Development of novel organophosphorus-containing functional-dye materials

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Novel 6-membered conjugated heterocyclic compounds including a phosphorus atom were investigated. Versatile synthetic methods of these fluorescent phosphinine derivatives have been developed, and the structural effects on physical properties of the synthesized materials were investigated. 4-Substituted symmetric derivatives show relatively high quantum yields. The electronic effects of the substituents at 4-position strongly affect the wavelength of the fluorescence, whereas the substituents at 3-position have less influence. In addition, we also developed a versatile method of organophosphine synthesis for the preparation of the starting materials for the phosphinine synthesis. A conversion process of lambda5-phosphole derivatives to lambda3-derivatives was also achieved.The developed novel heterocyclic compounds are expected to play an important role for the development of organic functional materials.