Synthesis of a Möbius carbon nanobelt

Abstract

Technologies for the creation of topological carbon nanostructures have greatly advanced synthetic organic chemistry and materials science. Although simple molecular nanocarbons with a belt topology have been constructed, analogous carbon nanobelts with a twist—more specifically, Möbius carbon nanobelts (MCNBs)—have not yet been synthesized owing to their high intrinsic strain. Here we report the synthesis, isolation and characterization of a MCNB. Calculations of strain energies suggest that large MCNBs are synthetically accessible. Designing a macrocyclic precursor with an odd number of repeat units led to a successful synthetic route via Z-selective Wittig reactions and nickel-mediated intramolecular homocoupling reactions, which yielded (25,25)MCNB over 14 steps. NMR spectroscopy and theoretical calculations reveal that the twist moiety of the Möbius band moves quickly around the MCNB molecule in solution. The topological chirality that originates from the Möbius structure was confirmed experimentally using chiral HPLC separation and circular dichroism spectroscopy. [Figure not available: see fulltext.]