Co-reporter:Jie Zhang, Wenjie Wang, Yong Liu, Jing Zhi Sun, Anjun Qin, and Ben Zhong Tang
Macromolecules November 14, 2017 Volume 50(Issue 21) pp:8554-8554
Publication Date(Web):October 18, 2017
DOI:10.1021/acs.macromol.7b01592
Water is an abundant, natural, and sustainable resource. However, it has not been used as a monomer for the construction of polymers. In this paper, we take this challenge and develop a new polymerization of water and triple-bond based monomers of isocyanides and bromoalkynes, and polyamides with high molecular weights (up to 41 700) and stereoregularities (the fraction of Z-isomer generally higher than 80%) are obtained in excellent yields (up to 98.1%) under mild reaction conditions. The polymers possess good solubility and exhibit high thermal stability and refractive index. The tetraphenylethene-containing polymers show the unique aggregation-enhanced emission (AEE) characteristics. Moreover, thanks to their containing bromoacrylamide groups in the main chains, these polyamides could be easily postmodified through different reactions, providing a convenient platform for polymer functionalization. Thus, this work not only established a stereoselective polymerization of water and triple-bond based monomers but also provided a powerful strategy for the preparation of functional polyamides under mild reaction conditions.
Co-reporter:Lingzhi Li;Han Nie;Ming Chen;Jingzhi Sun;Ben Zhong Tang
Faraday Discussions 2017 (Volume 196) pp:245-253
Publication Date(Web):2017/02/20
DOI:10.1039/C6FD00163G
A tetraphenylbenzene (TPB) cored luminophore of TPB-AC with aggregation-enhanced emission characteristics was designed and synthesized. TPB-AC could be potentially applied for the fabrication of high performance organic light-emitting diodes (OLEDs) with blue light emission.
Co-reporter:
Journal of Polymer Science Part A: Polymer Chemistry 2017 Volume 55(Issue 4) pp:616-621
Publication Date(Web):2017/02/15
DOI:10.1002/pola.28419
ABSTRACTAs an emerged efficient polymerization methodology, the click polymerization plays a significant role in the area of polymer and materials sciences. Similar to the click reaction, the click polymerization enjoys the advantages of high efficiency, mild reaction conditions, and high regio- and stereo-selectivity etc. In this highlight, we summarize the recent progress on click polymerizations, with focus on the alkyne-based ones. The challenges and opportunities in this area are also briefly discussed. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 616–621
Co-reporter:Yang Shi;Yuanjing Cai;Yi Jia Wang;Ming Chen;Han Nie;Wei Qin
Science China Chemistry 2017 Volume 60( Issue 5) pp:635-641
Publication Date(Web):02 March 2017
DOI:10.1007/s11426-016-0433-x
The luminogens with aggregation-induced emission (AIEgens) characteristics have been widely applied in diverse areas. However, the n-type AIEgens are to be further developed. In this paper, we designed and synthesized an n-type multifunctional AIEgen of tetraphenylethene-substituted 3,4,5-triphenyl-4H-1,2,4-triazole (BTPE-TAZ). This AIEgen can serve as both light-emitting and electron-transporting layers in organic light-emitting devices. Moreover, it also exhibits the interesting optical waveguide and reversible mechanochromic luminescence properties, which are of great potential for practical applications.
Co-reporter:Ming Chen, Han Nie, Bo Song, Lingzhi Li, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Journal of Materials Chemistry A 2016 vol. 4(Issue 14) pp:2901-2908
Publication Date(Web):18 Nov 2015
DOI:10.1039/C5TC03299G
Aggregation-induced emission (AIE) is a unique photo-physical phenomenon and has become an emerging and hot research area. With the enthusiastic efforts paid by researchers, hundreds of AIE-active luminogens (AIEgens) have been generated but heterocyclic AIEgens are rarely reported. Recently, we enriched the family of AIEgens and reported a pyrazine-based AIEgen of tetraphenylpyrazine (TPP), which could be facilely functionalized by a post-synthetic strategy. In this work, we further expanded the TPP-based AIE system by covalently attaching one, two or four electron-donating triphenylamine moieties to the TPP core via Suzuki coupling, and TPP–TPA, TPP–2TPA and TPP–4TPA were produced, respectively. Thanks to their donor-π-acceptor structures, these luminogens exhibit multi-functional properties, such as excellent thermal stability (up to 504 °C), large molar absorptivity, bright emission in the solid state (quantum yields up to 35.2%), solvatochromism, and high two-photon absorption cross-sections (up to 480 GM). Furthermore, using TPP–TPA as the emitting layer, a triple-layer device was fabricated and a turn-on voltage, maximum luminance, current efficiency, power efficiency, and external quantum efficiency of 3.7 V, 17459 cd m−2, 5.49 cd A−1, 3.18 lm W−1 and 2.88% were realized, respectively. These results indicate a huge potential to develop high-tech applications based on these TPP-based AIEgens.
Co-reporter:Ming Chen, Lingzhi Li, Han Nie, Jiaqi Tong, Lulin Yan, Bin Xu, Jing Zhi Sun, Wenjing Tian, Zujin Zhao, Anjun Qin and Ben Zhong Tang
Chemical Science 2015 vol. 6(Issue 3) pp:1932-1937
Publication Date(Web):11 Dec 2014
DOI:10.1039/C4SC03365E
Research on aggregation-induced emission (AIE) has been a hot topic. Due to enthusiastic efforts by many researchers, hundreds of AIE luminogens (AIEgens) have been generated which were mainly based on archetypal silole, tetraphenylethene, distyrylanthracene, triphenylethene, and tetraphenyl-1,4-butadiene, etc. To enlarge the family of AIEgens and to enrich their functions, new AIEgens are in high demand. In this work, we report a new kind of AIEgen based on tetraphenylpyrazine (TPP), which could be readily prepared under mild reaction conditions. Furthermore, we show that the TPP derivatives possess a good thermal stability and their emission could be fine-tuned by varying the substituents on their phenyl rings. It is anticipated that TPP derivatives could serve as a new type of widely utilized AIEgen, based on their facile preparation, good thermo-, photo- and chemostabilities, and efficient emission.
Co-reporter:Haoke Zhang, Hongkun Li, Jia Wang, Jingzhi Sun, Anjun Qin and Ben Zhong Tang
Journal of Materials Chemistry A 2015 vol. 3(Issue 20) pp:5162-5166
Publication Date(Web):10 Apr 2015
DOI:10.1039/C5TC00629E
Axial chiral aggregation-induced emission (AIE) luminogens of (R)-3,3′-BTPE-BINA, (R)-6,6′-BTPE-BINA and (S)-6,6′-BTPE-BINA were synthesized for the first time by covalently attaching the AIE-active tetraphenylethene (TPE) units to the axial chiral binaphthol (BINOL) moieties at their 3,3′- or 6,6′-positions. It was found that the circular dichroism (CD) value when TPE was attached to BINOL at its 3,3′-positions was much larger than that found after its attachment at 6,6′-positions. The resultant AIE-active luminogens (AIEgens) show high quantum yields (up to 42.4%) in their aggregated states. Interestingly, these AIEgens exhibit an abnormal aggregation-annihilation CD (AACD) phenomenon. The decrease in the twisted angle between the two naphthalene rings upon aggregation was rationalized as the cause of this unique effect.
Co-reporter:Ming Chen, Lingzhi Li, Han Nie, Yang Shi, Ju Mei, Jian Wang, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2015 vol. 51(Issue 53) pp:10710-10713
Publication Date(Web):20 May 2015
DOI:10.1039/C5CC03181H
N-type pyrazine-based 1,4- and 1,5-disubstituted 1,2,3-triazole derivatives, showing unique aggregation-enhanced emission characteristics, were facilely prepared via Cu- and Ru-catalysed azide–alkyne cycloadditions, respectively. Thanks to their electron-deficient properties, they could readily form red-emissive charge transfer complexes with electron-donating triphenylamine in the aggregate and solid states.
Co-reporter:Lingzhi Li, Ming Chen, Haoke Zhang, Han Nie, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2015 vol. 51(Issue 23) pp:4830-4833
Publication Date(Web):04 Feb 2015
DOI:10.1039/C5CC00241A
The influence of the number and substitution position of phenyl groups on the aggregation-enhanced emission of benzene-cored luminogens is unambiguously revealed.
Co-reporter:Bicheng Yao;Jing Zhi Sun
Journal of Inorganic and Organometallic Polymers and Materials 2015 Volume 25( Issue 1) pp:37-46
Publication Date(Web):2015 January
DOI:10.1007/s10904-014-0106-0
Ferrocene-containing polymers (FcPs) have attracted much research interest in the last decade, due to their unique properties and enormous applications. However, it is a great synthetic challenge to prepare FcPs before the advent of click chemistry. In this review, we summarized the recent research efforts on synthesizing FcPs through click reactions, which include click modification of preformed polymers and click polymerization of ferrocene (Fc) containing monomers. Due to the containing Fc moieties, the FcPs enjoy excellent redox activity, thermal stability, electrochemical property, and magnetism. Accordingly, they are promising to be used as electrochemical sensors, catalysts, magneto-ceramics, electrode modifiers, optical devices, etc.
Co-reporter:Haiqiang Wu;Wenhui Dong;Zongtan Wang;Bicheng Yao;Ming Chen
Science China Chemistry 2015 Volume 58( Issue 11) pp:1748-1752
Publication Date(Web):2015 November
DOI:10.1007/s11426-015-5475-x
An air-stable supported Cu(I) catalyst, CuI@PS-Phen, was designed and synthesized. CuI@PS-Phen can efficiently catalyze the click polymerization of diynes a and diazides b to produce soluble and thermally stable polytriazoles with high molecular weights (Mw up to 30800), and low copper residue content (down to 190 ppm) in high yields (up to 94.2%) under mild reaction conditions without the exclusion of oxygen.
Co-reporter:Bicheng Yao, Ting Hu, Haoke Zhang, Jie Li, Jing Zhi Sun, Anjun Qin, and Ben Zhong Tang
Macromolecules 2015 Volume 48(Issue 21) pp:7782-7791
Publication Date(Web):October 27, 2015
DOI:10.1021/acs.macromol.5b01868
Multifunctional hyperbranched polymers have found wide applications in diverse areas. However, the preparation of these polymers is generally under harsh polymerization conditions with limited reactions. In this work, we prepared multifunctional hyperbranched poly(vinylene sulfide)s (hb-PVSs) by our established efficient and spontaneous thiol–yne click polymerization for the first time. A series of hb-PVSs with high molecular weights (Mw up to 63100) were obtained in high yields (up to 86%) from the polymerizations of monomers 1 and 2 with equivalent molar ratio in THF at 20 °C for 2 h. All the hb-PVSs are regioregular, soluble, and thermally stable. Thanks to the unreacted ethynyl groups on their peripheries, the hb-PVSs could be facilely functionalized by consecutive thiol–yne click reactions. Moreover, the solid films of hb-PVSs exhibit higher refractive index (RI) values (n > 1.64) than those of traditional optical plastics. The TPE-containing hb-PVS shows unique aggregation-enhanced emission characteristic and its aggregates could be used to detect explosives with superamplification effect. Therefore, this work not only proves the universality of our developed spontaneous thiol–yne click polymerization but also provides a powerful and versatile platform for the preparation of multifunctional sulfur-containing polymers.
Co-reporter:Yunbo Cai, Lingzhi Li, Zongtan Wang, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2014 vol. 50(Issue 64) pp:8892-8895
Publication Date(Web):16 Jun 2014
DOI:10.1039/C4CC02844A
A novel tetraphenylethene-based fluorescent H2S probe was designed and synthesized, which exhibited high selectivity and tuneable sensitivity, making direct indication of H2S concentration in blood and unknown samples possible.
Co-reporter:Zhe Wang, Yang Shi, Jian Wang, Lingzhi Li, Haiqiang Wu, Bicheng Yao, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Polymer Chemistry 2014 vol. 5(Issue 20) pp:5890-5894
Publication Date(Web):15 Jul 2014
DOI:10.1039/C4PY00859F
The first example of InCl3-catalyzed polycyclotrimerization of diynes to generate regioregular hyperbranched polymers was developed. The InCl3/2-iodophenol-catalyzed polycyclotrimerization of aromatic/aliphatic diynes in chlorobenzene readily furnished soluble 1,3,5-trisubstituted benzene-cored hyperbranched polyarylenes with high weight-averaged molecular weights (up to 37200) in high yields (up to 87.8%). Thanks to its low cost and moisture-tolerance, this catalytic system is promising to be widely applied in preparation of regioregular functional hyperbranched polymers with unique properties.
Co-reporter:Engui Zhao, Hongkun Li, Jun Ling, Haiqiang Wu, Jian Wang, Shuang Zhang, Jacky W. Y. Lam, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Polymer Chemistry 2014 vol. 5(Issue 7) pp:2301-2308
Publication Date(Web):27 Nov 2013
DOI:10.1039/C3PY01387A
Aggregation-induced emission (AIE) and aggregation-enhanced emission (AEE) have recently been a hot research topic. Currently, efforts have been mostly made on low mass molecules. Their structure–property relationship has been well-established but no work on polymers has been reported, probably due to the harsh reaction conditions for most of the polymerization processes. We used the powerful and facile Cu(I)-catalysed click polymerization in this paper to synthesize four polytriazoles with small variation in either the backbones or the linking manner of the triazole. The results show that changing the hydrogen groups of the stilbene units of P3b and P6b to the phenyl rings of the tetraphenylethene moieties of P3a and P6a readily leads to distinctive differences in their photophysical properties. P3a and P6a are AEE-active, while P3b and P6b display a typical aggregation-caused quenching effect. Meanwhile, investigation on the linking manner of 1,4-positions of the triazole ring indicates that this variation exerts little influence on the emission properties. This work could thus serve as a guideline for the further design of luminogenic polymers for high-tech applications.
Co-reporter:Hongkun Li;Zhe Wang;Jie Li;Engui Zhao;Jing Zhi Sun;Jacky W. Y. Lam;Ben Zhong Tang
Macromolecular Chemistry and Physics 2014 Volume 215( Issue 10) pp:1036-1041
Publication Date(Web):
DOI:10.1002/macp.201400108
Co-reporter:Junwei Li;Yuan Li;Dr. Carrie Y. K. Chan;Dr. Ryan T. K. Kwok;Dr. Hongkun Li;Pavel Zrazhevskiy; Xiaohu Gao; Jing Zhi Sun; Anjun Qin; Ben Zhong Tang
Angewandte Chemie 2014 Volume 126( Issue 49) pp:13736-13740
Publication Date(Web):
DOI:10.1002/ange.201408757
Abstract
An in-depth understanding of dynamic interfacial self-assembly processes is essential for a wide range of topics in theoretical physics, materials design, and biomedical research. However, direct monitoring of such processes is hampered by the poor imaging contrast of a thin interfacial layer. We report in situ imaging technology capable of selectively highlighting self-assembly at the phase boundary in real time by employing the unique photophysical properties of aggregation-induced emission. Its application to the study of breath-figure formation, an immensely useful yet poorly understood phenomenon, provided a mechanistic model supported by direct visualization of all main steps and fully corroborated by simulation and theoretical analysis. This platform is expected to advance the understanding of the dynamic phase-transition phenomena, offer insights into interfacial biological processes, and guide development of novel self-assembly technologies.
Co-reporter:Bicheng Yao, Ju Mei, Jie Li, Jian Wang, Haiqiang Wu, Jing Zhi Sun, Anjun Qin, and Ben Zhong Tang
Macromolecules 2014 Volume 47(Issue 4) pp:1325-1333
Publication Date(Web):February 5, 2014
DOI:10.1021/ma402559a
The “thio-click” polymerization is a well-expanded concept of click polymerization. Among the click polymerizations, the thiol–yne click polymerization is less developed and still in its infancy stage. In general, UV light, elevated temperature, amine, or transition metal complexes is needed to catalyze the thiol–yne click polymerization, which greatly complicates the experimental operation and limits its application. In this work, a facile and powerful thiol–yne click polymerization was developed, which could be carried out under very mild conditions without using external catalyst. Simply mixing the aromatic diynes (1a–1e) and dithiols (2–4) with equivalent molar ratio in THF at 30 °C will readily produce soluble and regioregular functional poly(vinylene sulfide)s (PIa–PIe, PII, and PIII) with high molecular weights (Mw up to 85 200) in excellent yields (up to 97%) after as short as 2 h. Furthermore, no double addition product of an ethynyl group was found. This catalyst-free thiol–yne click polymerization has remarkably simplified the reaction conditions and will facilitate the preparation of functional materials applied in diverse areas.
