ja983471i_si_001.cif (46.55 kB)
The Structure of Hexabenzotriphenylene and the Problem of Overcrowded “D3h” Polycyclic Aromatic Compounds
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posted on 1999-01-14, 00:00 authored by Lisa Barnett, Douglas M. Ho, Kim K. Baldridge, Robert A. PascalHexabenzotriphenylene (1, dibenzo[f,j]phenanthro[9,10-s]picene) has been prepared in 5% yield by
vacuum pyrolysis of phenanthrene-9,10-dicarboxylic anhydride, and its X-ray structure has been determined.
Compound 1 is a strongly twisted, D3-symmetric molecular propeller, in contrast to other highly substituted
triphenylenes (perfluoro- and perchlorotriphenylene) which adopt C2-symmetric conformations. Computational
studies of these and other overcrowded, nominally D3h-symmetric, polycyclic aromatic compounds are reported,
and the origins of their conformational preferences and the adequacy of various computational methods for
treating these compounds are discussed.