Organic Chemistry Laboratory, Nagoya University

Synthesis and Properties of Methylene-bridged [6]Cyclo-2,6-naphthylene

Nobushige Kai, Hideya Kono, Akiko Yagi, Kenichiro Itami, Synlett 2022, accepted. DOI: 10.1055/a-2009-8219

The synthesis of a novel structurally constrained nanobelt, methylene-bridged [6]cyclo-2,6-naphthylene ([6]MCN), has been achieved by nickel-mediated intramolecular aryl–aryl coupling of triflated prism[6]arene. The structural and electronic properties of [6]MCN were revealed through NMR study and photophysical measurements. In contrast to methylene-bridged [6]cycloparaphenylene ([6]MCPP), our previously synthesized benzene-based analogue, [6]MCN has low strain energy (77.4 kcal·mol–1) and bright fluorescence (Φ = 0.20)