Ring-expanded porphyrins as an approach towards highly conductive molecular semiconductors

Nagao Kobayashi, W. Andrew Nevin, Satoshi Mizunuma, Hiroshi Awaji, Minori Yamaguchi

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62 Citations (Scopus)


As an approach to obtaining molecular semiconductors with high conductivity, it was attempted to lower the activation energy of conduction by enlarging the π-conjugated system in porphyrin materials. An anthraporphyrin (ZnTAnP) has been synthesized for the first time, and the spectroscopic, electrochemical and semiconductive properties have been characterized as a function of increasing molecular size, in the order: tetraphenylporphyrin (ZnTPP), tetrabenzoporphyrin (ZnTBP), tetranaphthaloporphyrin (ZnTNP), and ZnTAnP. With enlargement of the macrocycle, the Q band shifts to the red, and the absolute values of oxidation and reduction potentials become smaller. Room temperature conductivities of air-doped ZnTPP, ZnTBP, ZnTNP, and ZnTAnP thin films are < 10-11, 4 × 10-10, 3 × 10-4 and 1 × 10-7 Ω-1 cm-1, respectively. The smaller conductivity of ZnTAnP appears due to the formation of a stable charge transfer complex with oxygen.

Original languageEnglish
Pages (from-to)51-54
Number of pages4
JournalChemical Physics Letters
Issue number1
Publication statusPublished - 1993 Apr 2

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry


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