Co-reporter:Junwei Li;Yuan Li;Dr. Carrie Y. K. Chan;Dr. Ryan T. K. Kwok;Dr. Hongkun Li;Pavel Zrazhevskiy; Xiaohu Gao; Jing Zhi Sun; Anjun Qin; Ben Zhong Tang
Angewandte Chemie International Edition 2014 Volume 53( Issue 49) pp:13518-13522
Publication Date(Web):
DOI:10.1002/anie.201408757
Abstract
An in-depth understanding of dynamic interfacial self-assembly processes is essential for a wide range of topics in theoretical physics, materials design, and biomedical research. However, direct monitoring of such processes is hampered by the poor imaging contrast of a thin interfacial layer. We report in situ imaging technology capable of selectively highlighting self-assembly at the phase boundary in real time by employing the unique photophysical properties of aggregation-induced emission. Its application to the study of breath-figure formation, an immensely useful yet poorly understood phenomenon, provided a mechanistic model supported by direct visualization of all main steps and fully corroborated by simulation and theoretical analysis. This platform is expected to advance the understanding of the dynamic phase-transition phenomena, offer insights into interfacial biological processes, and guide development of novel self-assembly technologies.
Co-reporter:Hongkun Li, Lingzhi Li, Haiqiang Wu, Jacky W. Y. Lam, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Polymer Chemistry 2013 vol. 4(Issue 22) pp:5537-5541
Publication Date(Web):31 Jul 2013
DOI:10.1039/C3PY00892D
Ferrocene-based poly(aroxycarbonyltriazole)s with high molecular weights and regioregularities were prepared in high yields by the efficient metal-free click polymerization of dipropiolates and the ferrocene-containing diazide under mild reaction conditions. The resulting polytriazoles are redox active, and could be used as precursors to generate soft magnetic ceramics with high magnetizability and low coercivity when pyrolyzed at elevated temperatures.
Co-reporter:Qiang Wang, Hongkun Li, Qiang Wei, Jing Zhi Sun, Jian Wang, Xiao A. Zhang, Anjun Qin and Ben Zhong Tang
Polymer Chemistry 2013 vol. 4(Issue 5) pp:1396-1401
Publication Date(Web):01 Nov 2012
DOI:10.1039/C2PY20797D
The Cu(I)-catalyzed azide–alkyne click polymerization has become a powerful tool for the preparation of functional polytriazoles. However, copper residues in the products could harm the performance of optoelectronic devices and be cytotoxic in biological applications. The complete removal of these residues after reaction from the polymers is therefore necessary but difficult. The metal-free azide–alkyne click polymerization (MFCP) provides a solution to this problem. Currently, the MFCP is facilitated by activated alkynes, and no activated comonomer, i.e. azide, has been reported. In this paper, an activated azide, 4,4′-diazidoperfluorobenzophenone, was designed and synthesized. Compared to the ordinary azide, such a monomer can remarkably accelerate the MFCP with alkynes. Thus, a new MFCP of activated azide and alkyne was established, and polytriazoles with high regioregularity (fraction of 1,4-isomer higher than 82%) and satisfactory molecular weights (Mw up to 34000) were produced in high yields (up to 95.1%).
Co-reporter:Qiang Wang;Ming Chen;Bicheng Yao;Jian Wang;Ju Mei;Jing Zhi Sun;Ben Zhong Tang
Macromolecular Rapid Communications 2013 Volume 34( Issue 9) pp:796-802
Publication Date(Web):
DOI:10.1002/marc.201200838
Co-reporter:Hongkun Li, Haiqiang Wu, Engui Zhao, Jie Li, Jing Zhi Sun, Anjun Qin, and Ben Zhong Tang
Macromolecules 2013 Volume 46(Issue 10) pp:3907-3914
Publication Date(Web):May 16, 2013
DOI:10.1021/ma400609m
The metal-free click polymerization (MFCP) of azide and alkyne has become a powerful tool for the synthesis of functional polytriazoles. Among which, the MFCP of propiolate and azide has been used to prepare functional linear poly(aroxycarbonyltriazole)s (PACTs). Their hyperbranched analogues, however, have been rarely prepared. In this paper, hyperbranched PACTs with satisfactory molecular weights and high regioregularities were synthesized in high yields by the MFCP of tripropiolates (1) and tetraphenylethene (TPE)-containing diazide (2) under the optimized reaction conditions without protection from oxygen and moisture. The resultant polymers are soluble in common organic solvents and thermally stable, with 5% loss of their weights at temperatures higher than 330 °C. The polymers exhibit high refractive indices with low chromatic dispersion. Thanks to their contained TPE units, the polymers show the unique feature of aggregation-induced emission, and their aggregates can function as fluorescent sensors for the detection of explosives with the superamplification quenching effect. Furthermore, the polymers can be readily photo-cross-linked, yielding two-dimensional fluorescent patterns with high resolution.
Co-reporter:BiCheng Yao;JingZhi Sun;Ben Zhong Tang
Science Bulletin 2013 Volume 58( Issue 22) pp:2711-2718
Publication Date(Web):2013 August
DOI:10.1007/s11434-013-5892-1
The research on using thiol-ene click reaction to synthesize sulfur-containing polymers with topological structures and advanced functional properties is a hot topic. However, the application of the thiol-yne reaction in the functional polymer preparation is limited and the thiol-yne click polymerization is to be further developed. In this review, we summarized recent research efforts on using thiol-yne click polymerization to synthesize polymers with topological structures. The sulfur-containing polymers were facilely prepared by photo- and thermo-initiated, amine-mediated, and transition-metal-catalyzed thiol-yne click polymerizations. These polymers are promising to be used as drug-delivery vehicles, high refractive index optical materials, photovoltaic materials, and biomaterials etc.
