Perylene Diimide Triple Helix Formation in the Solid State
The 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 t...
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Veröffentlicht in: | Crystal growth & design 2018-02, Vol.18 (2), p.802-807 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | The 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. |
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ISSN: | 1528-7483 1528-7505 |
DOI: | 10.1021/acs.cgd.7b01268 |