TY - JOUR
T1 - Unexpected formation of a triphyrin in the reaction of dibromodipyrromethene and N,N-dimethylaminoethanol
AU - Shimizu, Soji
AU - Hirokawa, Shoma
AU - Kobayashi, Nagao
N1 - Funding Information:
This work was partly supported by a Grant-in-Aid for Young Scientists A (No. 26708003) from Japan Society for the Promotion of Science (JSPS), and a Grant-in-Aid for Scientific Research on Innovative Area, “New Polymeric Materials Based on Element-Blocks (No. 25102503), from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT). The authors thank Prof. Takeaki Iwamoto and Dr. Shintaro Ishida, Tohoku University for the X-ray measurement.
Publisher Copyright:
Copyright © 2014 World Scientific Publishing Company.
PY - 2014/8/1
Y1 - 2014/8/1
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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U2 - 10.1142/S1088424614500527
DO - 10.1142/S1088424614500527
M3 - Article
AN - SCOPUS:84908695187
SN - 1088-4246
VL - 18
SP - 721
EP - 726
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
ER -