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The Structure of Hexabenzotriphenylene and the Problem of Overcrowded “D3h” Polycyclic Aromatic Compounds

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journal contribution
posted on 14.01.1999 by Lisa Barnett, Douglas M. Ho, Kim K. Baldridge, Robert A. Pascal
Hexabenzotriphenylene (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.

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