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

51 Citations (Scopus)

Abstract

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
Volume50
Issue number25
DOIs
Publication statusPublished - 2011 Jun 14

Fingerprint

Porphyrins
Thiophene
Thiophenes
Dimers
Absorption spectra
Amines
Copper
carbazole

Keywords

  • annulation
  • aromaticity
  • carbazoles
  • porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Synthesis of carbazole-containing porphyrinoids by a multiple annulation strategy : A core-modified and π-expanded porphyrin. / Maeda, Chihiro; Yoneda, Tomoki; Aratani, Naoki; Yoon, Min Chul; Lim, Jong Min; Kim, Dongho; Yoshioka, Naoki; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 50, No. 25, 14.06.2011, p. 5691-5694.

Research output: Contribution to journalArticle

Maeda, Chihiro ; Yoneda, Tomoki ; Aratani, Naoki ; Yoon, Min Chul ; Lim, Jong Min ; Kim, Dongho ; Yoshioka, Naoki ; Osuka, Atsuhiro. / Synthesis of carbazole-containing porphyrinoids by a multiple annulation strategy : A core-modified and π-expanded porphyrin. In: Angewandte Chemie - International Edition. 2011 ; Vol. 50, No. 25. pp. 5691-5694.
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