A novel isoindole-containing polyaromatic hydrocarbon unexpectedly formed during the synthesis of meso-2,6-dichlorophenyl-substituted tribenzosubporphyrin

Yuta Shiina, Hideaki Karasaki, Shigeki Mori, Nagao Kobayashi, Hiroyuki Furuta, Soji Shimizu

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Abstract

A novel isoindole-containing polyaromatic hydrocarbon was unexpectedly formed during the synthesis of meso-2,6-dichlorophenyl-substituted tribenzosubporphyrin from a reaction of phthalimide and 2,6-dichlorophenylacetic acid in the presence of boric acid. Due to the highly annulated structure, this molecule exhibited blue color in solution, which was theoretically well reproduced by the HOMO-LUMO transitions based on the time-dependent DFT calculation. In this manuscript, the synthesis and properties of this polyaromatic hydrocarbon and meso-2,6-dichlorophenyl-substituted tribenzosubporphyrin are reported.

Original languageEnglish
Pages (from-to)1049-1054
Number of pages6
JournalJournal of Porphyrins and Phthalocyanines
Volume20
Issue number8-11
DOIs
Publication statusPublished - Aug 1 2016

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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