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基于 ESIPT 的 2-取代苯并咪唑、苯并恶唑和苯并噻唑荧光衍生物的合成及光物理特性。

Synthesis and photo-physical characteristics of ESIPT inspired 2-substituted benzimidazole, benzoxazole and benzothiazole fluorescent derivatives.

机构信息

Department of Intermediate and Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, 400 019, Maharashtra, India.

出版信息

J Fluoresc. 2012 Jan;22(1):311-22. doi: 10.1007/s10895-011-0962-8. Epub 2011 Sep 29.

DOI:10.1007/s10895-011-0962-8
PMID:21953435
Abstract

Novel 2-(1H-benzimidazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzoxazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzothiazol-2-yl)-5-(N,N-diethylamino) phenol and their derivatives have been synthesized from p-N,N-diethyl amino salicylaldehyde with different substituted o-phenylenediamine or o-aminophenol or o-aminothiophenol and their photo-physical properties were studied. Effects of solvent polarity in the absorption-emission properties of synthesized compounds were investigated. All these compounds shows excited state intra-molecular proton transfer pathway having single absorption and dual emission characteristics. The fluorescent compounds were characterised by FT-IR, (1)HNMR, (13)C NMR and Mass spectral analysis. TGA analysis showed these compounds are thermally stable up to 200 °C.

摘要

新型 2-(1H-苯并咪唑-2-基)-5-(N,N-二乙基氨基)苯酚、2-(1,3-苯并恶唑-2-基)-5-(N,N-二乙基氨基)苯酚、2-(1,3-苯并噻唑-2-基)-5-(N,N-二乙基氨基)苯酚及其衍生物是由对-N,N-二乙基氨基水杨醛与不同取代的邻苯二胺或邻氨基酚或邻氨基噻吩合成的,并研究了它们的光物理性质。考察了溶剂极性对合成化合物吸收-发射性质的影响。所有这些化合物都表现出激发态分子内质子转移途径,具有单吸收和双发射特性。荧光化合物通过傅里叶变换红外光谱(FT-IR)、(1)HNMR、(13)C NMR 和质谱分析进行了表征。热重分析(TGA)表明,这些化合物在 200°C 以下热稳定。

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