Synthesis and Chiral Resolution of Twisted Carbon Nanobelts

Twisted carbon nanobelts could display persistent chirality, which is desirable for material applications, but their synthesis is very challenging. Herein, we report the successful synthesis and chiral resolution of such a kind of molecules (1-H and 1) with a figure-eight configuration. 1-H was synthesized first by macrocyclization through Suzuki coupling reaction followed by benzannulation via Bi(OTf)(3)-mediated cyclization reaction of vinyl ether. Oxidative dehydrogenation of 1-H gave the fully pi-conjugated 1. Their twisted structures were confirmed by X-ray crystallographic analysis and calculations, and they can be resolved by chiral high-performance liquid chromatography. The isolated enantiomers showed persistent chiroptical properties according to the circular dichroism measurements, with moderate vertical bar g(abs)vertical bar values (0.0016 for 1-H and 0.005-0.007 for 1). Their photophysical properties were also briefly studied.