Co-reporter:ZongTan Wang;Yuan Fang;JingZhi Sun;Ben Zhong Tang
Science China Chemistry 2013 Volume 56( Issue 9) pp:1187-1190
Publication Date(Web):2013 September
DOI:10.1007/s11426-013-4933-6
The research on aggregation-induced emission (AIE) has drawn increasing interests in the past decade. With the efforts scientists paid, a variety of AIE systems have been developed, among which the tetraphenylethelene and silole derivatives are the most studied. Development of new AIE systems could further enrich the AIE molecules and promote the development of AIE area. In this communication, we prepared a new AIE system based on 1,2,4,6-tetraphenylpyridinium ions according to the restriction of intramolecular rotation mechanism. These molecules could be facilely synthesized via one-step and one-pot reaction. The ionic AIE-active molecules could find wide application in sensing and optoelectronic areas.
Co-reporter:Jian Wang ; Ju Mei ; Rongrong Hu ; Jing Zhi Sun ; Anjun Qin ;Ben Zhong Tang
Journal of the American Chemical Society 2012 Volume 134(Issue 24) pp:9956-9966
Publication Date(Web):May 18, 2012
DOI:10.1021/ja208883h
It has been difficult to decipher the mechanistic issue whether E/Z isomerization is involved in the aggregation-induced emission (AIE) process of a tetraphenylethene (TPE) derivative, due to the difficulty in the synthesis of its pure E and Z conformers. In this work, pure stereoisomers of a TPE derivative named 1,2-bis{4-[1-(6-phenoxyhexyl)-4-(1,2,3-triazol)yl]phenyl}-1,2-diphenylethene (BPHTATPE) are successfully synthesized. Both isomers show remarkable AIE effect (αAIE ≥ 322) and high fluorescence quantum yield in the solid state (ΦF 100%). The conformers readily undergo E/Z isomerization upon exposure to a powerful UV light and treatment at a high temperature (>200 °C). Such conformational change, however, is not observed under normal fluorescence spectrum measurement conditions, excluding the involvement of the E/Z isomerization in the AIE process of the TPE-based luminogen. The molecules of (E)-BPHTATPE self-organize into ordered one-dimensional nanostructures such as microfibers and nanorods that show obvious optical waveguide effect. BPHTATPE shows rich chromic effects, including mechano-, piezo-, thermo-, vapo-, and chronochromisms. Its emission peak is bathochromically shifted by simple grinding and pressurization and the spectral change is reversed by fuming with a polar solvent, heating at a high temperature, or storing at room temperature for some time. The multiple chromic processes are all associated with changes in the modes of molecular packing.
Co-reporter:Ju Mei, Jian Wang, Jing Zhi Sun, Hui Zhao, Wangzhang Yuan, Chunmei Deng, Shuming Chen, Herman H. Y. Sung, Ping Lu, Anjun Qin, Hoi Sing Kwok, Yuguang Ma, Ian D. Williams and Ben Zhong Tang
Chemical Science 2012 vol. 3(Issue 2) pp:549-558
Publication Date(Web):25 Oct 2011
DOI:10.1039/C1SC00688F
Three dimethyltetraphenylsiloles (DMTPSs) symmetrically substituted on their 2,5-positions with electron-accepting (A), i.e.aldehyde (ALD) and dicyanovinyl (DCV) or donating (D), i.e.diphenylamine (DPA) moieties were designed and synthesized via facile reaction procedures. The propeller-shaped luminogens exhibit aggregation-induced/enhanced emission characteristics with high quantum yields up to 74.0% in the solid state, and are thermally stable, showing high degradation temperatures and melting points up to 388 and 246 °C, respectively. Thanks to the contained A or D moieties, the siloles show intriguing solvatochromism: DMTPS-ALD exhibits almost no response to solvents due to the balance of electron affinities of the aldehyde and the silole core. Whereas, DMTPS-DCV and DMTPS-DPA possess outward intramolecular charge-transfer (ICT) from the silole core and the phenyl rings on its 3,4-positions to dicyanovinyl groups, and inward ICT from diphenylamine groups to the silole core, respectively, showing positive solvatochromism. A multilayer organic light-emitting diode using DMTPS-DPA among the luminogens as an emitter layer shows the highest performance with turn-on voltage, maximum luminance, current, power, and external efficiencies of 3.1 V, 13405 cd m−2, 8.28 cd A−1, 7.88 lm W−1, and 2.42%, respectively. Furthermore, DMTPS-DPA can also serve in hole-transporting layers because of its high hole-mobility. Therefore, the incorporation of a triphenylamine moiety into a silole system not only changes the classical aggregation-caused quenching fluorophore into AEE-active DMTPS-DPA, another example of “turning stone into gold”, but also enhances the hole-transporting ability of siloles.
Co-reporter:Hongkun Li, Jian Wang, Jing Zhi Sun, Rongrong Hu, Anjun Qin and Ben Zhong Tang
Polymer Chemistry 2012 vol. 3(Issue 4) pp:1075-1083
Publication Date(Web):17 Feb 2012
DOI:10.1039/C2PY00586G
Azide–alkyne click polymerization is generally catalyzed by the Cu(I) complex, in which the removal of metallic residues after reaction remains challengeable. In this work, a metal-free click polymerization method was developed to avoid this problem. The diazide monomers (9 and 10) could readily react with aromatic and aliphatic dipropiolates (1 and 2) under simple heating to produce functional poly(aroxycarbonyltriazole)s (PACTs), a kind of polyester, with high molecular weights (Mw up to 23500) and regioregularities (fraction of 1,4-disubstituted 1,2,3-triazole in polymers up to ∼90%) in excellent yields (up to ∼99%). The metal-free click polymerization also propagates smoothly in an open atmosphere without protection from oxygen and moisture. The PACTs are thermally stable, with 5% loss of their weights at temperatures higher than 335 °C. Thanks to the contained ester groups, the polymers can be rapidly degraded in the presence of potassium hydroxide aqueous solution. The PACT containing tetraphenylethene units exhibits a unique feature of aggregation-induced emission and can function as a fluorescent chemosensor to detect explosives in a superamplified manner.
