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■ Synthesis and Solvatochromic Behavior of Stilbazolium Merocyanine-Type Dyes Having a Benzo[c]quinolizinium Ring

Sadao Arai,* Hitoshi Arai, Mitsuhiko Hida, and Takamichi Yamagishi

*Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University, 1-1, Minami-ohsawa, Hachioji, Tokyo 192-0364, Japan

Abstract

A series of stilbazolium merocyanine-type dyes, 3[2-(hydroxy-substituted aryl)vinyl]benzo[c]quinolizinium perchlorates, was synthesized by the aldol-type condensation of 3-methylbeno[c]quinolizinium perchlorate with hydroxy-substituted benzaldehyde derivatives in 45-85% yields. The deprotonated from of the dyes exhibited the pronounced negative solvatochromism extended almost over the whole visible region. The negative solvatochromic character of the dyes having a benzo[c]quinolizinium ring was more striking than that of the isomeric dyes having a benzo[a]quinolizinium ring.