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The delicate balance between gelation and crystallisation: structural and computational investigations

The delicate balance between gelation and crystallisation: structural and computational investigations
The delicate balance between gelation and crystallisation: structural and computational investigations
Predicting the ability of low molecular weight molecules to form hydrogels is difficult. Here, we have examined the self-assembly behavior of two chemically and structurally similar functionalized dipeptides, one of which is found to form a meta-stable hydrogel (1) and the other forming a crystalline solid (2). To investigate the reasons for these differences, we have employed computational methods to explore the crystal energy landscapes of the two molecules and examined differences in their preferred packing arrangements. We show that this method accurately predicts the packing for the crystalline solid, 2. Furthermore, the predictions for the gel-former 1 suggest that one-dimensional hydrogen-bonding arranged into tightly coiled molecular columns is a preferred mode of packing for this system, but is unfavorable for 2. The different tendencies of forming these columns could provide an explanation for the different behavior of the two molecules and demonstrate that this approach could be useful for the future predictable design of low molecular weight gelators.



1744-683X
4144-4156
Adams, Dave J.
d95e4f11-7580-43cb-802d-ad8ac0161c8a
Morris, Kyle
da337ec3-3be0-4d48-b42a-5aebcf65dd3d
Chen, Lin
9f2b5d5d-a212-45a4-b315-f8e1db189e5b
Serpell, Louise C.
3a51f573-781c-4c80-bb36-bfc6c8f73c10
Bacsa, John
8877bf1f-d692-4526-b61e-ee3f3c053204
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Adams, Dave J.
d95e4f11-7580-43cb-802d-ad8ac0161c8a
Morris, Kyle
da337ec3-3be0-4d48-b42a-5aebcf65dd3d
Chen, Lin
9f2b5d5d-a212-45a4-b315-f8e1db189e5b
Serpell, Louise C.
3a51f573-781c-4c80-bb36-bfc6c8f73c10
Bacsa, John
8877bf1f-d692-4526-b61e-ee3f3c053204
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636

Adams, Dave J., Morris, Kyle, Chen, Lin, Serpell, Louise C., Bacsa, John and Day, Graeme M. (2010) The delicate balance between gelation and crystallisation: structural and computational investigations. Soft Matter, 6 (17), 4144-4156. (doi:10.1039/C0SM00409J).

Record type: Article

Abstract

Predicting the ability of low molecular weight molecules to form hydrogels is difficult. Here, we have examined the self-assembly behavior of two chemically and structurally similar functionalized dipeptides, one of which is found to form a meta-stable hydrogel (1) and the other forming a crystalline solid (2). To investigate the reasons for these differences, we have employed computational methods to explore the crystal energy landscapes of the two molecules and examined differences in their preferred packing arrangements. We show that this method accurately predicts the packing for the crystalline solid, 2. Furthermore, the predictions for the gel-former 1 suggest that one-dimensional hydrogen-bonding arranged into tightly coiled molecular columns is a preferred mode of packing for this system, but is unfavorable for 2. The different tendencies of forming these columns could provide an explanation for the different behavior of the two molecules and demonstrate that this approach could be useful for the future predictable design of low molecular weight gelators.



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More information

Published date: 7 July 2010
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Computational Systems Chemistry

Identifiers

Local EPrints ID: 343428
URI: https://eprints.soton.ac.uk/id/eprint/343428
ISSN: 1744-683X
PURE UUID: cc32005d-a0b2-4d47-a26e-586eff323efa
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

Catalogue record

Date deposited: 08 Oct 2012 10:50
Last modified: 20 Jul 2019 00:41

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Contributors

Author: Dave J. Adams
Author: Kyle Morris
Author: Lin Chen
Author: Louise C. Serpell
Author: John Bacsa
Author: Graeme M. Day ORCID iD

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