Perylene diimide triple helix formation in the solid-state
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 t...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
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American Chemical Society
2018
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| Online Access: | https://eprints.nottingham.ac.uk/50018/ |
| _version_ | 1848798130458329088 |
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| author | Haddow, Sarah L. Ring, David J. Bagha, Hena Pearce, Nicholas Nowell, Harriet Blake, Alexander J. Lewis, William McMaster, Jonathan Champness, Neil R. |
| author_facet | Haddow, Sarah L. Ring, David J. Bagha, Hena Pearce, Nicholas Nowell, Harriet Blake, Alexander J. Lewis, William McMaster, Jonathan Champness, Neil R. |
| author_sort | Haddow, Sarah L. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:14:53Z |
| format | Article |
| id | nottingham-50018 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:14:53Z |
| publishDate | 2018 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-500182020-05-04T19:32:51Z https://eprints.nottingham.ac.uk/50018/ 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. 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. American Chemical Society 2018-02-20 Article PeerReviewed Haddow, Sarah L., Ring, David J., Bagha, Hena, Pearce, Nicholas, Nowell, Harriet, Blake, Alexander J., Lewis, William, McMaster, Jonathan and Champness, Neil R. (2018) Perylene diimide triple helix formation in the solid-state. Crystal Growth and Design, 18 (2). pp. 802-807. ISSN 1528-7483 https://pubs.acs.org/doi/abs/10.1021/acs.cgd.7b01268 doi:10.1021/acs.cgd.7b01268 doi:10.1021/acs.cgd.7b01268 |
| spellingShingle | Haddow, Sarah L. Ring, David J. Bagha, Hena Pearce, Nicholas Nowell, Harriet Blake, Alexander J. Lewis, William McMaster, Jonathan Champness, Neil R. Perylene diimide triple helix formation in the solid-state |
| title | Perylene diimide triple helix formation in the solid-state |
| title_full | Perylene diimide triple helix formation in the solid-state |
| title_fullStr | Perylene diimide triple helix formation in the solid-state |
| title_full_unstemmed | Perylene diimide triple helix formation in the solid-state |
| title_short | Perylene diimide triple helix formation in the solid-state |
| title_sort | perylene diimide triple helix formation in the solid-state |
| url | https://eprints.nottingham.ac.uk/50018/ https://eprints.nottingham.ac.uk/50018/ https://eprints.nottingham.ac.uk/50018/ |