Issue 10, 2020

Folding of fluorinated oligoarylenes into non-alternant PAHs with various topological shapes

Abstract

An unprecedented [6]helicene's cavity closure indicating the possibility of introducing seven-membered rings via alumina-mediated C–F activation is shown. This finding, in combination with a directed quadruple annulation of fluorinated oligoarylenes, opens a short pathway to elusive non-alternant PAHs. Starting with one fluorinated block, we have synthesized through a two-step procedure three new representatives with helical-, bowl- and saddle-shapes. Additionally, the structure–property relationship in these new PAHs is explored via theoretical, optical, and X-ray crystallographic studies.

Graphical abstract: Folding of fluorinated oligoarylenes into non-alternant PAHs with various topological shapes

Supplementary files

Article information

Article type
Research Article
Submitted
25 Mar 2020
Accepted
07 Apr 2020
First published
17 Apr 2020

Org. Chem. Front., 2020,7, 1271-1275

Folding of fluorinated oligoarylenes into non-alternant PAHs with various topological shapes

V. Akhmetov, A. Förtsch, M. Feofanov, S. Troyanov and K. Amsharov, Org. Chem. Front., 2020, 7, 1271 DOI: 10.1039/D0QO00370K

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