Synthesis of carbazole-based hetero-core-modified porphyrins

Chihiro Maeda, Motoki Masuda, Naoki Yoshioka

Research output: Contribution to journalArticle

11 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

Fingerprint

hydrazine
carbazoles
Porphyrins
porphyrins
Thiophenes
hydrazines
synthesis
Selenium
thiophenes
selenium
Discrete Fourier transforms
Dimers
Amines
Charge transfer
amines
dimers
charge transfer
Nuclear magnetic resonance
Oxidation
nuclear magnetic resonance

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Synthesis of carbazole-based hetero-core-modified porphyrins. / Maeda, Chihiro; Masuda, Motoki; Yoshioka, Naoki.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 17, 07.05.2014, p. 2656-2662.

Research output: Contribution to journalArticle

Maeda, Chihiro ; Masuda, Motoki ; Yoshioka, Naoki. / Synthesis of carbazole-based hetero-core-modified porphyrins. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 17. pp. 2656-2662.
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