Structure-Dependent cis/trans Isomerization of Tetraphenylethene Derivatives: Consequences for Aggregation-Induced Emission
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- 作者：Dr. Chong-Jing Zhang ; Dr. Guangxue Feng ; Shidang Xu ; Dr. Zhenshu Zhu ; Prof. Dr. Xianmao Lu ; Dr. Jien Wu and Prof. Dr. Bin Liu
- 刊名：Angewandte Chemie
- 出版年：2016
- 出版时间：May 17, 2016
- 年：2016
- 卷：128
- 期：21
- 页码：6300-6304
- 全文大小：2898K
- ISSN：1521-3757
文摘
The isomerization and optical properties of the cis and trans isomers of tetraphenylethene (TPE) derivatives with aggregation-induced emission (AIEgens) have been sparsely explored. We have now observed the tautomerization-induced isomerization of a hydroxy-substituted derivative, TPETH-OH, under acidic but not under basic conditions. Replacing the proton of the hydroxy group in TPETH-OH with an alkyl group leads to the formation of TPETH-MAL, for which the pure cis and trans isomers were obtained and characterized by HPLC analysis and NMR spectroscopy. Importantly, cis-TPETH-MAL emits yellow fluorescence in DMSO at −20 °C whereas trans-TPETH-MAL shows red fluorescence under the same conditions. Moreover, the geometry of cis- and trans-TPETH-MAL remains unchanged when they undergo thiol–ene reactions to form cis- and trans-TPETH-cRGD, respectively. Collectively, our findings improve our fundamental understanding of the cis/trans isomerization and photophysical properties of TPE derivatives, which will guide further AIEgen design for various applications.