Synthesis of di-peri-dinaphthoporphyrins by PtCl2-mediated cyclization of quinodimethane-type porphyrins

Masataka Umetani, Koji Naoda, Takayuki Tanaka, Seung Kyu Lee, Juwon Oh, Dongho Kim, Atsuhiro Osuka

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7 Citations (Scopus)

Abstract

Di-peri-dinaphthoporphyrins can be regarded as a key and common substructure of fused porphyrinoids. PtCl2-mediated cycloisomerization reaction of quinodimethane-type porphyrins provided these doubly fused porphyrins, which exhibit characteristic paratropic ring currents that presumably arise from 24 π antiaromatic circuit as a dominant resonance contributor. UV/Vis absorption spectra, cyclic voltammetry, and excited-state dynamics as well as theoretical calculation support this conclusion. The core of the matter: Di-peri-dinaphthoporphyrins have been synthesized by PtCl2-mediated cycloisomerization reaction of quinodimethane-type porphyrins. These porphyrins can be regarded as a key substructure of fused porphyrinoids, for which a 24π antiaromatic circuit was proven to be a dominant resonance contributor by 1H NMR, UV/Vis absorption, cyclic voltammetry, NICS calculations, and AICD plot.

Original languageEnglish
Pages (from-to)6305-6309
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number21
DOIs
Publication statusPublished - 2016 May 17

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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