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.

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., Lewis, W., McMaster, 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
• Journal: Crystal Growth and Design
• Print ISSN: 1528-7483
• Electronic ISSN: 1528-7505
• 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
• Contract Date: Feb 26, 2018