Co-reporter:Qiang Wei;Haiqin Deng;Yunbo Cai;Jacky W. Y. Lam;Jie Li;Jingzhi Sun;Meng Gao;Ben Zhong Tang
Macromolecular Rapid Communications 2012 Volume 33( Issue 16) pp:1356-1361
Publication Date(Web):
DOI:10.1002/marc.201200212
Abstract
The 1,3-dipolar cycloaddition of azides and active internal alkynes has been well studied, but is rarely utilized as a tool for polymer preparation. In this work, an efficient polymerization route is developed. Polycycloaddition of diazide (4) and bis(benzoylethynyl)-benzenes and -butane (3) at elevated temperature has produced the first examples of soluble 1,4,5-trisubstituted polytriazoles PI with satisfactory molecular weights (Mw up to 16 400) in excellent yields (up to 98.6%). All the obtained polymers are thermally stable, losing merely 5% of their weights at temperatures higher than 367 °C. They exhibit higher refractive indices than some commercial plastics and can be crosslinked upon UV irradiation to generate a 3D photopattern with high resolution. The metal-free feature of such a methodology offers a facile tool to prepare functional materials free from the contamination of metal species.
Co-reporter:Tianxiang Wang;Yunbo Cai;Zhipeng Wang;Erjia Guan;Dahai Yu;Jingzhi Sun;Ben Zhong Tang;Changyou Gao
Macromolecular Rapid Communications 2012 Volume 33( Issue 18) pp:1584-1589
Publication Date(Web):
DOI:10.1002/marc.201200324
Abstract
Tetraphenylethylene (TPE)-substituted poly(allylamine hydrochloride) (PAH-g-TPE) is synthesized by a Schiff base reaction between PAH and TPE-CHO. The PAH-g-TPE forms micelles in water at pH 6, which are further transformed into pure TPE-CHO nanoparticles (NPs) with a diameter of ≈300 nm after incubation in a solution of low pH value. In contrast, only amorphous precipitates are obtained when TPE-CHO methanol solution is incubated in water. The aggregation-induced emission feature of the TPE molecule is completely retained in the TPE NPs, which can be internalized into cells and show blue fluorescence. Formation mechanism of the TPE NPs is proposed by taking into account the guidance effect of linear and charged PAH molecules, and the propeller-stacking manner between the TPE-CHO molecules.
Co-reporter:Jian Wang, Ju Mei, Engui Zhao, Zhegang Song, Anjun Qin, Jing Zhi Sun, and Ben Zhong Tang
Macromolecules 2012 Volume 45(Issue 19) pp:7692-7703
Publication Date(Web):September 24, 2012
DOI:10.1021/ma3017037
Cu(I)-catalyzed azide–alkyne click polymerization, developed based on the click reaction, has become a powerful tool for the construction of functional polytriazoles with linear and hyperbranched structures. This method has, however, rarely been used for the preparation of functional hyperbranched conjugated polytriazoles (hb-CPTA). In this paper, soluble ethynyl-capped hb-CPTA with weight-averaged molecular weight of 39 500 was synthesized in high yield (84.4%) by the Cu(I)-catalyzed azide–alkyne click polymerization of tetraphenylethene containing diazide [1,2-bis(4-azidophenyl)-1,2-diphenylethene] and tetrayne [1,1,2,2-tetrakis(4-ethynylphenyl)ethane] in equal concentration. By taking advantage of the ethynyl groups on its periphery, the polymer could be efficiently postfunctionalized by azide–alkyne and thiol–yne click reactions. The polymers are thermally stable and loss 5% of their weights at temperatures higher than 340.0 °C. hb-CPTA also possesses high char yield (74.8%) at 800 °C. The polymers feature the unique characteristics of aggregation-enhanced emission. Furthermore, the PL intensities of the hb-CPTA and thiol–yne postfunctionalized polytriazoles increase linearly with water fraction in THF/water mixtures. Thanks to their rigid structures, the polymers could be fabricated into unimolecular nanoparticles with sizes of ca. 100 nm. Thus, this paper provides a powerful method to synthesize soluble ethynyl-capped hyperbranched polymers, which could be a useful platform for preparation of versatile functional polymers via postreactions.
Co-reporter:Hong-kun Li;Jing-zhi Sun;An-jun Qin 秦安军
Chinese Journal of Polymer Science 2012 Volume 30( Issue 1) pp:1-15
Publication Date(Web):2012 January
DOI:10.1007/s10118-012-1098-2
The great achievements of click chemistry have encouraged polymer scientists to use this reaction in their field. This review assembles an update of the advances of using azide-alkyne click polymerization to prepare functional polytriazoles (PTAs) with linear and hyperbranched structures. The Cu(I)-mediated click polymerization furnishes 1,4-regioregular PTAs, whereas, the metal-free click polymerization of propiolates and azides produces PTAs with 1,4-regioisomer contents up to 90%. The PTAs display advanced functions, such as aggregation-induced emission, thermal stability, biocompatibility and optical nonlinearity.
Co-reporter:AnJun Qin;Ya Zhang;Ning Han;Ju Mei;JingZhi Sun;WeiMin Fan
Science China Chemistry 2012 Volume 55( Issue 5) pp:772-778
Publication Date(Web):2012 May
DOI:10.1007/s11426-012-4528-7
An amphiphilic polymer bearing tetraphenylethene (TPE) moiety was synthesized by convenient reactions. The polymer exhibits unique aggregation-induced emission (AIE) characteristics and can self-assemble to size-tunable particles in DMF/water mixtures. The polymer nanoparticles can be used for cell imaging, which provides a potential stable fluorescent tool to monitor the distribution of drugs and bioconjugates in living cells.
