Syntheses and characterization of new styryl fluorescent dyes from DAMN. Part II

Jae Yun Jaung, Masaru Matsuoka, Koushi Fukunishi

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Abstract

2,3-Bis(bromomethyl)-5,6-dicyanopyrazine (3) can be prepared more readily by the condensation of DAMN (1) and 1,4-dibromobutane-2,3-dione (2) than by direct bromination of 2,3-dimethyl-5,6-dicyanopyrazine. The Wittig reaction of 3 with arylaldehydes gave a new type of fluorescent styryl dyes (6-8). These styryl dyes have extended π-conjugation systems and strong intramolecular charge-transfer chromophoric systems. They have strong fluorescence in solution and some have fluorescence even in the solid state, which is very important to evaluate their electroluminescence (EL) property as the emitter for EL devices. Calculation of excitation energies using the PPP-MO method, and optimization of their structures using the MOPAC with the PM 3 method were conducted, and their spectral properties are discussed to correlate their functionalities with chemical structures.

Original languageEnglish
Pages (from-to)255-266
Number of pages12
JournalDyes and Pigments
Volume34
Issue number4
DOIs
Publication statusPublished - 1997 Aug

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Keywords

  • Diaminomaleonitrile
  • Dicyanopyrazine
  • Electroluminescence
  • Solid state fluorescence
  • Styryl fluorescent dye
  • Wittig reaction

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