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

A. G. GÜREK

Department of Chemistry, TÜBTAK, Marmara Research Center, P.O. Box 21 41470 Gebze, Kocaeli, Turkey

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and

Ö. BEKARO ĞLU

Department of Chemistry, Technical University of İstanbul, 80636 Maslak, İstanbul, Turkey

Corresponding author, Department of Chemistry, Technical University of İstanbul, 80636 Maslak, İstanbul, Turkey.

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https://doi.org/10.1002/(SICI)1099-1409(199707)1:3<227::AID-JPP17>3.0.CO;2-KCited by:43 (Source: Crossref)

Abstract

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, ¹H NMR and ¹³C 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 NOBF₄ increases the d.c. conductivity of 10 by a factor of four.

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