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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: Hagimori, Masayori;Shigemitsu, Yasuhiro;Murakami, Ryo;Yokota, Kenichirou;Nishimura, Yasuhisa;Mizuyama, Naoko;Wang, Bo-Cheng;Tai, Chen-Kuen;Wang, San-Lang;Shih, Tzenge-Lien;Wu, Kuen-Da;Huang, Zhi-Shuan;Tseng, Shih-Chuw;Lu, Jian-Wei;Wei, Ho-Hsiang;Nagaoka, Junko;Mukai, Takahiro;Kawashima, Shinichi;Kawashima, Keisuke;Tominaga, Yoshinori
    Keywords: 2-Pyridone;6-(4-dialkylamino)phenylpyridone;Fluorescence in solution;One-pot synthesis;Ketene dithioacetal;Solvatofluorochromism
    Date: 2016-01
    Issue Date: 2016-01-06 11:06:59 (UTC+8)
    Publisher: Pergamon Press
    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, pp.196-202
    DOI: 10.1016/j.dyepig.2015.09.017
    Appears in Collections:[化學學系暨研究所] 期刊論文

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