Synthesis and Solid State Fluorescence of Tricyanofuran Derivatives Containing a 2-Vinylphenol Fragment

Abstract

Reaction of 5-substituted 2-hydroxybenzaldehydes with 2-[3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene]propanedinitrile (tricyanofuran) in ethanol in the presence of ammonium acetate afforded 2-{3-cyano-4-[(E)-2-(2-hydroxyphenyl)ethenyl]-5,5-dimethylfuran-2(5H)-ylidene}propanedinitriles which were found to exhibit solid state fluorescence with the emission maxima ranging from λ 594 to 640 nm. Chromophores containing an alkyl substituent in the benzene ring showed the most intense fluorescence.