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Perylene Diimide Triple Helix Formation in the Solid State

DOI: 10.1021/acs.cgd.7b01268 DOI Help

Authors: Sarah L. Haddow (University of Nottingham) , David J. Ring (University of Nottingham) , Hena Bagha (University of Nottingham) , Nicholas Pearce (University of Nottingham) , Harriet Nowell (Diamond Light Source) , Alexander J. Blake (University of Nottingham) , William Lewis (University of Nottingham) , Jonathan Mcmaster (University of Nottingham) , Neil R. Champness (University of Nottingham)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Crystal Growth & Design

State: Published (Approved)
Published: January 2018
Diamond Proposal Number(s): 8618

Abstract: 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.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction