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Co-existence of distinct supramolecular assemblies in solution and in the solid state
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Reddy, Manjunatha, Huqi, Aida, Iuga, Dinu, Sakurai, Satoshi, Marsh, Andrew, Davis, Jeffery T., Masiero, Stefano and Brown, Steven P. (2016) Co-existence of distinct supramolecular assemblies in solution and in the solid state. Chemistry - A European Journal, 23 (10). pp. 2315-2322. doi:10.1002/chem.201604832 ISSN 0947-6539.
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Official URL: http://dx.doi.org/10.1002/chem.201604832
Abstract
The formation of distinct supramolecular assemblies, including a metastable species, is revealed for a lipophilic guanosine (G) derivative in solution and in the solid state. Structurally different G-quartet based assemblies are formed in chloroform depending on the nature of the cation, anion and salt concentration, as characterized by circular dichroism and time course diffusion-ordered NMR spectroscopy data. Intriguingly, even the presence of potassium ions that stabilize G-quartets in chloroform was insufficient to exclusively retain such assemblies in the solid state, leading to the formation of mixed quartet and ribbon-like assemblies as revealed by fast magic-angle spinning (MAS) NMR spectroscopy. Distinct N-H∙∙∙N and N-H∙∙∙O intermolecular hydrogen bonding interactions drive quartet and ribbon-like self-assembly resulting in markedly different 2D 1H solid-state NMR spectra, thus facilitating a direct identification of mixed assemblies. A dissolution NMR experiment confirmed that the quartet and ribbon interconversion is reversible - further demonstrating the changes that occur in the self-assembly process of a lipophilic nucleoside upon a solid-state to solution-state transition and vice versa. A systematic study for complexation with different cations (K+, Sr2+) and anions (picrate, ethanoate and iodide) emphasises that the existence of a stable solution or solid-state structure may not reflect the stability of the same supramolecular entity in another phase.
Item Type: | Journal Article | ||||||||||||||||||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||||||||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Science > Physics |
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Library of Congress Subject Headings (LCSH): | Supramolecular chemistry, Solution (Chemistry), Solid state chemistry | ||||||||||||||||||||||||
Journal or Publication Title: | Chemistry - A European Journal | ||||||||||||||||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||||||||||||||||||
ISSN: | 0947-6539 | ||||||||||||||||||||||||
Official Date: | 29 November 2016 | ||||||||||||||||||||||||
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Volume: | 23 | ||||||||||||||||||||||||
Number: | 10 | ||||||||||||||||||||||||
Page Range: | pp. 2315-2322 | ||||||||||||||||||||||||
DOI: | 10.1002/chem.201604832 | ||||||||||||||||||||||||
Status: | Peer Reviewed | ||||||||||||||||||||||||
Publication Status: | Published | ||||||||||||||||||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||||||||||||||||||
Date of first compliant deposit: | 6 December 2016 | ||||||||||||||||||||||||
Date of first compliant Open Access: | 29 November 2017 | ||||||||||||||||||||||||
RIOXX Funder/Project Grant: |
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