Synthesis, structure, and chemical property of the first fluorine-containing porphycene

Takashi Hayashi, Yuji Nakashima, Kazuyuki Ito, Takahiro Ikegami, Isao Aritome, Akihiro Suzuki, Yoshio Hisaeda

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48 Citations (Scopus)

Abstract

(Matrix presented) A pyrrolic macrocycle, β -tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF3 substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the β-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.

Original languageEnglish
Pages (from-to)2845-2848
Number of pages4
JournalOrganic Letters
Volume5
Issue number16
DOIs
Publication statusPublished - Aug 7 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Hayashi, T., Nakashima, Y., Ito, K., Ikegami, T., Aritome, I., Suzuki, A., & Hisaeda, Y. (2003). Synthesis, structure, and chemical property of the first fluorine-containing porphycene. Organic Letters, 5(16), 2845-2848. https://doi.org/10.1021/ol0348452