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

Soji Shimizu, Shoma Hirokawa, Nagao Kobayashi

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)721-726
Number of pages6
JournalJournal of Porphyrins and Phthalocyanines
Publication statusPublished - 2014 Aug 1


  • Contracted porphyrin analog
  • Thermal conformational equilibrium
  • Triphyrin
  • UV-vis absorption

ASJC Scopus subject areas

  • Chemistry(all)


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