforward methodology. UV-driven photocatalytic water splitting using the compounds as photocatalysts demonstrates that the highest photocatalytic H2 evolution rate under UV light is 0.90 mmol g−1 h−1, which paves the way towards organic photoresponsive materials.
Co-reporter:Yongshan Ma, Yunlong Zhao, Fengxia Zhang, Tianyi Jiang, Xiaofeng Wei, Han Shen, Ran Wang, Zhiqiang Shi
Sensors and Actuators B: Chemical 2017 Volume 241() pp:735-743
Publication Date(Web):31 March 2017
DOI:10.1016/j.snb.2016.10.148
•Two novel PTAC sensors containing chloroacetamides are synthesized and fully characterized.•The sensors can be utilized as colorimetric chemosensors for detection of F− ions in dichloromethane.•The F− sensitivity is introduced via the amide moiety (the NH proton in particular) upon either protonation or deprotonation.•There are obvious fluorescence color changes even detecting F− in solid state.Two novel fluorescence sensors (1 and 2) based on perylene tetra-(alkoxycarbonyl) derivative (PTAC) were designed and synthesized. The properties of sensors were detected by absorption, fluorescence spectra and electrochemical response. Test results indicated that the sensors had specific selectivity and high sensitivity for fluoride ion (F−) among the halide anions examined (F−, Cl−, Br− and I−). The absorption and fluorescence emission properties of the sensors arise from the intermolecular proton transfer (IPT) process between a hydrogen atom on the amide N position of sensor and the fluoride ion. Corresponding orbital electron distribution and molecular geometry configurations of the compounds were predicted by density functional theory (DFT). Moreover, sensor-based test strips can conveniently detect F− without any additional equipment. Incorporating S atom into perylene tetra esters 2 led to modified aromatic systems while retaining planarity and large conjugated π-bonds, and such molecular tailoring approach would be helpful for designing and synthesizing novel ratio metric fluorescent perylene chemosensors for F−.
Co-reporter:Yongshan Ma, Zhiqiang Shi, Andong Zhang, Jiaofu Li, Xiaofeng Wei, Tianyi Jiang, Yanan Li, Xiaolei Wang
Dyes and Pigments 2016 Volume 135() pp:41-48
Publication Date(Web):December 2016
DOI:10.1016/j.dyepig.2016.06.027
•A five-membered O-heterocyclic annulated perylene diimide (O-PDI) was synthesized.•Optical and electrical properties of O-PDI and S-PDI were investigated.•The self assembled nanostructures of O-PDI and S-PDI were investigated.•The geometric conformations and the packing arrangement of O-PDI and S-PDI were investigated.In this work, a new asymmetrically five-membered O-heterocyclic annulated perylene diimide (O-PDI) has been synthesized. The compounds O-PDI and asymmetrically five-membered S-heterocyclic annulated perylene diimide (S-PDI) self-assembled into nanoneedle and nanosheet, respectively. Photophysical, electrochemical and thermal properties were investigated by UV–vis absorption, fluorescence, cyclic voltammetric, thermogravimetric and differential scanning calorimetry techniques. Optical, fluorescence, scanning and transmission electron microscopies were employed in the molecular self-assembly studies. Due to significant electronic coupling between their heteroatom/heterocycles and perylene diimide (PDI) cores, the intermolecular π-π actions are neglectable, providing high luminescence efficiency. At the same time, the space between perylene chromophores is still very short (3.3 Å for O-PDI and 3.23 Å for S-PDI), which is favorable for the hopping transportation of charge carrier from one molecule to a neighboring one. These compounds could be candidate materials for acquiring well defined organic nanostructures with both excellent charge-transporting and good light-emitting capabilities.
Co-reporter:Yongshan Ma, Jiaofu Li, Shuguo Hou, Jinfeng Zhang, Zhiqiang Shi, Tianyi Jiang and Xiaofeng Wei
New Journal of Chemistry 2016 vol. 40(Issue 8) pp:6615-6622
Publication Date(Web):19 May 2016
DOI:10.1039/C6NJ00153J
A fluorescent pH-sensitive probe, 1-hydroxyl-3,4;9,10-tetra(n-butoxyloxycarbonyl)perylene (HPTBAC), was synthesized and used for pH sensing in living cells. The probe exhibits fluorescence emission characteristics with a pKa value of 7.9 and linear response to the very important pH range of 6.7–8.9. We designed a probe for binding the O− of hydroxyl in the perylene skeleton with H+ to possess the probing capability for detection in the acid to weak base pH range. The pH sensitivity is introduced via the O− moiety upon either protonation or deprotonation. In the deprotonation form, HPTBAC exhibits very weak emission due to strong electron-donating groups of O−. HPTBAC was successfully applied as a high-performance fluorochrome for living A549 cell (human lung cancer) and E. coli cell imaging. The results demonstrate that as a pH probe, HPTBAC is a good candidate for monitoring pH fluctuations in living cells.
