Aggregation-induced emission enhancement of 2-(2′-hydroxyphenyl)benzothiazole-based excited-state intramolecular proton-transfer compounds

被引:224
作者
Qian, Yan
Li, Shayu
Zhang, Guoqi
Wang, Qian
Wang, Shuangqing
Xu, Huijun
Li, Chengzhang
Li, Yi [1 ]
Yang, Guoqiang
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Key Lab Photochem, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100080, Peoples R China
关键词
D O I
10.1021/jp070076i
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A novel class of 2-(2'-hydroxyphenyl)benzothiazole-based (HBT-based) excited-state intramolecular proton-transfer (ESIPT) compounds, N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]isophthalic amide (DHIA) and N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]5-tert-butyl-isophthalic amide (DHBIA) has been feasibly synthesized and the properties of their nanoparticles in THF/H2O mixed solvent were investigated. Both compounds were found to exhibit aggregation-induced emission enhancement (AIEE) due to restricted intramolecular motion and easier intramolecular proton transfer in solid state. On identical experimental conditions, the emission of DHBIA aggregates increased more remarkably than that of DHIA. Different aggregation forms of these two organic compounds, due to the steric hindrance of a single tert-butyl group, could be responsible for the notably different degrees of the fluorescence enhancement. Their aggregation modes were investigated on the basis of time-dependent absorption, scanning electron microscope (SEM) images, and molecular modeling with theoretical calculation. The photophysical dynamics were also depicted based on the extremely fast ESIPT four-level cycle.
引用
收藏
页码:5861 / 5868
页数:8
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