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CC BY 4.0 · Synlett 2024; 35(15): 1739-1744
DOI: 10.1055/a-2223-7245
DOI: 10.1055/a-2223-7245
synpacts
Topological Bistability of the π-System in a Helicene Carbon Nanohoop
Funding for this work was provided by the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (Grant Agreement No. 949397).
Abstract
Molecules with a π-system that can be mapped onto a Möbius strip may display Möbius aromaticity. Such molecules are difficult to synthesize because they have a twisted structure. Recently, we combined chiral [6]helicene and fluorescent [7]cycloparaphenylene, and synthesized the first helicene para-phenylene ([6,7]HPP) carbon nanohoop. We have demonstrated that this design strategy ultimately provides a Möbius topology of the molecular π-electron system and, therefore, offers the potential to study Möbius aromaticity experimentally. In addition, the synthesized nanohoop exists as a mixture of conformers in solution. Some of the conformers possess a different orientability of their π-systems, i.e., they differ in their topology. As a result, the recorded circularly polarized luminescence of isolated enantiomers displays both left- and right-handedness of the emitted light, each emanating from a conformer with a different π-system topology. Therefore, [6,7]HPP provided the first experimental evidence of such topological bistability in carbon nanohoops.
Key words
circularly polarized luminescence - Möbius aromaticity - molecular topology - carbon nanohoops - cycloparaphenylenes - helicenesPublication History
Received: 28 November 2023
Accepted: 06 December 2023
Accepted Manuscript online:
06 December 2023
Article published online:
17 January 2024
© 2024. The Authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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