2,3,9,10,16,17,23,24-Octakis(hexylsulfonyl)phthalocyanines with good n-type semiconducting properties. Synthesis, spectroscopic, and electrochemical characteristics

Yi Zhang, Pan Ma, Peihua Zhu, Xianyao Zhang, Yingning Gao, Dongdong Qi, Yongzhong Bian, Nagao Kobayashi, Jianzhuang Jiang

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The synthesis of peripherally octa-substituted phthalocyanine compounds with eight strong electron-withdrawing hexylsulfonyl groups was systematically studied. Three new phthalocyanines M[Pc(SO2C6H 13)8] [Pc(SO2C6H13) 8 = 2,3,9,10,16,17,23,24-octakis(hexylsulfonyl)phthalocyaninate; M = 2H (1), Cu (2), Zn (3)] were synthesized via direct cyclic tetramerization of 4,5-di(hexylsulfonyl)phthalonitrile or through a diiminoisoindoline intermediate. Compounds 1-3 could alternatively be prepared by oxidation of the hexylthio substituents in corresponding 2,3,9,10,16,17,23,24-octakis(hexylthio) phthalocyanine compounds M[Pc(SC6H13)8] (M = 2H, Cu, Zn) with m-chloroperbenzoic acid. They were fully characterized by elemental analysis and a series of spectroscopic methods. Their electrochemistry was studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Density function theory (DFT) calculations were conducted to study the effect of the strong electron-withdrawing groups on the electronic structure of the phthalocyanine molecules. Particularly, the first reduction potentials in the range -0.30∼-0.04 V vs. the saturated calomel electrode (SCE) for 1-3 reveal their n-type semiconducting nature. The current-voltage characteristics of their aggregates demonstrate the good semiconducting properties especially for 1 and 2 with the conductivity value of 5.24 × 10-4 and 2.73 × 10-4 S m-1, respectively.

Original languageEnglish
Pages (from-to)6515-6524
Number of pages10
JournalJournal of Materials Chemistry
Volume21
Issue number18
DOIs
Publication statusPublished - 2011 May 14

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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