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

被引：14

作者：

Hagimori, Masayori ^{[1
]}

Shigemitsu, Yasuhiro ^{[2
,3
]}

Murakami, Ryo ^{[4
]}

Yokota, Kenichirou ^{[4
]}

Nishimura, Yasuhisa ^{[4
]}

Mizuyama, Naoko ^{[5
]}

Wang, Bo-Cheng ^{[6
]}

Tai, Chen-Kuen ^{[6
]}

Wang, San-Lang ^{[6
]}

Shih, Tzenge-Lien ^{[6
]}

Wu, Kuen-Da ^{[6
]}

Huang, Zhi-Shuan ^{[6
]}

Tseng, Shih-Chuw ^{[6
]}

Lu, Jian-Wei ^{[6
]}

Wei, Ho-Hsiang ^{[6
]}

Nagaoka, Junko ^{[3
]}

Mukai, Takahiro ^{[1
]}

Kawashima, Shinichi ^{[7
]}

Kawashima, Keisuke ^{[7
]}

Tominaga, Yoshinori ^{[4
]}

机构：

[1] Kobe Pharmaceut Univ, Higashinada Ku, 4-19-1 Motoyamakita Machi, Kobe, Hyogo 6588558, Japan

[2] Ind Technol Ctr Nagasaki, Omura, Nagasaki 8560026, Japan

[3] Nagasaki Univ, Grad Sch Engn, Nagasaki 8528131, Japan

[4] Nagasaki Univ, Fac Environm Studies, Nagasaki 8528521, Japan

[5] Fdn Biomed Res & Innovat, Dept Clin Trial Management, Chuo Ku, Kobe, Hyogo 6500047, Japan

[6] Tamkang Univ, Dept Chem, New Taipei 251, Taiwan

[7] Harima Chem Inc, Kakogawa, Hyogo 6750019, Japan

来源：

DYES AND PIGMENTS | 2016年 / 124卷

关键词：

2-Pyridone; 6-(4-dialkylamino)phenylpyridone; Fluorescence in solution; One-pot synthesis; Ketene dithioacetal; Solvatofluorochromism; DERIVATIVES; DESIGN; FUNGUS;

D O I：

10.1016/j.dyepig.2015.09.017

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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 (0: 0.80-0.92) and dichloromethane (Phi: 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 (Phi: 0.86-0.95) and acetonitrile (Phi: 0.59-0:88). These results indicate that 2-pyridone-based compounds have great potential as fluorophores for various practical applications. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：196 / 202

页数：7

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