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Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents

Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents
Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents
A series of pyridyl guanidinium–carboxylates has been prepared and the dimeric self-assembly of these studied in H2O/DMSO mixtures, principally using dilution isothermal calorimetry. Compounds 5 and 6, incorporating an aromatic ring in the “tethering” region between the guanidinium and carboxylate groups, demonstrate the strongest dimerisation in neat DMSO. X-ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid-state, but both involve carboxylate–guanidinium salt bridges as anticipated, and ?–? interactions. Compounds 10–16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino acid content, but also sustained dimerisation under increasingly aqueous conditions, up to 50?% H2O/DMSO in the case of 14 and 15. The extent of our study in H2O/DMSO mixtures was determined by substrate solubility of 10–16, and not the limit of self-assembly.
calorimetry, dimerization, molecular recognition, self-assembly, supramolecular chemistry
0947-6539
12387-12397
Ashiq, Muhammad. Irfan
769163ac-7826-4c48-af0a-a1191b885553
Tesfatsion, Biniam. F.
38515ebf-8cc6-4abb-abbd-15d191f57ef5
Gaggini, Francesca
e17b842d-e822-4692-8c42-c612ee639510
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Ashiq, Muhammad. Irfan
769163ac-7826-4c48-af0a-a1191b885553
Tesfatsion, Biniam. F.
38515ebf-8cc6-4abb-abbd-15d191f57ef5
Gaggini, Francesca
e17b842d-e822-4692-8c42-c612ee639510
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Ashiq, Muhammad. Irfan, Tesfatsion, Biniam. F., Gaggini, Francesca, Dixon, Sally and Kilburn, Jeremy D. (2010) Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents. Chemistry - A European Journal, 16 (41), 12387-12397. (doi:10.1002/chem.201001861). (PMID:20857461)

Record type: Article

Abstract

A series of pyridyl guanidinium–carboxylates has been prepared and the dimeric self-assembly of these studied in H2O/DMSO mixtures, principally using dilution isothermal calorimetry. Compounds 5 and 6, incorporating an aromatic ring in the “tethering” region between the guanidinium and carboxylate groups, demonstrate the strongest dimerisation in neat DMSO. X-ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid-state, but both involve carboxylate–guanidinium salt bridges as anticipated, and ?–? interactions. Compounds 10–16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino acid content, but also sustained dimerisation under increasingly aqueous conditions, up to 50?% H2O/DMSO in the case of 14 and 15. The extent of our study in H2O/DMSO mixtures was determined by substrate solubility of 10–16, and not the limit of self-assembly.

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More information

Published date: 2 November 2010
Keywords: calorimetry, dimerization, molecular recognition, self-assembly, supramolecular chemistry

Identifiers

Local EPrints ID: 176339
URI: https://eprints.soton.ac.uk/id/eprint/176339
ISSN: 0947-6539
PURE UUID: c24f9ac7-a383-42b8-ad07-0ad650074da0
ORCID for Sally Dixon: ORCID iD orcid.org/0000-0003-2219-3635

Catalogue record

Date deposited: 07 Mar 2011 11:27
Last modified: 06 Jun 2018 12:49

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