10.1021/ja983471i.s001
Lisa Barnett
Lisa
Barnett
Douglas M. Ho
Douglas M.
Ho
Kim K. Baldridge
Kim K.
Baldridge
Robert A. Pascal
Robert A.
Pascal
The Structure of Hexabenzotriphenylene and the Problem of
Overcrowded “<i>D</i><sub>3</sub><i><sub>h</sub></i>” Polycyclic Aromatic Compounds
American Chemical Society
1999
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
1999-01-14 00:00:00
Dataset
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.