Please use this identifier to cite or link to this item: https://doi.org/10.1002/anie.201600244
Title: Structure-Dependent cis/trans Isomerization of Tetraphenylethene Derivatives: Consequences for Aggregation-Induced Emission
Authors: Zhang, Chong-Jing 
Feng, Guangxue 
Xu, Shidang 
Zhu, Zhenshu 
Lu, Xianmao 
Wu, Jien 
Liu, Bin 
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
aggregation induced emission
fluorescent probes
imaging agents
isomerization
LIGHT-UP PROBE
PHOTODYNAMIC THERAPY
AIE LUMINOGEN
CANCER-CELLS
E/Z ISOMERS
RESPONSES
BIOPROBE
Issue Date: 17-May-2016
Publisher: WILEY-V C H VERLAG GMBH
Citation: Zhang, Chong-Jing, Feng, Guangxue, Xu, Shidang, Zhu, Zhenshu, Lu, Xianmao, Wu, Jien, Liu, Bin (2016-05-17). Structure-Dependent cis/trans Isomerization of Tetraphenylethene Derivatives: Consequences for Aggregation-Induced Emission. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (21) : 6192-6196. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.201600244
Abstract: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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. The cis and trans isomers of a tetraphenylethene derivative with aggregation-induced emission, TPETH-MAL, were characterized by HPLC analysis and NMR spectroscopy. cis-TPETH-MAL emits yellow fluorescence in DMSO at -20 °C whereas trans-TPETH-MAL shows red fluorescence under the same conditions.
Source Title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
URI: https://scholarbank.nus.edu.sg/handle/10635/169701
ISSN: 14337851
15213773
DOI: 10.1002/anie.201600244
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