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Figure-of-Eight Helicene Carbon Nanohoop with Möbius Topology
preprintsubmitted 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 helicene into cycloparaphenylene. The stereogenic 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 metacycloparaphenylene, 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.