10.1021/ja067571x.s010
Kenneth E. Maly
Kenneth E.
Maly
Eric Gagnon
Eric
Gagnon
Thierry Maris
Thierry
Maris
James D. Wuest
James D.
Wuest
Engineering Hydrogen-Bonded Molecular Crystals Built from
Derivatives of Hexaphenylbenzene and Related Compounds
American Chemical Society
2007
core
compound 4 crystallizes
molecule
hexaphenylbenzene
diaminotriazine groups
unsubstituted phenyl groups
Analogue
2007-04-11 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Engineering_Hydrogen_Bonded_Molecular_Crystals_Built_from_Derivatives_of_Hexaphenylbenzene_and_Related_Compounds/3013600
Hexakis[4-(2,4-diamino-1,3,5-triazin-6-yl)phenyl]benzene (<b>4</b>) incorporates a disc-shaped hexaphenylbenzene core and six peripheral diaminotriazine groups that can engage in hydrogen bonding according
to established motifs. Under all conditions examined, compound <b>4</b> crystallizes as planned to give closely
related noninterpenetrated three-dimensional networks built from sheets in which each molecule has six
hydrogen-bonded neighbors. In the structure of compound <b>4</b>, the number of hydrogen bonds per molecule
and the percentage of volume accessible to guests approach the highest values so far observed in molecular
networks. Analogue <b>5</b> (which has the same hexaphenylbenzene core but only four diaminotriazine groups
at the 1,2,4,5-positions) and analogue <b>7</b> (in which the two unsubstituted phenyl groups of compound <b>5</b> are
replaced by methyl groups) crystallize according to a closely similar pattern. Analogues with flatter
pentaphenylbenzene or tetraphenylbenzene cores crystallize differently, underscoring the importance of
maintaining a consistent molecular shape in attempts to engineer crystals with predetermined properties.