Co-reporter:Liang Zhang, Ke Wang, Xuemin Qian, Huibiao Liu, and Zhiqiang Shi
ACS Applied Materials & Interfaces 2013 Volume 5(Issue 7) pp:2761
Publication Date(Web):March 12, 2013
DOI:10.1021/am4004914
Large area (26.7 cm2) nanotip arrays of porous conducting poly [5, 10, 15, 20-tetra (4-ethynylphenyl) porphyrin] diyne (TEPPD) have been successfully fabricated by an in situ cross-coupling reaction on the surface of the copper foil, which will open a new routine for large-area nanofabrication of porous conducting polymer on a conducting substrate. The surface-area of TEPPD nanotip arrays is up to 146 m2/ g. Interestingly, the nanotip arrays of TEPPD display a good field-emission property and exhibit a better stability of field emission than that of organic and polymeric nanostructures because of the good heat radiation of porous, which is comparable to some important nanostructures of inorganic semiconductor. The porous conducting polymer could be used for new field-emission emitter and other molecular electronic devices.Keywords: field emitter; large area; nanotip arrays; porous conjugated polymer;
Co-reporter:Rongzhou Wang, Zhiqiang Shi, Cuicui Zhang, Andong Zhang, Jiao Chen, Weiwei Guo, Zhaozhen Sun
Dyes and Pigments 2013 Volume 98(Issue 3) pp:450-458
Publication Date(Web):September 2013
DOI:10.1016/j.dyepig.2013.04.006
•3 typical asymmetrical intermediates of perylene monoimide diester were synthesized.•The bromination of 3 intermediates was investigated firstly.•Mono- and di-bromination were controlled by using different bromine concentration.•The bromination led to slight changes in absorption and obvious changes in emission.Dibutyl-perylene-3,4-anhydride-9,10-dicarbonylate (1) as an asymmetrical intermediate was synthesized in 80% yield by precipitation of the less soluble target molecule, which was formed through acidic hydrolysis of tetraesters of perylene tetracarboxylic acids at one side in a mixed solvent system. Based on the intermediate, two other asymmetrical intermediates 2 and 3 with monoimide group were also synthesized in high yields. The mono-bromination and di-bromination of 3 typical intermediates could be controlled by using different bromine concentration. The chemical structures of the brominated products and ratios of their isomers were confirmed directly or deduced from their phenol substituted products with MS and NMR spectra. The bromination of the intermediates mainly afforded isomers, but intermediates 1 and 2 could afford unique di-brominated product and mono-brominated product respectively. The bromination of the intermediates led to only slight changes in absorption spectra, but relatively obvious changes in emission spectra.
Co-reporter:Liang Zhang, Xuemin Qian, Libing Liu, Zhiqiang Shi, Yongjun Li, Shu Wang, Huibiao Liu and Yuliang Li
Chemical Communications 2012 vol. 48(Issue 49) pp:6166-6168
Publication Date(Web):02 May 2012
DOI:10.1039/C2CC32582A
Coordination polymers PZn quantum dots with a uniform diameter of 3 ± 0.5 nm were successfully prepared. The PZn QDs exhibit excellent water dispersibility, high photoluminescence, outstanding photostability and remarkable biocompatibility. The results of cellular experiments show that the PZn QDs are highly suitable for long-term cell imaging.
Co-reporter:Xiangxue Kong, Juan Gao, Tingting Ma, Ming Wang, Andong Zhang, Zhiqiang Shi, Yanhong Wei
Dyes and Pigments 2012 Volume 95(Issue 3) pp:450-454
Publication Date(Web):December 2012
DOI:10.1016/j.dyepig.2012.05.009
Mono-substituted perylene bisimides were synthesized in high yields under mild condition. The starting material was mono-nitrified perylene bisimides instead of usual perylene bisimides halogenated at different levels. Besides phenols and amine, the nucleophilic reagents included alcohol and thiol. The substitution of nitro group was easier and more effective than the substitution of halogen atoms. But the substitution reaction of pyrrolidine afforded mono- and 1,6-disubstituted perylene bisimides owing to the high activity of nitrified perylene bisimides and pyrrolidine. Several replacement reactions between phenols and alcohol based on phenol mono-substituted perylene bisimide were also found. The replacement reactions between phenols was fast and in high yield. The absorption of the mono-substituted perylene bisimides were tunable in the whole visible region.Graphical abstractHighlights► Substitution reactions of mono-nitrified perylene bisimides were investigated. ► Substitution groups including phenols, alcohol, thioalcohol and amine. ► Substitution reactions carried out at room temperature or fluxed chloroform. ► Replacement reactions of mono-phenol substituted PBIs were found.
