Synthesis of carbazole-based selenaporphyrin via annulation

Motoki Masuda, Chihiro Maeda, Naoki Yoshioka

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.

Original languageEnglish
Pages (from-to)578-581
Number of pages4
JournalOrganic Letters
Volume15
Issue number3
DOIs
Publication statusPublished - 2013 Feb 1

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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