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, 1 H NMR and
13 C NMR spectroscopy. The electrical conductivity
measurements of three of the four network polymers were unsuccessful;
however chemical doping with NOBF 4 could be increased
to a measurable value. The electrical conductivity of the dimeric
phthalocyanines are in the semiconductor range.
1,4,7,10-Tetrathia (12-crown-4)-bridged new polymeric phthalocyanines 9 and 10 have been synthesized by the reaction of tetracyanodibenzo[1,4,7,10-tetrathia (12-crown-4)] in the presence of a strong organic base or Zn ( OAc )2 respectively. Furthermore, 1,4,7,10-tetrathia (12-crown-4)-linked peripherally octa-substituted dimeric phthalocyanine 12, which contains a combination of hexakis(alkylthia) side chains was synthesized by the reaction of subphthalocyanine 11 with the iminoisoindoline derivative 8. The new compounds have been characterized by elemental analyses, IR, UV/vis, mass, 1 H NMR and 13 C NMR spectroscopy. The thermal stabilities of the compounds were determined by thermogravimetric analysis. The electrical conductivity of the polymeric, 9 and 10, and dimeric phthalocyanines, 12 and 13, are in the semiconductor range; chemical doping with NOBF 4 increases the d.c. conductivity of 10 by a factor of four.
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