Synthesis of carbazole-based selenaporphyrin via annulation

Motoki Masuda, Chihiro Maeda, Naoki Yoshioka

Research output: Contribution to journalArticle

25 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

Fingerprint

carbazoles
Dimers
hydrazine
dimers
synthesis
furans
Cyclization
hydrazines
Selenium
selenium
Absorption spectra
absorption spectra
Oxidation
oxidation
acids
Acids
carbazole

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of carbazole-based selenaporphyrin via annulation. / Masuda, Motoki; Maeda, Chihiro; Yoshioka, Naoki.

In: Organic Letters, Vol. 15, No. 3, 01.02.2013, p. 578-581.

Research output: Contribution to journalArticle

Masuda, Motoki ; Maeda, Chihiro ; Yoshioka, Naoki. / Synthesis of carbazole-based selenaporphyrin via annulation. In: Organic Letters. 2013 ; Vol. 15, No. 3. pp. 578-581.
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