Supramolecular layers and versatile packing modes: the solid state behavior of ortho, ortho-linked bisphenols

Augustin, Andre U. and Katzsch, Felix and Prior, Stephen H. and Gruber, Tobias (2017) Supramolecular layers and versatile packing modes: the solid state behavior of ortho, ortho-linked bisphenols. Journal of Molecular Structure, 1135 . pp. 153-165. ISSN 0022-2860

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Abstract

A series of ortho-ortho-linked bisphenols featuring electron-withdrawing groups (EWGs) attached to the phenolic rings is reported. Their respective molecular structures and packing behaviors have been studied by X-ray diffraction, comparatively discussed and put into relation with the unsubstituted mother compound. Except for the mother compound, the molecular structures of all bisphenols studied here exhibit distorted aromatic moieties. Hence, the substituents studied here prevent proximal positioning of phenolic units and the formation of strong O-H···O hydrogen bonds. In the packing of the underivatized bisphenol we found a strand-like molecular arrangement featuring strong O-H···O hydrogen bonds and extensive edge-to-face contacts (C-H···π) between the bisphenol molecules. The introduction of EWGs to the aromatic moieties changes these intermolecular interactions into face-to-face contacts resulting either in bisphenol stacks or handshake-like motifs between two bisphenol molecules. In both cases, the C-H···π interactions are more or less replaced by C-H···O contacts as the prevalent non-covalent interaction. In the packing of two nitro bisphenols in their DMSO inclusion compounds an exciting layered arrangement is observed, which also matches with the pronounced foliated habitus of their crystals. Additionally, proton NMR was used to establish the binding coefficients between the respective bisphenols and DMSO in solution.

Keywords:bisphenols, layered material, materials chemistry, X-ray diffraction
Subjects:F Physical Sciences > F200 Materials Science
F Physical Sciences > F131 Crystallography
F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
College of Science > School of Pharmacy
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ID Code:25846
Deposited On:24 Jan 2017 08:52

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