Extensive spectral tuning of the proton transfer emission from green to red via a rational derivatization of salicylideneaniline

A series of salicylideneaniline derivatives 1a-lf were synthesized under mild condition in high yields, and characterized by ^1H NMR, HRMS, UV-vis and emission spectra. In solid and aprotic solvents 1a-1f exist mainly as E conformers that possess a sixmembered-ring hydrogen bond and undergo excited-...

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Veröffentlicht in:Chinese chemical letters 2012-11, Vol.23 (11), p.1279-1282
Hauptverfasser: Luo, Ming Hui, Tsai, Hsing Yang, Lin, Hong Yi, Fang, Sin Kai, Chen, Kew Yu
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container_issue 11
container_start_page 1279
container_title Chinese chemical letters
container_volume 23
creator Luo, Ming Hui
Tsai, Hsing Yang
Lin, Hong Yi
Fang, Sin Kai
Chen, Kew Yu
description A series of salicylideneaniline derivatives 1a-lf were synthesized under mild condition in high yields, and characterized by ^1H NMR, HRMS, UV-vis and emission spectra. In solid and aprotic solvents 1a-1f exist mainly as E conformers that possess a sixmembered-ring hydrogen bond and undergo excited-state intramolecular proton transfer (ESIPT) reactions, resulting in a protontransfer tautomer emission. Depending on the electronic donor or acceptor strength of the substituent in either the HOMO or LUMO site, a broad tuning range of the emission from green (1c) to red (1a) has been achieved.
doi_str_mv 10.1016/j.cclet.2012.09.009
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subjects DFT calculations
ESIPT
Salicylideneaniline derivatives
Schiff bases
可见吸收光谱
排放物
激发态分子内质子转移
色变
衍生
调整
非质子溶剂
频谱
title Extensive spectral tuning of the proton transfer emission from green to red via a rational derivatization of salicylideneaniline
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