A novel benzotriazole derivate with Twisted intramolecular charge transfer and Aggregation Induced emission features for proton determination

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2022-03, Vol.269, p.120780, Article 120780
• Main Authors: Li, Shaoheng, Shi, Na, Zhang, Mingyu, Chen, Zhaokang, Xia, Daichuan, Zheng, Qingchuan, Feng, Guodong, Song, Zhiguang
• Format: Article
• Language: English
• Subjects: Aggregation-Induced Emission; Benzotriazole; H-aggregate; Proton Response; Twisted Intramolecular Charge Transfer
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2021.120780

[Display omitted] •A novel benzotriazole derivative BTADA with TICT and AIE features is synthesized.•BTADA shows a sensitive and stepwise response to acid in solution and solid state.•BTADA exhibits multiple fluorescence color changes when reacting with acid.•BTADA has a potential application in monitoring acid-generating organic reactions. Molecules with Aggregation-Induced Emission (AIE) effects could show strong emission in solid or aggregate form, thus they are suitable for applications in the field of solid luminescent materials. According to former reporting, AIE molecules are always J-aggregates. In this study, a new benzotriazole derivate with electron donor–acceptor structure was synthesized. (E)-4-(2-(1H-benzo[d] [1,2,3] triazol-1-yl) vinyl)-N, N-dimethylaniline (BTADA) has both TICT and AIE effect, even though it is H-aggregate. Furthermore, BTADA could respond to proton in solution and solid form. Due to its multiple binging sites, proton would bind to benzotriazole and dimethylaniline moiety successively when BTADA was exposed to acid, and the fluorescent color changed from green to yellow then blue as the concentration of proton increased. Such phenomena indicate BTADA has potential usage in proton detection.