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Synthesis of 6-(4-diethylamino)phenyl-2-oxo-2H-pyran-3-carbonitorile derivatives and their fluorescence in solid state and in solutions |
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| Authors: | Masayori HagimoriKenichirou Yokota Yasuhisa NishimuraMika Suzuta Chen-Kuen TaiBo-Cheng Wang San-Lang WangTzenge-Lien Shih Kuen-Da WuZhi-Shuan Huang Shih-Chun TsengChieh-Yu Chen Jian-Wei LuHo-Hsiang Wei Keisuke KawashimaShinich Kawashima Yoshinori Tominaga |
| Affiliation: | a Faculty of Pharmaceutical Sciences, Nagasaki International University, 2825-7 Huis Ten Bosch, Sasebo 859-3298, Japan b Department of Pharmacy, Saga University Hospital, 5-1-1 Nabeshima, Saga 849-8521, Japan c Faculty of Environmental Studies, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan d Department of Chemistry, Tamkang University, Tamsui 251, Taiwan e Harima Chemical, Inc., 671-4 Noguchi-machi, Kakogawa 675-0019, Japan |
| Abstract: | One-pot synthesis of a new 2-pyrone dye (3a) by the reaction of 4-diethylamino-acetophenone (1) with methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate (2) in the presence of sodium hydroxide as the base was carried out in DMSO. Compound 4a was synthesized by the replacement of methylsulfanyl group of 3a with dimethylamine at 4-position of pyrone ring. Similarly, compound 5a was prepared via the reaction of 3a with diethyl malonate. Compounds 3a-5a exhibited the following fluorescence in the solid state: red (3a), green (4a), and orange (5a). In addition, it was revealed that 2-pyrone dyes exhibit fluorescence in various solvents and show positive solvatochromism. Compounds 3a and 5a exhibited intense fluorescence in chloroform and dichloromethane (fluorescence quantum yield Φ: 0.94-0.95). In contrast, compound 4a exhibited intense fluorescence in polar solvents (methanol: Φ = 0.92). These 2-pyrone dyes have the potential for applications in various fields. |
| Keywords: | 2-Pyrone dyes One-pot synthesis Ketene dithioacetal Fluorescence Solvatochromism Solid state |
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