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

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

Automated summary

A novel structurally constrained nanobelt, methylene bridged [6]cyclo-2,6-naphthylene ([6]MCN), was synthesized via the nickel-mediated intramolecular aryl-aryl coupling of a triflated prism[6]arene. The structural and electronic properties of [6]MCN were characterized using NMR studies and photophysical measurements. In contrast to methylene-bridged [6]cycloparaphenylene, our previously synthesized benzene-based analogue, [6]MCN exhibited low strain energy (77.4 kcalmiddotmol(-1)) and bright fluorescence (Phi = 0.20).