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

doi:10.1002/anie.201101864

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 journal › Article › peer-review

78 Scopus citations

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 language	English
Pages (from-to)	5691-5694
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	25
DOIs	https://doi.org/10.1002/anie.201101864
State	Published - 14 Jun 2011

Keywords

annulation
aromaticity
carbazoles
porphyrinoids

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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.",

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author = "Chihiro Maeda and Tomoki Yoneda and Naoki Aratani and Yoon, {Min Chul} and Lim, {Jong Min} and Dongho Kim and Naoki Yoshioka and Atsuhiro Osuka",

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AU - Maeda, Chihiro

AU - Yoneda, Tomoki

AU - Aratani, Naoki

AU - Yoon, Min Chul

AU - Lim, Jong Min

AU - Kim, Dongho

AU - Yoshioka, Naoki

AU - Osuka, Atsuhiro

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AB - 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.

KW - annulation

KW - aromaticity

KW - carbazoles

KW - porphyrinoids

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JO - Angewandte Chemie - International Edition

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Synthesis of carbazole-containing porphyrinoids by a multiple annulation strategy: A core-modified and π-expanded porphyrin

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