Synthesis and Properties of Functionalized Buckybowls

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Synthetic methods for various type of functionalized buckybowls has been developed including C3 symmetric and unsymmetrical sumanenes, C2 symmetric corannulene derivatives, and fluorinated buckybowls.The thus-prepared functionalized buckybowls exhibit unique properties. In particular, crystals having columnar stacking structure shows high electron mobility even in the case of corannulene derivatives, which does not usually shows the electron mobility.The first example of the through-bond stereoelectronic effect of curved aromatic compounds was found in buckybowls, benzylic substituted sumanenes. Methyl- and hydroxyl-sumanene favour the endo-R conformer due to the different strength of hyperconjugation of the benzylic C-H bond and the bowl between the endo-R and exo-R conformers.