Co-reporter:Juan Gao, Dan He, Wei Zhang, Zuo Xiao, Qiqun Zuo, Zhiqiang Shi, Liming Ding
Synthetic Metals 2012 Volume 162(17–18) pp:1694-1700
Publication Date(Web):October 2012
DOI:10.1016/j.synthmet.2012.07.001
A new acceptor unit, 2-alkyl-thieno[3,4-b]imidazole, was synthesized through an annulation reaction between a 3,4-diaminothiophene derivative and a carboxyl acid or an acyl chloride, and was used for developing donor–acceptor conjugated copolymers. Copolymerization of 2-alkyl-thieno[3,4-b]imidazole and benzo[1,2-b:3,4-b′]dithiophene (BDT) or dithieno[3,2-b:2′,3′-d]silole (DTS) afforded 6 new low bandgap polymers P1–P6. These polymers possess intensive absorption at 400–650 nm and the optical bandgaps are in the range of 1.69–1.88 eV. They were firstly applied in polymer solar cells and the best efficiency of 0.72% was obtained from P2/PC71BM cells fabricated using a dip-coating method.Graphical abstractHighlights► A new acceptor unit, 2-alkyl-thieno[3,4-b]imidazole, was synthesized through an annulation reaction. ► Six new low bandgap polymers were developed based on 2-alkyl-thieno[3,4-b]imidazole. ► Polymer solar cells were fabricated using a dip-coating method and 0.72% PCE was achieved.
Co-reporter:Ping Xu;Cuicui Pan;Yingjie Zhao;Xiangxue Kong;Juanjuan Sun;Maoyou Xu
Luminescence 2012 Volume 27( Issue 4) pp:307-309
Publication Date(Web):
DOI:10.1002/bio.1355
ABSTRACT
A novel fluorescent pH sensor with tunable response range was designed based on highly fluorescent 3,4:9,10-perylene tetracarboxylic ammonium, which could coordinate the paramagnetic Fe3+ ions to turn off its fluorescence and could also release Fe3+ to turn on the fluorescence again at higher pH. The fluorescent pH sensor was tunable in the presence of different ligands in aqueous solution. Copyright © 2011 John Wiley & Sons, Ltd.
Co-reporter:Chengfen Xing;Libing Liu;Yuliang Li;Shu Wang
Advanced Functional Materials 2010 Volume 20( Issue 13) pp:2175-2180
Publication Date(Web):
DOI:10.1002/adfm.200902155
Abstract
A new water-soluble zwitterionic oligofluorene bearing carboxylic acid and quaternary ammonium as pendant groups (OF-1) is synthesized and characterized. It forms aggregates by intermolecular electrostatic interactions and exhibits similar light-harvesting ability as that of conjugated polymers. Efficient fluorescence resonance energy transfer (FRET) occurs from OF-1 to double-stranded DNA tagged with fluorescein (dsDNA-F1). A photoresponsive oligofluorene (OF-3) is also synthesized by protecting OF-1 with 1-(2-nitrophenyl)ethanol. Photolysis of OF-3 can produce OF-1 to result in a fluorescence “turn-on” response, thus the FRET from OF-3 to dsDNA-Fl can be turned on by light irradiation. OF-3 offers the potential for remote DNA sensing.
Co-reporter:Xue Wu, Chuanwei Yin, Zhiqiang Shi, Maoyou Xu, Jin Zhang and Juanjuan Sun
New Journal of Chemistry 2010 vol. 34(Issue 1) pp:61-64
Publication Date(Web):23 Oct 2009
DOI:10.1039/B9NJ00364A
A novel substitution reaction of perylene bisimides has been developed. The Ph2PO group was attached to the PBI core at the α-position instead of the usual bay position. This substitution kept the high fluorescence of the PBI dyes and caused the adjacent proton at the bay position and a tertiary proton at the cyclohexyl group to be shifted significantly in the 1H-NMR spectra.
Co-reporter:Yingjie Zhao;Xin Zhang;Dianqing Li;Daicheng Liu;Wenfeng Jiang;Cixiang Han
Luminescence 2009 Volume 24( Issue 3) pp:140-143
Publication Date(Web):
DOI:10.1002/bio.1078
Abstract
Highly water-soluble 3,4:9,10-perylene tetracarboxylic ammonium with quantitative fluorescence quantum yield was designed. Owing to the high negative electrostatic potential of the perylene plane, the perylene dye remained stable over a broad pH range and was successfully applied as a high-performance fluorochrome for living hippocampal neurons staining. Copyright © 2009 John Wiley & Sons, Ltd.
Co-reporter:Wenfeng Jiang, Ying Yu, Dianqing Li, Yingjie Zhao, Maoyou Xu and Zhiqiang Shi
New Journal of Chemistry 2008 vol. 32(Issue 4) pp:581-583
Publication Date(Web):28 Feb 2008
DOI:10.1039/B719900G
Core–shell nanospheres, titania composite nanospheres containing [60]fullerene, were fabricated with sizes of about 100 nm by a layer-by-layer self-assembly procedure, and were characterized by TGA, FT-IR and XPS spectroscopy.
Co-reporter:Minghui Yu;Yuliang Li;Daoben Zhu;Chengfen Xing;Shu Wang
Macromolecular Rapid Communications 2007 Volume 28(Issue 3) pp:241-245
Publication Date(Web):30 JAN 2007
DOI:10.1002/marc.200600744
A fluorescent turn-on detection for nitric oxide in aqueous solution is developed using cationic conjugated polymers. The assay benefits from the sensitivity of optical signals from conjugated polymers and the simplicity of fluorescence measurement techniques. The assay contains three elements: a cationic conjugated polymer that contains imidazole moieties, Cu2+ ions, and the target nitric oxide. The highly fluorescent conjugated polymer coordinates to Cu2+ ions through weak N · · · Cu interactions, and its fluorescence is efficiently quenched by a photo-induced electron transfer process (‘off’ state). In the presence of nitric oxide, the transformation of the paramagnetic Cu2+ ion into a diamagnetic Cu1+ ion inhibits the quenching and, therefore, the fluorescence of the conjugate polymer is recovered (‘on’ state). Other biologically relevant reactive nitrogen species, such as NOBF4, NaNO2, and NaNO3 don't exhibit the fluorescence recovery of the conjugated polymer under the same conditions as nitric oxide. The cationic conjugated polymer/Cu2+ complex can thus be used as a platform to detect nitric oxide in aqueous solution with high sensitivity and selectivity.
Co-reporter:Ying Yu, Jun-sen Wu, Yong-shan Ma, Chen-hui Wang and Zhi-qiang Shi
New Journal of Chemistry 2006 vol. 30(Issue 1) pp:18-21
Publication Date(Web):28 Nov 2005
DOI:10.1039/B513266E
The core–shell nanospheres fullerenol–TiO2 and C60@2β-CD–TiO2 were fabricated by a layer-by-layer self-assembly procedure seeding with fullerenols and C60@2β-CD respectively, the nanospheres ranging in size from 40 to 80 nm and 10–20 nm in diameter respectively. The presence of fullerenols in the nanostructures was confirmed by XPS and FT-IR spectroscopy, and the XRD patterns prove both the titania shells on fullerenol and C60@2β-CD are rutile and anatase phases.
Co-reporter:Liang Zhang, Xuemin Qian, Libing Liu, Zhiqiang Shi, Yongjun Li, Shu Wang, Huibiao Liu and Yuliang Li
Chemical Communications 2012 - vol. 48(Issue 49) pp:NaN6168-6168
Publication Date(Web):2012/05/02
DOI:10.1039/C2CC32582A
Coordination polymers PZn quantum dots with a uniform diameter of 3 ± 0.5 nm were successfully prepared. The PZn QDs exhibit excellent water dispersibility, high photoluminescence, outstanding photostability and remarkable biocompatibility. The results of cellular experiments show that the PZn QDs are highly suitable for long-term cell imaging.
Co-reporter:Ran Wang, Gang Li, Andong Zhang, Wen Wang, Guanwei Cui, Jianfeng Zhao, Zhiqiang Shi and Bo Tang
Chemical Communications 2017 - vol. 53(Issue 51) pp:NaN6921-6921
Publication Date(Web):2017/06/05
DOI:10.1039/C7CC03682E
We design and synthesize four pyran-embedded perylene diimide (PDI) compounds through a straightforward methodology. UV-driven photocatalytic water splitting using the compounds as photocatalysts demonstrates that the highest photocatalytic H2 evolution rate under UV light is 0.90 mmol g−1 h−1, which paves the way towards organic photoresponsive materials.
