Chemistry Reference
In-Depth Information
Synthesis, Structures, and Physical
Properties of Aromatic Molecular-Bowl
Hydrocarbons
Yao-Ting Wu and Jay S. Siegel
Abstract This chapter summarizes the synthesis, physical properties, structure,
and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of
polynuclear aromatic compounds between the closed-shell fullerenes and the flat
extended arrays of graphene. These warped sheets can be seen as fragments of
fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature
endows them with physical properties distinct from flat polynuclear hydrocarbons,
which opens up unique possibilities for molecular bowls in various organic mate-
rials applications.
Keywords Buckybowl
Carbon nanotube
Corannulene
Sumanene
Contents
1 Introduction . . ................................................................................. 64
2 Corannulene and Its Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65
2.1 Corannulene and Simple Corannulene Derivatives ................................... 65
2.2 Highly Substituted Corannulenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
2.3 Cyclopentacorannulene, Acecorannulene and Annelated Corannulenes ............. 85
2.4 Benzocorannulene Family .............................................................. 88
2.5 Indenocorannulene Family . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91
2.6 Other Corannulene Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
2.7 The Correlations Between Structures and Bowl-to-Bowl Inversion Barriers . . . . . . . . 96
