cg7b01268_si_001.pdf (659.93 kB)
Perylene Diimide Triple Helix Formation in the Solid State
journal contribution
posted on 2018-01-08, 19:54 authored by Sarah
L. Haddow, David J. Ring, Hena Bagha, Nicholas Pearce, Harriet Nowell, Alexander J. Blake, William Lewis, Jonathan McMaster, Neil R. ChampnessThe
structural characterization of single crystals of di-4-pyridyl-substituted
3,4,9,10-perylenetetracarboxylic diimide reveals a surprising triple
helical arrangement. The intermolecular interactions that lead to
such an arrangement are investigated by Hirshfeld surface analysis
and indicate that the supramolecular structure arises due to a combination
of C–H···O interactions and π–π
stacking interactions between adjacent perylene diimide (PDI) species.
The interplay of these interactions leads to the formation of a tubular
structure enclosed by the triple helix of PDI molecules. In contrast,
the analogous phenyl-substituted molecule forms a simple one-dimensional
stack of PDI molecules which is also unusual in that the perylene
core adopts an essentially planar arrangement despite bay substitution.