The Structure of Hexabenzotriphenylene and the Problem of
Overcrowded “<i>D</i><sub>3</sub><i><sub>h</sub></i>” Polycyclic Aromatic Compounds
Lisa Barnett
Douglas M. Ho
Kim K. Baldridge
Robert A. Pascal
10.1021/ja983471i.s001
https://acs.figshare.com/articles/dataset/The_Structure_of_Hexabenzotriphenylene_and_the_Problem_of_Overcrowded_i_D_i_sub_3_sub_i_sub_h_sub_i_Polycyclic_Aromatic_Compounds/3673008
Hexabenzotriphenylene (<b>1</b>, dibenzo[<i>f,j</i>]phenanthro[9,10-<i>s</i>]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 <b>1</b> is a strongly twisted, <i>D</i><sub>3</sub>-symmetric molecular propeller, in contrast to other highly substituted
triphenylenes (perfluoro- and perchlorotriphenylene) which adopt <i>C</i><sub>2</sub>-symmetric conformations. Computational
studies of these and other overcrowded, nominally <i>D</i><sub>3</sub><i><sub>h</sub></i>-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.
1999-01-14 00:00:00
origin
Compound 1
C 2
compound
Aromatic
phenanthro
triphenylene
D 3 h
Hexabenzotriphenylene
picene
Polycyclic
Overcrowded
perfluoro
Computational studies
vacuum pyrolysis
anhydride
phenanthrene
conformation
polycyclic
adequacy
dibenzo
propeller
Problem
method
D 3
contrast
perchlorotriphenylene
preference