Geminal Cross Coupling (GCC) Reaction for AIE Materials
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摘要
Tetraphenylethylene(TPE) derivatives are typical aggregation-induced emission(AIE) molecules, which have been widely investigated and applicated. The Rathore's procedures and McMurry reaction are the two frequently used methods for synthesizing the TPE derivatives. The complex processes and low tolerance of active function groups make the TPE with limited structures and properties in some degree. Very recently, a novel strategy, named geminal cross coupling(GCC) reaction, is developed for designing and synthesizing various topological small molecules and polymers with rich optical properties beyond simple TPE compounds, and becomes a powerful synthesis method to AIE materials. This review overviews the current progresses of AIE molecules and polymers prepared by GCC as well as their applications. We believe that GCC reaction will have a bright future in the development of the next generation of tetraarylethylene(TAE)-kind AIE materials.
Tetraphenylethylene(TPE) derivatives are typical aggregation-induced emission(AIE) molecules, which have been widely investigated and applicated. The Rathore's procedures and McMurry reaction are the two frequently used methods for synthesizing the TPE derivatives. The complex processes and low tolerance of active function groups make the TPE with limited structures and properties in some degree. Very recently, a novel strategy, named geminal cross coupling(GCC) reaction, is developed for designing and synthesizing various topological small molecules and polymers with rich optical properties beyond simple TPE compounds, and becomes a powerful synthesis method to AIE materials. This review overviews the current progresses of AIE molecules and polymers prepared by GCC as well as their applications. We believe that GCC reaction will have a bright future in the development of the next generation of tetraarylethylene(TAE)-kind AIE materials.
Tetraphenylethylene(TPE) derivatives are typical aggregation-induced emission(AIE) molecules, which have been widely investigated and applicated. The Rathore's procedures and McMurry reaction are the two frequently used methods for synthesizing the TPE derivatives. The complex processes and low tolerance of active function groups make the TPE with limited structures and properties in some degree. Very recently, a novel strategy, named geminal cross coupling(GCC) reaction, is developed for designing and synthesizing various topological small molecules and polymers with rich optical properties beyond simple TPE compounds, and becomes a powerful synthesis method to AIE materials. This review overviews the current progresses of AIE molecules and polymers prepared by GCC as well as their applications. We believe that GCC reaction will have a bright future in the development of the next generation of tetraarylethylene(TAE)-kind AIE materials.
引文
1 Luo, J.; Xie,Z.; Lam,J. W. Y.; Cheng, L.; Chen,H.; Qiu,C.;Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole.Chem. Commun. 2001, 1740-174.
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4 Li, Z.; Dong, Y.; Mi, B.; Tang, Y.; Haussler, M.; Tong, H.;Dong, Y.; Lam, J. W. Y.; Ren, Y.; Sung, H. H. Y.; Wong, K.S.; Gao, P.; Williams, I. D.; Kwok, H. S.; Tang, B. Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials. J. Phys. Chem. B 2005,109, 10061-10066.
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6 Liu, Y.; Chen,S.; Lam,J. W. Y.; Lu, P.; Kwok,R. T. K.;Mahtab, F.; Kwok, H. S.; Tang, B. Z. Tuning the electronic nature of aggregation-induced emission luminogens with enhanced hole-transporting property. Chem. Mater. 2011, 23,2536-2544.
7 Liu, Y.; Deng, C.; Tang, L.; Qin, A.; Hu, R.; Sun, J. Z.; Tang,B. Z. Specific detection of D-glucose by a tetraphenylethenebased fluorescent sensor. J. Am. Chem. Soc. 2011,133,660-663.
8 Liu,J.; Zhong,Y.; Lam,J. W. Y.; Lu,P.; Hong,Y.; Yu,Y.;Yue, Y.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong, K.S.; Tang, B. Z. Hyperbranched conjugated polysiloles:Synthesis, structure, aggregation-enhanced emission, multicolor fluorescent photopatterning, and superamplified detection of explosives. Macromolecules 2010, 43, 4921-4936.
9 Chen, S.; Liu,J.; Liu,Y.; Su,H.; Hong, Y.; Jim, C. K. W.;Kwok,R.T.K.;Zhao,N.;Qin,W.;Lam,J.W.Y.;Wong,K.S.; Tang, B. Z. An AIE-active hemicyanine fluorogen with stimuli-responsive red/blue emission:Extending the pH sensing range by"switch+knob"effect. Chem. Sci. 2012, 3,1804-1809.
