Topological Bistability of the π-System in a Helicene Carbon Nanohoop

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 - helicenes

Publication History

Received: 28 November 2023

Accepted: 06 December 2023

Accepted Manuscript online:
06 December 2023

Article published online:
17 January 2024

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