The Effect of Substituent Position on Excited State Intramolecular Proton Transfer in Benzoxazinone Derivatives: Experiment and DFT Calculation
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- 作者：Gao-Feng Bian ; Yun Guo ; Xiao-Jing Lv ; Cheng Zhang
- 关键词：Benzoxazinone ; ESIPT ; DFT calculation ; Time ; resolved fluorescence spectra ; Solvent effect
- 刊名：Journal of Fluorescence
- 出版年：2017
- 出版时间：January 2017
- 年：2017
- 卷：27
- 期：1
- 页码：235-242
- 全文大小：
- 刊物类别：Biomedical and Life Sciences
- 刊物主题：Biomedicine, general; Biological and Medical Physics, Biophysics; Biotechnology; Biochemistry, general; Analytical Chemistry;
- 出版者：Springer US
- ISSN：1573-4994
- 卷排序：27
文摘
The preparation and the photophysical behaviour of two benzoxazinone derivatives isomers 2-(1-hydroxynaphthalen-2-yl)-4H-benzo[e][1, 3]oxazin-4-one(1) and 2-(3-hydroxynaphthalen-2-yl)-4H-benzo[e][1, 3]oxazin-4-one(2) designed for displaying were reported. The effect of substituent position and solvent effect on the excited state intramolecular proton transfer (ESIPT) dynamics and the spectroscopic properties were investigated using a combined theoretical (i.e., time-dependent density function theory (DFT)) and experimental (i.e., steady-state absorption and emission spectra and time-resolved fluorescence spectra) study. The results showed that compound 1 would facilitate ESIPT process and favored the keto tautomer emission, while compound 2 suppressed the ESIPT process and favored the enol emission.