Synthesis of carbazole-based hetero-core-modified porphyrins

Chihiro Maeda, Motoki Masuda, Naoki Yoshioka

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Cu(i)-mediated annulation reaction of a 1,1′-(1,3-butadiyne)-8, 8′-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a-11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-core-modified isophlorine 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13, which exhibited NIR absorption. The intramolecular charge transfer from Se to S was confirmed by the 1H NMR results along with DFT calculations. This journal is

Original languageEnglish
Pages (from-to)2656-2662
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number17
DOIs
Publication statusPublished - 2014 May 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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