Synthesis of symmetrical and unsymmetrical subphthalocyanine dimers containing a hydroquinone bridge

Abstract

Three novel hydroquinone-based symmetrically and unsymmetrically substituted subphthalocyanine (SubPc) dimers have been synthesized through the axial substitution of the macrocycle. The mono SubPc hydroquinone derivative (Hq-SubPc) first prepared acts as a nucleophile which replaces the chlorine atom of the second SubPc molecule to form the dimer. The dimers were obtained by reacting hydroquinone and the respective SubPcs in a 1:1 molar ratio in toluene at 180 °C in a pressure vessel. This new approach allowed stoichiometric quantities of reactants to be utilized. All dimers were characterized by 1 H NMR, 13 C NMR, UV-vis, fluorescence and mass spectral analysis.