Novel nonmetalated hydrophobic and metalated phthalocyanines bearing pyridine-2-thiol and 2,4,6-trimethylphenylamine substituents: Synthesis, spectroscopic, aggregation and thermal properties

Abstract

Novel metal-free and metallo-phthalocyanines, with different substituents at peripheral positions, have been synthesised by cyclotetramerisation of 4-(2,4,6-trimethylphenylamino)phthalonitrile and 4-(pyridine-2-ylsulfanyl)phthalonitrile in the presence of the corresponding divalent metal salts [Zn(II), Cu(II), Co(II) and Ni(II)]. Quaternisation of the metallophthalocyanine functionality produced quaternised cationic Zn, Cu, Ni and Co phthalocyanines, which are soluble in DMF, H2O and DMSO. The aggregation behaviour of these compounds was investigated in different concentrations of DMSO. Their thermal stability and electronic stability are reported.