2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state

doi:10.1016/j.dyepig.2015.09.017

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Title:	2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state
Authors:	Masayori Hagimori;Yasuhiro Shigemitsu;Ryo Murakami;Kenichirou Yokota;Yasuhisa Nishimura;Naoko Mizuyama;Bo-Cheng Wang;Chen-Kuen Tai;San-Lang Wang;Tzenge-Lien Shih;Kuen-Da Wu;Zhi-Shuan Huang;Shih-Chuw Tseng;Jian-Wei Lu;Ho-Hsiang Wei;Junko Nagaoka;Takahiro Mukai;Shinichi Kawashima;Keisuke Kawashima;Yoshinori Tominaga
Keywords:	2-Pyridone;6-(4-dialkylamino)phenylpyridone;Fluorescence in solution;One-pot synthesis;Ketene dithioacetal;Solvatofluorochromism
Date:	2016
Issue Date:	2016-11-10 02:10:35 (UTC+8)
Abstract:	Novel highly emissive 2-pyridone-based compounds 3a,b and 4a–d were synthesized by a convenient one-pot method from 4-(dialkylamino)acetophenones (1a,b) and cyanoketene dithioacetal (2a) or sulfonyl ketene dithioacetals (2b,c), and their fluorescence properties were investigated. A simple structure modification of 2-pyridones significantly affected their optical properties including the emission wavelength and fluorescence intensity. All the 6-(4-dialkylamino)phenyl-2-pyridones showed positive solvatofluorochromism and intense blue-green fluorescence in nonpolar solvents such as chloroform (Ф: 0.80–0.92) and dichloromethane (Ф: 0.83–0.94). A hypsochromic shift of the fluorescence emission maxima and strong fluorescence in a polar solvent were observed by substituting the dimethylamino group with a diethylamino group. Introduction of a sulfonyl group disturbed the molecular planarity of compounds 4a, 4b, and 4d, resulting in a strong fluorescence in acetone (Ф: 0.86–0.95) and acetonitrile (Ф: 0.59–0.88). These results indicate that 2-pyridone-based compounds have great potential as fluorophores for various practical applications.
Relation:	Dyes and Pigments 124, p.196-202
DOI:	10.1016/j.dyepig.2015.09.017
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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