Synthesis and Properties of Functionalized Buckybowls

研究了C3对称和不对称苏曼烯、C2对称角轮烯衍生物和含氟巴基碗的合成方法，合成的巴基碗具有独特的性能。 特别是，具有柱状堆叠结构的晶体显示出高的电子迁移率，即使在corannulene衍生物的情况下，这通常不显示电子mobility.The第一个例子的通过键立体电子效应的弯曲的芳香族化合物被发现在buckybowls，苄基取代的sumanenes。甲基-和羟基-苏曼烯有利于endo-R构象，由于不同强度的超共轭的苄基C-H键和碗之间的endo-R和exo-R构象。

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.