Syntheses and thermal properties of 5,10-disubstituted-2,3,7,8-tetracyano-5,10-dihydrodipyrazino[2,3-b:2′,3′-e]pyrazines and polymeric porphyrazines derived from 2,3-dichloro-5,6-dicyanopyrazine

Abstract

Intermolecular cyclization of 2-alkylamino-3-chloro-5,6-dicyanopyrazine2 in the presence of tributylamine in N,N-dimethylformamide (DMF) gave 5,10-disubstituted-2,3,7,8-tetracyano-5,10-dihydrodipyrazino[2,3-b:2′,3′-e]pyrazines3, which showed strong mesomorphic property and were anticipated as new chromophoric system for functional dye materials. Absorption spectra, fluorescent properties and other physical properties were correlated with their chemical structures. Vanadyl oligomeric porphyrazine with long alkyl groups synthesized from3 had satisfactory solubility in tetrahydrofuran (THF), diethyl ether and dimethylsulfoxide (DMSO). The syntheses and characterization of vanadyl polymeric porphyrazines derived from3 with long alkyl groups are reported.