Intramolecular Electronic Coupling in the Thiophene-Bridged Carbazole-Based Diporphyrin

Chihiro Maeda; Mototsugu Takata; Asami Honsho; Tadashi Ema

doi:10.1021/acs.orglett.6b03054

Intramolecular Electronic Coupling in the Thiophene-Bridged Carbazole-Based Diporphyrin

Chihiro Maeda, Mototsugu Takata, Asami Honsho, Tadashi Ema

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

The Glaser coupling reaction of ethynyl-substituted carbazole-based isophlorins provided butadiyne-bridged dimers, which were transformed into the thiophene-bridged dimers via the annulation reaction. Oxidation of these isophlorin dimers afforded carbazole-based diporphyrins. Notable electronic interactions in the diporphyrins have been confirmed by means of UV/vis-near-infrared (NIR) absorption spectroscopy, cyclic voltammetry (CV) measurements, and density functional theory (DFT) calculations.

Original language	English
Pages (from-to)	6070-6073
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.6b03054
Publication status	Published - Dec 2 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The Glaser coupling reaction of ethynyl-substituted carbazole-based isophlorins provided butadiyne-bridged dimers, which were transformed into the thiophene-bridged dimers via the annulation reaction. Oxidation of these isophlorin dimers afforded carbazole-based diporphyrins. Notable electronic interactions in the diporphyrins have been confirmed by means of UV/vis-near-infrared (NIR) absorption spectroscopy, cyclic voltammetry (CV) measurements, and density functional theory (DFT) calculations.",

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AB - The Glaser coupling reaction of ethynyl-substituted carbazole-based isophlorins provided butadiyne-bridged dimers, which were transformed into the thiophene-bridged dimers via the annulation reaction. Oxidation of these isophlorin dimers afforded carbazole-based diporphyrins. Notable electronic interactions in the diporphyrins have been confirmed by means of UV/vis-near-infrared (NIR) absorption spectroscopy, cyclic voltammetry (CV) measurements, and density functional theory (DFT) calculations.

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Intramolecular Electronic Coupling in the Thiophene-Bridged Carbazole-Based Diporphyrin

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