Octakis(alkylthio)-substituted phthalocyanines and their interactions with silver(I) and palladium(II) ions

Abstract

Metal-free phthalocyanines and metal phthalocyaninates (M = Ni, Cu, Co or Zn) carrying eight alkylthio-groups on peripheral positions have been synthesised from 4,5-bis(alkylthio)phthalonitrile and 1,8-diazabicyclo[5.4.0]undec-7-ene (dbu) or the corresponding anhydrous metal salt [NiCl₂, CuCl, CoCl₂ or Zn(O₂CMe)₂]. The resulting compounds reacted with silver(I) or palladium(II) salts to form complexes with a phthalocyanine:metal ratio of 1 : 4. Spectrophotochemical investigation of these reactions revealed that complexation with Ag^I results in aggregation, while the addition of Pd^II destroys the aggregation and yields a new Q band at 720 nm.