Phthalocyanines and Related Compounds:XLIII.Synthesis of Poly[phenyl(alkyl)sulfanyl]-Substituted Phthalonitriles and Some Phthalocyanines Based Thereon

摘要

Nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by benzene-and alkane-thiols in the presence of a base was studied at different reactant ratios.The substitution is characterized by complete regioselectivity:the chlorine atom in position 4 of tetrachlorophthalonitrile is replaced first;next follows replacement of the 5-chlorine atom.The reactions of tetrachlorophthalonitrile with nucleophiles at ratios of 1:2 and 1:4 lead to the formation of the corresponding 3,6-dichloro-4,5-bis[phenyl(alkyl)sulfanyl]-and tetrakis[phenyl(alkyl)sulfanyl]phthalonitriles.The latter were converted into metal complexes of[phenyl-(alkyl)sulfanyl]-substituted phthalocyanines which absorb in the red and near-IR regions of the electronic spectra.