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Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes

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Abstract

The enantioselective synthesis of a phospha[9]helicene with a bibenzopicene skeleton has been achieved via the rhodium-mediated intermolecular [2+2+2] cycloaddition of a binaphthyl-linked tetrayne with a phosphorus-linked diyne. The photophysical and chiroptical properties of the thus obtained phospha[9]helicene were compared with our previously synthesized benzopicene-based carbo[9]helicene and triphenylene-based carbo- and phospha[7]helicenes. Significantly red shifted absorption and emission maxima were observed in the benzopicene-based phospha[9]helicene as a result of extended π-conjugation, but its fluorescence quantum yield and circularly polarized luminescence activity (glum) were lower than those of the other three helicenes.

Graphical abstract: Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes

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Publication details

The article was received on 14 Dec 2017, accepted on 11 Jan 2018 and first published on 15 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QM00581D
Citation: Mater. Chem. Front., 2018, Advance Article
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    Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes

    S. Nishigaki, K. Murayama, Y. Shibata and K. Tanaka, Mater. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QM00581D

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