10 Peng,L.; Zhang, G.; Zhang,D.; Xiang,J.; Zhao, R.; Wang, Y.;Zhu, D. Fluorescence"turn-on"ensemble for acetylcholinesterase activity assay and inhibitor screening. Org. Lett. 2009,11, 4014-4017.
11 Hong, Y.; Meng, L.; Chen, S.; Leung, C. W. T.; Da, L. T.; Faisal, M.; Silva, D. A.; Liu, J.; Lam, J. W. Y.; Huang, X.; Tang, B.Z. Monitoring and inhibition of insulin fibrillation by a small organic fluorogen with aggregation-induced emission characteristics. J. Am:Chem. Soc:2012, 134, 1680-1689.
12 Shi, H.; Liu, J.; Geng, J.; Tang, B. Z.; Liu, B. Specific detection of integrinαvβ3 by light-up bioprobe with aggregation-induced emission characteristics. J. Am. Chem. Soc. 2012, 134,9569-9572.
13 Shi, H.; Kwok, R. T. K.; Liu, J.; Xing, B.; Tang, B. Z.; Liu, B.Real-time monitoring of cell apoptosis and drug screening using fluorescent light-up probe with aggregation-induced emission characteristics. J. Am. Chem. Soc. 2012. 134,17972-17981.
14 Yuan, Y.; Kwok, R. T. K.; Tang, B. Z.; Liu, B. Targeted theranostic platinum(IV)prodrug with a built-in aggregation-induced emission light-up apoptosis sensor for noninvasive early evaluation of its therapeutic responses in situ. J. Am. Chem.Soc. 2014,136, 2546-2554.
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20 McMurry, J. E. Titanium-induced dicarbonyl-coupling reactions. Acc. Chem. Res. 1983, 16, 405-411.
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2 An, B. K.; Kwon, S. K.; Jung, S. D.; Park, S. Y. Enhanced emission and its switching in fluorescent organic nanoparticles,J. Am. Chem. Soc. 2002,124, 14410-14415.
3 Tang, B. Z.; Zhan, X.; Yu, G.; Sze Lee, P. P.; Liu, Y.; Zhu, D.Efficient blue emission from siloles. J. Mater. Chem. 2001, 11,2974-2978.
4 Li, Z.; Dong, Y.; Mi, B.; Tang, Y.; Haussler, M.; Tong, H.;Dong, Y.; Lam, J. W. Y.; Ren, Y.; Sung, H. H. Y.; Wong, K.S.; Gao, P.; Williams, I. D.; Kwok, H. S.; Tang, B. Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials. J. Phys. Chem. B 2005,109, 10061-10066.
5 Zhao, Z.; Chen, S.; Lam, J. W. Y.; Jim, C. K. W.; Chan, C. Y.K.; Wang,Z.; Lu,P.; Deng,C.; Kwok,H. S.; Ma,Y.; Tang,B.Z. Steric hindrance,electronic communication,and energy transfer in the photo-and electroluminescence processes of aggregation-induced emission luminogens. J. Phys. Chem. C2010,114, 7963-7972.
6 Liu, Y.; Chen,S.; Lam,J. W. Y.; Lu, P.; Kwok,R. T. K.;Mahtab, F.; Kwok, H. S.; Tang, B. Z. Tuning the electronic nature of aggregation-induced emission luminogens with enhanced hole-transporting property. Chem. Mater. 2011, 23,2536-2544.
7 Liu, Y.; Deng, C.; Tang, L.; Qin, A.; Hu, R.; Sun, J. Z.; Tang,B. Z. Specific detection of D-glucose by a tetraphenylethenebased fluorescent sensor. J. Am. Chem. Soc. 2011,133,660-663.
8 Liu,J.; Zhong,Y.; Lam,J. W. Y.; Lu,P.; Hong,Y.; Yu,Y.;Yue, Y.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong, K.S.; Tang, B. Z. Hyperbranched conjugated polysiloles:Synthesis, structure, aggregation-enhanced emission, multicolor fluorescent photopatterning, and superamplified detection of explosives. Macromolecules 2010, 43, 4921-4936.
