Journal
SYNLETT
Volume 34, Issue 12, Pages 1433-1436Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-2009-8219
Keywords
cycloparaphenylenes; cyclonaphthylenes; molecular nanocarbons; carbon nanobelts; methylene-bridged nanobelts; prism[6]arenes
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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).
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).
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