Synthesis and properties of porphyrazines containing long alkyl groups

Abstract

Substituted phthalocyanines have attracted much attention due to their potential application in modern material technologies because of their peculiar optic, liquid crystalline, semi-conducting properties1. Strongly electron donating linear long alkyl groups have a large influence on the ?-system of phthalocyanine macrocycle and its spectral, and coordination properties. The phthalocyanines soluble in organic solvents have been developed by peripheral introduction of substituents groups. We have reported a new method for preparation of the new types of tetrapyrazinoporphyrazines synthesized by substituting tert-butyl benzene and linear long alkyl groups of the 2,3-position of dicyanopyrazines. A fridel-craft acylation and a reduction of an acetate group to the hydroxyl group were used to prepare the precursor of dicyanopyrazines. And these dicyanopyrazines were easily tetramerized to porphyrazines in the Magnesium butoxide solution, and were demetallized in acidic condition. Therefore, Compared with the usual phthalocyanine, phthalocyanines substituted with tert-butylbenzene and linear long alkyl groups showed specific properties. The synthetic availability of tetrapyrazinoporphyrazine in a wide range of sizes makes them attractive molecular components for the construction of electronic and photonic nano-devices and smart nano-materials. The synthesized tetrapyrazinoporphyrazine metal complexes were characterized by UV-visible spectroscopy, MALDI-TOF-Ms (matrix-assisted laser desorption ionization time-of-flight mass) spectroscopy, elemental analysis and 1H NMR spectroscopy.