Issue 3, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
26 ربيع الأول 1439
Accepted
24 ربيع الثاني 1439
First published
28 ربيع الثاني 1439

Mater. Chem. Front., 2018,2, 585-590

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, 2, 585 DOI: 10.1039/C7QM00581D

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