2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state
2-Pyridone-based fluorophores containing 4-dialkylamino-phenyl group: Synthesis and fluorescence properties in solutions and in solid state
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DOI：
10.1016/j.dyepig.2015.09.017
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发表时间：
2016-01-01
影响因子：
4.5
通讯作者：
Tominaga, Yoshinori
中科院分区：
文献类型：
--
作者：
Hagimori, Masayori;Shigemitsu, Yasuhiro;Tominaga, Yoshinori
以4-（二烷基氨基）苯乙酮（1a，B）和氰基烯酮二硫缩醛（2a）或磺酰基烯酮二硫缩醛（2B，c）为原料，采用一锅法合成了新型高发射2-吡啶酮化合物3a，B和4a-d，并研究了它们的荧光性质。对2-吡啶酮进行简单的结构修饰，可以显著影响其发光波长和荧光强度等光学性质。在氯仿（0：0.80-0.92）和二氯甲烷（Phi：0.83-0.94）等非极性溶剂中，6-（4-二烷氨基）苯基-2-吡啶酮均表现出正的溶剂化荧光，并发出强烈的蓝绿色荧光。通过用二乙氨基取代二甲氨基，观察到在极性溶剂中荧光发射最大值的蓝移和强荧光。磺酰基的引入扰乱了化合物4a、4 b和4d的分子平面性，导致在丙酮（Phi：0.86-0.95）和乙腈（Phi：0.59-0：88）中的强荧光。这些结果表明，2-吡啶酮基化合物具有很大的潜力，作为荧光团的各种实际应用。(C)2015爱思唯尔有限公司版权所有。
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.