Synthesis of carbazole-containing porphyrinoids by a multiple annulation strategy: A core-modified and π-expanded porphyrin

Chihiro Maeda, Tomoki Yoneda, Naoki Aratani, Min Chul Yoon, Jong Min Lim, Dongho Kim, Naoki Yoshioka, Atsuhiro Osuka

Research output: Contribution to journalArticle

55 Citations (Scopus)


Going around in circles: The copper(I)-mediated annulation of a doubly 1,3-butadiyne-bridged carbazole dimer with amines or Na2S provides isophlorins containing carbazole or thiophene-carbazole moieties, respectively (see scheme). Oxidization of the thiophene-containing isophlorin with MnO 2 gives the corresponding porphyrin, which displays distinct aromaticity and remarkably intensified and red-shifted absorption bands in the near IR region.

Original languageEnglish
Pages (from-to)5691-5694
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number25
Publication statusPublished - Jun 14 2011
Externally publishedYes



  • annulation
  • aromaticity
  • carbazoles
  • porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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