Dynamics of Solvent Controlled ESIPT of π-Expanded Imidazole Derivatives - pH Effect
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- 作者：J. Jayabharathi (1)
V. Kalaiarasi (1)
V. Thanikachalam (1)
K. Jayamoorthy (1) - 关键词：ESIPT ; DFT ; GSIPT ; TICT ; Monocation
- 刊名：Journal of Fluorescence
- 出版年：2014
- 出版时间：March 2014
- 年：2014
- 卷：24
- 期：2
- 页码：625-637
- 全文大小：3,098 KB
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V. Kalaiarasi (1)
V. Thanikachalam (1)
K. Jayamoorthy (1)
1. Department of Chemistry, Annamalai University, Annamalainagar, 608002, Tamilnadu, India - ISSN：1573-4994
文摘
A set of π-expanded imidazole derivatives employing excited state intramolecular proton transfer (ESIPT) was designed and synthesized. The relationship between the structure and photophysical properties were thoroughly elucidated by comparing with the analogue blocked with ESIPT functionality. The compound possessing an acidic NH function as part of an intramolecular hydrogen bond system has much higher fluorescence quantum yield and Stokes shift and the π-expansion strongly influences the optical properties. The occurrence of ESIPT for imidazole tosylamide derivatives were less affected by the hydrogen-bonding ability of the solvents compared to the unprotected amine. The low pKa values for the monocation ?neutral equilibrium indicate the presence of intramolecular hydrogen bonding between the amino proton and tertiary nitrogen atom.