9 Chen, S.; Liu,J.; Liu,Y.; Su,H.; Hong, Y.; Jim, C. K. W.;Kwok,R.T.K.;Zhao,N.;Qin,W.;Lam,J.W.Y.;Wong,K.S.; Tang, B. Z. An AIE-active hemicyanine fluorogen with stimuli-responsive red/blue emission:Extending the pH sensing range by"switch+knob"effect. Chem. Sci. 2012, 3,1804-1809.
10 Peng,L.; Zhang, G.; Zhang,D.; Xiang,J.; Zhao, R.; Wang, Y.;Zhu, D. Fluorescence"turn-on"ensemble for acetylcholinesterase activity assay and inhibitor screening. Org. Lett. 2009,11, 4014-4017.
11 Hong, Y.; Meng, L.; Chen, S.; Leung, C. W. T.; Da, L. T.; Faisal, M.; Silva, D. A.; Liu, J.; Lam, J. W. Y.; Huang, X.; Tang, B.Z. Monitoring and inhibition of insulin fibrillation by a small organic fluorogen with aggregation-induced emission characteristics. J. Am:Chem. Soc:2012, 134, 1680-1689.
12 Shi, H.; Liu, J.; Geng, J.; Tang, B. Z.; Liu, B. Specific detection of integrinαvβ3 by light-up bioprobe with aggregation-induced emission characteristics. J. Am. Chem. Soc. 2012, 134,9569-9572.
13 Shi, H.; Kwok, R. T. K.; Liu, J.; Xing, B.; Tang, B. Z.; Liu, B.Real-time monitoring of cell apoptosis and drug screening using fluorescent light-up probe with aggregation-induced emission characteristics. J. Am. Chem. Soc. 2012. 134,17972-17981.
14 Yuan, Y.; Kwok, R. T. K.; Tang, B. Z.; Liu, B. Targeted theranostic platinum(IV)prodrug with a built-in aggregation-induced emission light-up apoptosis sensor for noninvasive early evaluation of its therapeutic responses in situ. J. Am. Chem.Soc. 2014,136, 2546-2554.
15 Dong,Y.; Xu,B.; Zhang, J.; Tan,X.; Wang,L.; Chen,J.; Lv,H.; Wen, S.; Li, B.; Ye, L.; Zou, B.; Tian, W. Piezochromic luminescence based on the molecular aggregation of 9,10-bis((E)-2-(pyrid-2-yl)vinyl)anthracene. Angew. Chem. Int. Ed.2012, 51, 10782-10785.
16 An, B.-K.; Gierschner, J.; Park, S. Y.π-Conjugated cyanostilbene derivatives:A unique self-assembly motif for molecular nanostructures with enhanced emission and transport. Acc.Chem. Res. 2012, 45, 544-554.
17 Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Bioprobes based on AIE fluorogens. Acc. Chem. Res. 2013, 46, 2441-2453.
18 Banerjee, M. Practical synthesis of unsymmetrical tetraarylethylenes and their application for the preparation of[triphenylethylene-spacer-triphenylethylene] triads. J. Org. Chem.2007, 72, 8054-8061.
19 McMurry, J. E.; Krepski, L. R. Synthesis of unsymmetrical olefins by titanium(0)induced mixed carbonyl coupling. Some comments on the mechanism of the pinacol reaction. J. Org.Chem. 1976, 41, 3929-3930.
20 McMurry, J. E. Titanium-induced dicarbonyl-coupling reactions. Acc. Chem. Res. 1983, 16, 405-411.
21 Duan, X. F.; Zeng, J.; Lü, J. W.; Zhang, Z. B. Insights into the general and efficient cross McMurry reactions between ketones. J. Org. Chem. 2006, 71, 9873-9876.
22 Zhang, G.-F.; Wang, H.; Aldred, M. P.; Chen, T.; Chen, Z. Q.;Meng, X.; Zhu, M. Q. General synthetic approach toward geminal-substituted tetraarylethene fluorophores with tunable emission properties:X-ray crystallography, aggregation-induced emission and piezofluorochromism. Chem. Mater. 2014, 26,4433-4446.
23 Corey E. J. and Fuchs P. L. A synthetic method for formyl→ethynyl conversion(RCHO→RC≡CH or RC≡CR'). Tetrahedron Lett. 1972, 36, 3769-3772.
24 Mei,J.; Hong,Y.; Lam,J. W. Y.; Qin,A.; Tang,Y.; Tang,B.Z. Aggregation-induced emission:The whole is more brilliant than the parts. Adv:Mater. 2014, 26, 5429-5479.
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