Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

被引：51
作者：
Chen, Jun-Sheng [1 ,2 ]
Liu, Run-Ze [1 ,2 ]
Yang, Yang [1 ]
Chu, Tian-Shu [1 ,3 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Qingdao Univ, Inst Computat Sci & Engn, Growing Base State Key Lab, Lab New Fiber & Modern Text, Qingdao 266071, Peoples R China
来源：
THEORETICAL CHEMISTRY ACCOUNTS | 2013年 / 133卷 / 01期
关键词：
Colorimetric sensor; Sensing mechanism; Density functional calculations; Desilylation reaction; Intramolecular charge transfer (ICT); Naphthalimide; FLUORESCENT CHEMOSENSOR; TD-DFT; PROBE; IONS;
D O I：
10.1007/s00214-013-1411-3
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：
The sensing mechanism of a fluoride colorimetric chemosensor 4-(tert-butyldimethylsilyloxy)-N-butyl-naphthalimide has been studied with density functional theory and time-dependent density functional theory methods. The theoretical results suggest that the low barrier of the desilylation reaction is responsible for the rapid response speed to the fluoride anion of the chemosensor. The calculated vertical excitation energies in the ground state of the chemosensor and its desilylation product agree well with the experimental UV-Vis absorbance spectra. It is also found that the intramolecular charge transfer process of the first excited state of the desilylation product induces the redshift of the absorbance and fluorescence spectra of the desilylation product compared with that of the chemosensor. Further, the previously experimentally incorrect assignment of the H-1 NMR spectrum of the desilylation product has been rectified in the present theoretical study.
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页码：1 / 7
页数：7
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