Co-reporter:Jian Wang, Ju Mei, Wangzhang Yuan, Ping Lu, Anjun Qin, Jingzhi Sun, Yuguang Ma and Ben Zhong Tang
Journal of Materials Chemistry A 2011 vol. 21(Issue 12) pp:4056-4059
Publication Date(Web):09 Feb 2011
DOI:10.1039/C0JM04100A
Hyperbranched polytriazoles with spring-like architectures exhibit the feature of aggregation-induced emission (AIE) due to the high compressibility of polymer spheres from solution to aggregate. Thanks to their AIE effect, the polymer nanoaggregates can detect explosives with superamplification effect.
Co-reporter:Yi Liu; Anjun Qin;Xiujuan Chen;Xiao Yuan Shen;Li Tong;Rongrong Hu; Jing Zhi Sun; Ben Zhong Tang
Chemistry - A European Journal 2011 Volume 17( Issue 52) pp:14736-14740
Publication Date(Web):
DOI:10.1002/chem.201102613
Co-reporter:HongKun Li;Ju Mei;Jian Wang;Shuang Zhang;QiuLi Zhao
Science China Chemistry 2011 Volume 54( Issue 4) pp:
Publication Date(Web):2011 April
DOI:10.1007/s11426-011-4235-9
Regioseletive 1,3-dipolar polycycloadditions of 4,4′-isopropylidenediphenyl dipropiolate (1) and tetraphenylethene (TPE)-containing diazides (2) are carried out in polar solvents such as DMF/toluene at a moderate temperature of 100 °C for 6 h, producing poly(aroxycarbonyltriazole)s (PACTs) P3 with high molecular weights (Mw up to 23900) and regioregularities (F1,4 up to ∼90%) in high yields (up to ∼99%). These metal-free click polymerizations can propagate smoothly in an open atmosphere without protection from oxygen and moisture. The obtained polymers are soluble in common organic solvents and thermally stable at temperatures up to 375 °C. Thanks to their contained TPE moieties, the PACTs show aggregation-induced emission and can serve as fluorescent chemosensors for superamplified detection of explosives.
Co-reporter:Anjun Qin;Jacky W. Y. Lam;Cathy K. W. Jim;Ben Zhong Tang
Macromolecular Symposia 2009 Volume 279( Issue 1) pp:7-13
Publication Date(Web):
DOI:10.1002/masy.200950502
Abstract
Functional poly(aroyltriazoles) (PATAs) were synthesized by heating mixtures of bis(aroylacetylene)s and diazides in polar solvents such as DMF/toluene at a moderate temperature of 100 °C with high molecular weights (Mw up to 17 200) and regioregularities (1,4-regioisomeric ratio up to ∼95%) in high yields (up to ∼95%). The obtained polymers are soluble in common organic solvents and are thermally stable. The PATAs containing triphenylamine units emit visible light and show unique solvatochromism, exhibiting large two-photon absorption cross sections due to the intramolecular charge transfer between their electron-donating triphenylamine and electron-accepting aroyltriazole units. The tetraphenylethene (TPE)-functionalized polymer shows intriguing aggregation-induced emission phenomenon, that is, the polymer is weakly emissive in its solution state but emit strongly in its aggregate/solid state with quantum yield of ∼7.1%.
Co-reporter:Haoke Zhang, Hongkun Li, Jia Wang, Jingzhi Sun, Anjun Qin and Ben Zhong Tang
Journal of Materials Chemistry A 2015 - vol. 3(Issue 20) pp:NaN5166-5166
Publication Date(Web):2015/04/10
DOI:10.1039/C5TC00629E
Axial chiral aggregation-induced emission (AIE) luminogens of (R)-3,3′-BTPE-BINA, (R)-6,6′-BTPE-BINA and (S)-6,6′-BTPE-BINA were synthesized for the first time by covalently attaching the AIE-active tetraphenylethene (TPE) units to the axial chiral binaphthol (BINOL) moieties at their 3,3′- or 6,6′-positions. It was found that the circular dichroism (CD) value when TPE was attached to BINOL at its 3,3′-positions was much larger than that found after its attachment at 6,6′-positions. The resultant AIE-active luminogens (AIEgens) show high quantum yields (up to 42.4%) in their aggregated states. Interestingly, these AIEgens exhibit an abnormal aggregation-annihilation CD (AACD) phenomenon. The decrease in the twisted angle between the two naphthalene rings upon aggregation was rationalized as the cause of this unique effect.
Co-reporter:Ming Chen, Han Nie, Bo Song, Lingzhi Li, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Journal of Materials Chemistry A 2016 - vol. 4(Issue 14) pp:NaN2908-2908
Publication Date(Web):2015/11/18
DOI:10.1039/C5TC03299G
Aggregation-induced emission (AIE) is a unique photo-physical phenomenon and has become an emerging and hot research area. With the enthusiastic efforts paid by researchers, hundreds of AIE-active luminogens (AIEgens) have been generated but heterocyclic AIEgens are rarely reported. Recently, we enriched the family of AIEgens and reported a pyrazine-based AIEgen of tetraphenylpyrazine (TPP), which could be facilely functionalized by a post-synthetic strategy. In this work, we further expanded the TPP-based AIE system by covalently attaching one, two or four electron-donating triphenylamine moieties to the TPP core via Suzuki coupling, and TPP–TPA, TPP–2TPA and TPP–4TPA were produced, respectively. Thanks to their donor-π-acceptor structures, these luminogens exhibit multi-functional properties, such as excellent thermal stability (up to 504 °C), large molar absorptivity, bright emission in the solid state (quantum yields up to 35.2%), solvatochromism, and high two-photon absorption cross-sections (up to 480 GM). Furthermore, using TPP–TPA as the emitting layer, a triple-layer device was fabricated and a turn-on voltage, maximum luminance, current efficiency, power efficiency, and external quantum efficiency of 3.7 V, 17459 cd m−2, 5.49 cd A−1, 3.18 lm W−1 and 2.88% were realized, respectively. These results indicate a huge potential to develop high-tech applications based on these TPP-based AIEgens.
