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Perylene diimide triple helix formation in the solid-state

Haddow, Sarah L.; Ring, David J.; Bagha, Hena; Pearce, Nicholas; Nowell, Harriet; Blake, Alexander J.; Lewis, William; McMaster, Jonathan; Champness, Neil R.

Authors

Sarah L. Haddow

David J. Ring

Hena Bagha

Nicholas Pearce

Harriet Nowell

Alexander J. Blake

William Lewis

Neil R. Champness



Abstract

The structural characterisation 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.

Citation

Haddow, S. L., Ring, D. J., Bagha, H., Pearce, N., Nowell, H., Blake, A. J., …Champness, N. R. (2018). Perylene diimide triple helix formation in the solid-state. Crystal Growth and Design, 18(2), https://doi.org/10.1021/acs.cgd.7b01268

Journal Article Type Article
Acceptance Date Dec 17, 2017
Online Publication Date Jan 8, 2018
Publication Date Feb 20, 2018
Deposit Date Feb 26, 2018
Publicly Available Date Mar 28, 2024
Journal Crystal Growth and Design
Print ISSN 1528-7483
Electronic ISSN 1528-7483
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 18
Issue 2
DOI https://doi.org/10.1021/acs.cgd.7b01268
Public URL https://nottingham-repository.worktribe.com/output/912433
Publisher URL https://pubs.acs.org/doi/abs/10.1021/acs.cgd.7b01268