A novel modular approach to triazole-functionalized phthalocyanines using click chemistry.

摘要: A novel, elegant, and significantly improved protocol for the synthesis of a protected octaacetylene phthalocyanine is described. Inexpensive, mild, environmentally benign iodination 1,2-dibromobenzene subsequent optimized chemoselective palladium-catalyzed cyanation are employed to effectively build up key intermediate 4,5-dibromophthalonitrile in two steps. Introduction tert-butyldimethylsilyl-protected acetylene moieties via Sonogashira cross-coupling provides desired phthalonitrile precursor that, after cyclization, yielded phthalocyanine. Subsequently, situ deprotection “clicking” as highly efficient quantitative route novel class octatriazole-functionalized phthalocyanines. The ability such triazole-derived phthalocyanines form well-defined supramolecular structures upon doping with zinc(II) triflate demonstrated.