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
Hauptverfasser: Haddow, Sarah L, Ring, David J, Bagha, Hena, Pearce, Nicholas, Nowell, Harriet, Blake, Alexander J, Lewis, William, McMaster, Jonathan, Champness, Neil R
Format: Artikel
Sprache:eng
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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.
ISSN:1528-7483
1528-7505
DOI:10.1021/acs.cgd.7b01268