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Quadruply hydrogen bonded cytosine modules for supramolecular applications

Quadruply hydrogen bonded cytosine modules for supramolecular applications
Quadruply hydrogen bonded cytosine modules for supramolecular applications
In view of the range of properties required from supramolecular materials, there is clearly a need for new strong quadruple hydrogen bonded modules, which can be used in polymer or copolymer synthesis via the self- or hetero-association of complimentary units. A cytosine-based module has been prepared for supramolecular applications using a straightforward synthetic approach. The cytosine module was designed such that it does not undergo tautomeric changes observed with ureidopyrimidinones. The cytosine module was capable of forming quadruple hydrogen bonded assemblies both in solution and in the solid state, and the structure of the dimeric self-assembled unit was confirmed by single-crystal X-ray and solution NMR techniques. The dimerization constant was estimated to be greater than 9 × 106 M-1 in deuterated benzene. The capacity of the cytosine-based module to strongly hetero-associate with the ureidopyrimidinone module was demonstrated, and a supramolecular polymer of a bifunctional unit incorporating the cytosine module and PEG-based linker was described.
bonding motifs, dimers, heterodimer, association, systems
0002-7863
6544-6545
Lafitte, Valérie G.H.
b818e619-5ac6-4696-824e-75f88486bcf3
Aliev, Abil E.
b52589ec-2e49-447b-a1e3-2ec2eca9932c
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bala, Kason
9cf0c84c-b02d-4345-a996-aebc7752791a
Golding, Peter
8d1cfb00-6d1a-4bc4-991c-9a8e5fa9a532
Hailes, Helen C.
e4e3410f-b56a-4efc-88da-24091f348dc3
Lafitte, Valérie G.H.
b818e619-5ac6-4696-824e-75f88486bcf3
Aliev, Abil E.
b52589ec-2e49-447b-a1e3-2ec2eca9932c
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Bala, Kason
9cf0c84c-b02d-4345-a996-aebc7752791a
Golding, Peter
8d1cfb00-6d1a-4bc4-991c-9a8e5fa9a532
Hailes, Helen C.
e4e3410f-b56a-4efc-88da-24091f348dc3

Lafitte, Valérie G.H., Aliev, Abil E., Horton, Peter N., Hursthouse, Michael B., Bala, Kason, Golding, Peter and Hailes, Helen C. (2006) Quadruply hydrogen bonded cytosine modules for supramolecular applications. Journal of the American Chemical Society, 128 (20), 6544-6545. (doi:10.1021/ja0587289).

Record type: Article

Abstract

In view of the range of properties required from supramolecular materials, there is clearly a need for new strong quadruple hydrogen bonded modules, which can be used in polymer or copolymer synthesis via the self- or hetero-association of complimentary units. A cytosine-based module has been prepared for supramolecular applications using a straightforward synthetic approach. The cytosine module was designed such that it does not undergo tautomeric changes observed with ureidopyrimidinones. The cytosine module was capable of forming quadruple hydrogen bonded assemblies both in solution and in the solid state, and the structure of the dimeric self-assembled unit was confirmed by single-crystal X-ray and solution NMR techniques. The dimerization constant was estimated to be greater than 9 × 106 M-1 in deuterated benzene. The capacity of the cytosine-based module to strongly hetero-associate with the ureidopyrimidinone module was demonstrated, and a supramolecular polymer of a bifunctional unit incorporating the cytosine module and PEG-based linker was described.

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More information

Published date: 2006
Keywords: bonding motifs, dimers, heterodimer, association, systems

Identifiers

Local EPrints ID: 44475
URI: http://eprints.soton.ac.uk/id/eprint/44475
ISSN: 0002-7863
PURE UUID: e5ad7f95-61ae-454a-8a2d-9c4b8f00d684
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 07 Mar 2007
Last modified: 03 Dec 2019 01:54

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