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2-(4'-氨基-2'-羟基苯基)-1H-咪唑并[4,5-c]吡啶及其类似物的光物理性质:分子内质子转移与分子内电荷转移

Photophysics of 2-(4'-amino-2'-hydroxyphenyl)-1H-imidazo-[4,5-c]pyridine and its analogues: intramolecular proton transfer versus intramolecular charge transfer.

作者信息

Behera Santosh Kumar, Karak Ananda, Krishnamoorthy G

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.

出版信息

J Phys Chem B. 2015 Feb 12;119(6):2330-44. doi: 10.1021/jp5064808. Epub 2014 Nov 5.

DOI:10.1021/jp5064808
PMID:25337987
Abstract

Photophysical characteristics of 2-(4'-amino-2'-hydroxyphenyl)-1H-imidazo-[4,5-c]pyridine (AHPIP-c) have been studied in various aprotic and protic solvents using UV-visible, steady state fluorescence and time-resolved fluorescence spectroscopic techniques. To comprehend the competition between the intramolecular charge transfer (ICT) and the excited state intramolecular proton transfer (ESIPT) processes, the photophysical properties of 2-(4'-amino-2'-methoxyphenyl)-1H-imidazo-[4,5-c]pyridine (AMPIP-c) and 2-(4'-aminophenyl)-1H-imidazo-[4,5-c]pyridine (APIP-c) were also investigated. Though APIP-c displays twisted ICT (TICT) emission in protic solvents, AHPIP-c exhibits normal and tautomer emissions in aprotic as well as in protic solvents due to ESIPT. However, the methoxy derivative, AMPIP-c, emits weak TICT fluorescence in methanol.

摘要

使用紫外可见光谱、稳态荧光光谱和时间分辨荧光光谱技术,在各种非质子溶剂和质子溶剂中研究了2-(4'-氨基-2'-羟基苯基)-1H-咪唑并[4,5-c]吡啶(AHPIP-c)的光物理特性。为了理解分子内电荷转移(ICT)和激发态分子内质子转移(ESIPT)过程之间的竞争,还研究了2-(4'-氨基-2'-甲氧基苯基)-1H-咪唑并[4,5-c]吡啶(AMPIP-c)和2-(4'-氨基苯基)-1H-咪唑并[4,5-c]吡啶(APIP-c)的光物理性质。尽管APIP-c在质子溶剂中显示出扭曲的ICT(TICT)发射,但由于ESIPT,AHPIP-c在非质子溶剂和质子溶剂中均表现出正常和互变异构体发射。然而,甲氧基衍生物AMPIP-c在甲醇中发出微弱的TICT荧光。

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