Synthesis of 6-(4-diethylamino)phenyl-2-oxo-2H-pyran-3-carbonitorile derivatives and their fluorescence in solid state and in solutions

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.

► We synthesized new 2-pyrone dyes (3a–5a) by a one-pot synthesis reaction with good yields.
► Each compounds exhibited the following fluorescence in the solid state: red (3a), green (4a), and orange (5a).
► In solvents, each compounds exhibit intense fluorescence and show positive solvatochromism.