Angewandte Chemie - International Edition p. 6192 - 6196 (2016)
Update date:2022-08-03
Topics:
Zhang, Chong-Jing
Feng, Guangxue
Xu, Shidang
Zhu, Zhenshu
Lu, Xianmao
Wu, Jien
Liu, Bin
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.
View MoreJunkai (Tianjin) Chemical Co., Ltd.
website:http://www.junkaichem.com
Contact:86-22-85689515
Address:Room 8-501, Building K2, The Hi-Tech Green Industrial Base, No.6, 6th Road, Hi-Tech Development Road, Tianjin Hi-Tech IndustrialPark, Tianjin, China.
Shanghai Sinofluoro Scientific Co., Ltd
Contact:+86-21-64279360
Address:Room 1006,Building 3,#58 East Xinjian Road, Shanghai ,201100,China,
Beijing Tianjia Chemical Science & Technology Co.,Ltd
Contact:86-0550-2392698
Address:No.388, Shiliang Road (East),
Zhuzhou Farshine Chemical Industry Co., Ltd
Contact:0086-731-28482786
Address:No. 1,Shui Xian Road, He Tang Dictrict,Hunan-412000,China
Shanghai Harvest Chemical Ind. Co., Ltd.
Contact:021-51385350
Address:ROOM 806-807, AI LI CHEN BUILDING, No.333 JINGXIANG ROAD, PUDONG DISTRICT, 201206, SHANGHAI
Doi:10.1002/anie.200701984
(2007)Doi:10.1021/ja075967i
(2007)Doi:10.1021/om7006216
(2007)Doi:10.1016/j.bmcl.2010.04.013
(2010)Doi:10.1246/cl.1985.53
(1985)Doi:10.1021/ja00306a051
(1985)