Unexpected formation of a triphyrin in the reaction of dibromodipyrromethene and N,N-dimethylaminoethanol

Soji Shimizu, Shoma Hirokawa, Nagao Kobayashi

研究成果: ジャーナルへの寄稿記事

抄録

A novel triphyrin was unexpectedly formed as a major by-product in the synthesis of mesoaryl-substituted dibenzo-5,10,15-triazaporphyrin from meso-aryl-substituted 1,9-dibromodipyrromethene and 5,6-diaryl-substituted 1,3-diiminoisoindoline in the presence of N,N-dimethylaminoethanol (DMAE). X-ray single crystal diffraction analysis elucidated that the terminal α-positions of this triphyrin were bridged by an N-methylaminoethoxy chain, which plausibly originated from DMAE during the reaction. The same compound was also obtained as a major product in the reaction of DMAE and meso-arylsubstituted 1,9-dibromodipyrromethene. Its unique properties, such as conformational fexibility of the bridging moiety and broad absorption in the visible region, were also revealed by1H NMR and UV-vis absorption spectroscopies.

元の言語英語
ページ(範囲)721-726
ページ数6
ジャーナルJournal of Porphyrins and Phthalocyanines
18
DOI
出版物ステータス出版済み - 8 1 2014

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Deanol
Ultraviolet spectroscopy
Absorption spectroscopy
Byproducts
Diffraction
Nuclear magnetic resonance
Single crystals
X rays

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

これを引用

Unexpected formation of a triphyrin in the reaction of dibromodipyrromethene and N,N-dimethylaminoethanol. / Shimizu, Soji; Hirokawa, Shoma; Kobayashi, Nagao.

:: Journal of Porphyrins and Phthalocyanines, 巻 18, 01.08.2014, p. 721-726.

研究成果: ジャーナルへの寄稿記事

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abstract = "A novel triphyrin was unexpectedly formed as a major by-product in the synthesis of mesoaryl-substituted dibenzo-5,10,15-triazaporphyrin from meso-aryl-substituted 1,9-dibromodipyrromethene and 5,6-diaryl-substituted 1,3-diiminoisoindoline in the presence of N,N-dimethylaminoethanol (DMAE). X-ray single crystal diffraction analysis elucidated that the terminal α-positions of this triphyrin were bridged by an N-methylaminoethoxy chain, which plausibly originated from DMAE during the reaction. The same compound was also obtained as a major product in the reaction of DMAE and meso-arylsubstituted 1,9-dibromodipyrromethene. Its unique properties, such as conformational fexibility of the bridging moiety and broad absorption in the visible region, were also revealed by1H NMR and UV-vis absorption spectroscopies.",
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AU - Hirokawa, Shoma

AU - Kobayashi, Nagao

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N2 - A novel triphyrin was unexpectedly formed as a major by-product in the synthesis of mesoaryl-substituted dibenzo-5,10,15-triazaporphyrin from meso-aryl-substituted 1,9-dibromodipyrromethene and 5,6-diaryl-substituted 1,3-diiminoisoindoline in the presence of N,N-dimethylaminoethanol (DMAE). X-ray single crystal diffraction analysis elucidated that the terminal α-positions of this triphyrin were bridged by an N-methylaminoethoxy chain, which plausibly originated from DMAE during the reaction. The same compound was also obtained as a major product in the reaction of DMAE and meso-arylsubstituted 1,9-dibromodipyrromethene. Its unique properties, such as conformational fexibility of the bridging moiety and broad absorption in the visible region, were also revealed by1H NMR and UV-vis absorption spectroscopies.

AB - A novel triphyrin was unexpectedly formed as a major by-product in the synthesis of mesoaryl-substituted dibenzo-5,10,15-triazaporphyrin from meso-aryl-substituted 1,9-dibromodipyrromethene and 5,6-diaryl-substituted 1,3-diiminoisoindoline in the presence of N,N-dimethylaminoethanol (DMAE). X-ray single crystal diffraction analysis elucidated that the terminal α-positions of this triphyrin were bridged by an N-methylaminoethoxy chain, which plausibly originated from DMAE during the reaction. The same compound was also obtained as a major product in the reaction of DMAE and meso-arylsubstituted 1,9-dibromodipyrromethene. Its unique properties, such as conformational fexibility of the bridging moiety and broad absorption in the visible region, were also revealed by1H NMR and UV-vis absorption spectroscopies.

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