The Effect of Substituent Position on Excited State Intramolecular Proton Transfer in Benzoxazinone Derivatives: Experiment and DFT Calculation

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 s...

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Veröffentlicht in:Journal of fluorescence 2017, Vol.27 (1), p.235-242
Hauptverfasser: Bian, Gao-Feng, Guo, Yun, Lv, Xiao-Jing, Zhang, Cheng
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-016-1950-9