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Malinčík_2021_ChemRxiv_Figure-of-Eight Helicene Carbon Nanohoop with Möbius Topology.pdf (12.39 MB)

Figure-of-Eight Helicene Carbon Nanohoop with Möbius Topology

preprint
submitted on 09.02.2021, 19:09 and posted on 10.02.2021, 12:25 by Juraj Malinčík, Sudhakar Gaikwad, Marc-Aurèle Boillat, Daniel Häussinger, Tomas Solomek
We present design and synthesis of a new class of chiral figure-of-eight carbon nanohoops by integrating [6]helicene into [7]cycloparaphenylene. The stereogenic [6]helicene unit endows the helicene carbon nanohoop with chiroptical properties and configurational stability typical for higher helicenes, while the presence of radially conjugated oligo-p-phenylene moiety provides the optoelectronic properties similar to meta[8]cycloparaphenylene, such as emission of visible light with a high quantum yield. We discovered that the synthesized helicene carbon nanohoop possesses a Mobius topology in solution and confirmed this hypothesis by variable-temperature 1H NMR spectroscopy and DFT calculations. Our results suggest that a single helicene stereogenic unit and high molecular strain are sufficient to induce Mobius topology in molecular nanocarbon systems.

Funding

Swiss National Science Foundation, PZ00P2_174175

Swiss National Science Foundation, CRSK-2_190341

History

Email Address of Submitting Author

tomas.solomek@unibas.ch

Institution

University of Basel

Country

Switzerland

ORCID For Submitting Author

0000-0003-0013-4116

Declaration of Conflict of Interest

No conflict of interest.

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