Dioxa-dithia Macrocycle-bridged Dimeric with Hexakis(alkylthio) Substituents and Network Polymer Phthalocyanines

1,7-dithia (12-crown-4)-bridged phthalocyanine network polymers were prepared from tetracyanodibenzo-[1,7-dithia(12-crown-4)]. In addition, the synthesis of two 1,7-dithia (12-crown-4) linked peripherally octa-substituted dimeric phthalocyanines, which contain a combination of hexakis(alkylthia) side chains, is described. These extremely soluble compounds were prepared by the condensation of an iminoisoindoline derivative and a subphthalocyanine. The novel compounds are characterized by elemental analyses, UV/vis, IR, mass, H-1 NMR and C-13 NMR spectroscopy. The electrical conductivity measurements of three of the four network polymers were unsuccessful; however chemical doping with NOBF4 could be increased to a measurable value. The electrical conductivity of the dimeric phthalocyanines are in the semiconductor range. (C) 1997 by John Wiley & Sons, Ltd.