A new unsymmetrical phthalocyanine with a single o-carborane substituent


Ozgur N., NAR I., Gül A., HAMURYUDAN E.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.781, pp.53-58, 2015 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 781
  • Publication Date: 2015
  • Doi Number: 10.1016/j.jorganchem.2015.01.011
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.53-58

Abstract

Unsymmetrical zinc phthalocyanine carrying a single o-carborane substituent on the peripheral position was synthesized in a multistep reaction sequence. At the first step, metal-free phthalocyanine 3 was prepared by cyclotetramerization of 4,5-di(hexylthio) phthalonitrile and 4-(2-hydroxyethylthio) phthalonitrile in pentanol in the presence of lithium; and zinc phthalocyanine 4 was prepared by insertion of Zn(II) salt. After esterification of phthalocyanine 4 with 4-pentynoic acid, terminal alkynyl bearing precursor phthalocyanine 5 was obtained. At the last step, reaction of decaborane with phthalocyanine 5 yielded phthalocyanine 6 with the desired o-carborane moiety. The new phthalocyanine compounds were characterized by elemental analysis, NMR, FT-IR, UV-vis and mass spectral data. Aggregation behaviour and electrochemical properties of these newly synthesized unsymmetrical phthalocyanine derivatives were also reported. (C) 2015 Elsevier B.V. All rights reserved.