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Synthesis, structure and binding properties of a series of dissymmetric resorcin[4]arene-based cavitands
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Knighton, Richard C. and Chaplin, Adrian B. (2017) Synthesis, structure and binding properties of a series of dissymmetric resorcin[4]arene-based cavitands. Tetrahedron, 73 (31). pp. 4591-4596. doi:10.1016/j.tet.2017.06.023 ISSN 0040-4020 .
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Official URL: http://dx.doi.org/10.1016/j.tet.2017.06.023
Abstract
The synthesis of four new dissymmetric cavitands is reported. These deep-walled receptors are constructed from a resorcin[4]arene scaffold bearing anti-disposed quinoxaline substituents, with either N-haloalkyl-diazaphthalimide (1), dinitrophenyl (2) or diaminophenyl (3) moieties as the other wall components. The structure and inclusion properties of 1 and 2 have been probed in solution by NMR spectroscopy and notably in the solid-state by X-ray crystallography. The diazaphthalimide-based compounds 1 crystallise as 1:1 host-guest complexes with chloroform, with the resorcin[4]arene scaffolds adopting pinched cone conformations. Conversely, the dinitrophenyl-variant 2 features a more open, symmetric structure in the solid-state and co-crystallises with two acetone molecules within the central cavity. Preliminary binding experiments in mesitylene-d12 at 303 K demonstrate 1 (Kapp = 5 × 102 M−1) and 2 (Kapp = 2 × 102 M−1) are effective hosts for cyclohexane guest molecules in the absence of competitive solvent inclusion.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Library of Congress Subject Headings (LCSH): | Supramolecular chemistry, Nuclear magnetic resonance spectroscopy, X-ray crystallography | ||||||||
Journal or Publication Title: | Tetrahedron | ||||||||
Publisher: | Pergamon | ||||||||
ISSN: | 0040-4020 | ||||||||
Official Date: | 3 August 2017 | ||||||||
Dates: |
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Volume: | 73 | ||||||||
Number: | 31 | ||||||||
Page Range: | pp. 4591-4596 | ||||||||
DOI: | 10.1016/j.tet.2017.06.023 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 15 August 2017 | ||||||||
Date of first compliant Open Access: | 15 August 2017 | ||||||||
Funder: | Engineering and Physical Sciences Research Council (EPSRC), Royal Society (Great Britain). University Research Fellowship | ||||||||
Grant number: | EP/L020424/1 (EPSRC), UF100592 (RS) |
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