Co-reporter:Jian Wang, Ju Mei, Wangzhang Yuan, Ping Lu, Anjun Qin, Jingzhi Sun, Yuguang Ma and Ben Zhong Tang
Journal of Materials Chemistry A 2011 - vol. 21(Issue 12) pp:NaN4059-4059
Publication Date(Web):2011/02/09
DOI:10.1039/C0JM04100A
Hyperbranched polytriazoles with spring-like architectures exhibit the feature of aggregation-induced emission (AIE) due to the high compressibility of polymer spheres from solution to aggregate. Thanks to their AIE effect, the polymer nanoaggregates can detect explosives with superamplification effect.
Co-reporter:Lingzhi Li, Ming Chen, Haoke Zhang, Han Nie, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2015 - vol. 51(Issue 23) pp:NaN4833-4833
Publication Date(Web):2015/02/04
DOI:10.1039/C5CC00241A
The influence of the number and substitution position of phenyl groups on the aggregation-enhanced emission of benzene-cored luminogens is unambiguously revealed.
Co-reporter:Ming Chen, Lingzhi Li, Han Nie, Jiaqi Tong, Lulin Yan, Bin Xu, Jing Zhi Sun, Wenjing Tian, Zujin Zhao, Anjun Qin and Ben Zhong Tang
Chemical Science (2010-Present) 2015 - vol. 6(Issue 3) pp:NaN1937-1937
Publication Date(Web):2014/12/11
DOI:10.1039/C4SC03365E
Research on aggregation-induced emission (AIE) has been a hot topic. Due to enthusiastic efforts by many researchers, hundreds of AIE luminogens (AIEgens) have been generated which were mainly based on archetypal silole, tetraphenylethene, distyrylanthracene, triphenylethene, and tetraphenyl-1,4-butadiene, etc. To enlarge the family of AIEgens and to enrich their functions, new AIEgens are in high demand. In this work, we report a new kind of AIEgen based on tetraphenylpyrazine (TPP), which could be readily prepared under mild reaction conditions. Furthermore, we show that the TPP derivatives possess a good thermal stability and their emission could be fine-tuned by varying the substituents on their phenyl rings. It is anticipated that TPP derivatives could serve as a new type of widely utilized AIEgen, based on their facile preparation, good thermo-, photo- and chemostabilities, and efficient emission.
Co-reporter:Yunbo Cai, Lingzhi Li, Zongtan Wang, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2014 - vol. 50(Issue 64) pp:NaN8895-8895
Publication Date(Web):2014/06/16
DOI:10.1039/C4CC02844A
A novel tetraphenylethene-based fluorescent H2S probe was designed and synthesized, which exhibited high selectivity and tuneable sensitivity, making direct indication of H2S concentration in blood and unknown samples possible.
Co-reporter:Ju Mei, Jian Wang, Jing Zhi Sun, Hui Zhao, Wangzhang Yuan, Chunmei Deng, Shuming Chen, Herman H. Y. Sung, Ping Lu, Anjun Qin, Hoi Sing Kwok, Yuguang Ma, Ian D. Williams and Ben Zhong Tang
Chemical Science (2010-Present) 2012 - vol. 3(Issue 2) pp:NaN558-558
Publication Date(Web):2011/10/25
DOI:10.1039/C1SC00688F
Three dimethyltetraphenylsiloles (DMTPSs) symmetrically substituted on their 2,5-positions with electron-accepting (A), i.e.aldehyde (ALD) and dicyanovinyl (DCV) or donating (D), i.e.diphenylamine (DPA) moieties were designed and synthesized via facile reaction procedures. The propeller-shaped luminogens exhibit aggregation-induced/enhanced emission characteristics with high quantum yields up to 74.0% in the solid state, and are thermally stable, showing high degradation temperatures and melting points up to 388 and 246 °C, respectively. Thanks to the contained A or D moieties, the siloles show intriguing solvatochromism: DMTPS-ALD exhibits almost no response to solvents due to the balance of electron affinities of the aldehyde and the silole core. Whereas, DMTPS-DCV and DMTPS-DPA possess outward intramolecular charge-transfer (ICT) from the silole core and the phenyl rings on its 3,4-positions to dicyanovinyl groups, and inward ICT from diphenylamine groups to the silole core, respectively, showing positive solvatochromism. A multilayer organic light-emitting diode using DMTPS-DPA among the luminogens as an emitter layer shows the highest performance with turn-on voltage, maximum luminance, current, power, and external efficiencies of 3.1 V, 13405 cd m−2, 8.28 cd A−1, 7.88 lm W−1, and 2.42%, respectively. Furthermore, DMTPS-DPA can also serve in hole-transporting layers because of its high hole-mobility. Therefore, the incorporation of a triphenylamine moiety into a silole system not only changes the classical aggregation-caused quenching fluorophore into AEE-active DMTPS-DPA, another example of “turning stone into gold”, but also enhances the hole-transporting ability of siloles.
Co-reporter:Ming Chen, Lingzhi Li, Han Nie, Yang Shi, Ju Mei, Jian Wang, Jing Zhi Sun, Anjun Qin and Ben Zhong Tang
Chemical Communications 2015 - vol. 51(Issue 53) pp:NaN10713-10713
Publication Date(Web):2015/05/20
DOI:10.1039/C5CC03181H
N-type pyrazine-based 1,4- and 1,5-disubstituted 1,2,3-triazole derivatives, showing unique aggregation-enhanced emission characteristics, were facilely prepared via Cu- and Ru-catalysed azide–alkyne cycloadditions, respectively. Thanks to their electron-deficient properties, they could readily form red-emissive charge transfer complexes with electron-donating triphenylamine in the aggregate and solid states.
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