Synthesis and properties of push-pull tetraphyrazinoporphyrazines

Abstract

Pthalocyanines(Pcs), with their two-dimensional 18 pi-electron system and their chemical stability, are attractive due to their various applications in the field of organic light emitting diodes, organic field effect transistor, organic solar cells, and chemosensor[1]. A large number of phthalocyanine derivatives have been synthesized to achieve specific properties. Introduction of two nitrogen atoms into the equivalence of the 1,4-positions of the phthalocyanine benzene units leads to tetraphyrazinoporphyrazines. Owing to the additional nitrogen atoms, Tetraphyrazino- porphyrazines are less electron-rich than the corresponding phthalocyanines. Also, the new types of tetraphyrazinoporphyrazines have been synthesized by substituting 4-bromopheny group and linear alkyl group of the 2,3-position of phyrazine. These molecules behave as push-pull intramolecular charge-transfer chromophoric systems in which substituted groups works as donor and the one or two pyrazine ring as accepter. These results were verified out of our operating computer simulation. Besides, from simple and optimized synthetic methods than usual we could obtain a little more yield of target compound. The synthesized Phthalocyanines(Pcs) derivatives were characterized by UV-visible spectroscopy, MALDI-TOF-Ms(matrix-assisted laser desorption time-of-flight mass) spectroscopy, Elemental Analysis, 1H NMR spectroscopy.