J. Jaung, M. Matsuoka, K. Fukunishi
Jun 1, 1996
Citations
0
Influential Citations
46
Citations
Journal
Dyes and Pigments
Abstract
Abstract Reaction of 2,3-dicyano-5-methylpyrazine derivatives ( 3a-e ) with arylaldehydes gave new fluorescent styryl dyes ( 4–8 ). These styryl dyes have extended π-conjugated systems and are strong intramolecular charge-transfer chromophoric systems. They are of interest as non-linear optical materials, which should produce a large dipole moment in the excited state, and consequently induce large dipole moment differences accompanying laser irradiation. The styryl dyes derived from 2,3-dicyano-6-hydroxy-5-methylpyrazine showed large solvatochromism, depending on the polarity of the solvent, due to tautomerism between the hydroxypyrazine and the pyridone forms. The fluorescence and solvatochromism properties of dyes 4–8 were also studied, and structure-property relationships in solution and in the solid state were evaluated on the basis of molecular stacking in the solid state.