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Self-assembling chiral gelators for fluorinated media

Self-assembling chiral gelators for fluorinated media

Côte, Marie, Nicholls, Tim, Knight, David W., Morgan, Ian R., Rogueda, Philippe G. A., King, Stephen M., Heenan, Richard K. and Griffiths, Peter C. ORCID: 0000-0002-6686-1271 (2009) Self-assembling chiral gelators for fluorinated media. Langmuir, 25 (15). pp. 8678-8684. ISSN 0743-7463 (Print), 1520-5827 (Online) (doi:10.1021/la804277z)

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Abstract

Formulations involving partially and fully fluorinated media represent a technological challenge given the lipophobic and hydrophobic nature of such liquids. The identification of self-associating materials with which to control the viscosity and solubilizing characteristics of fluorinated solvents is a particularly interesting area of research. It is shown here that the presence of the stereogenic centers inherent in a family of bis-(α,β-dihydroxy ester)s is an essential requirement for the thermoreversible gelation of mixtures of partially fluorinated liquids 2H,3H-perfluoropentane (HPFP) and 1H,1H-heptafluorobutanol (HFB). Gelation is driven by hydrogen bonding, which induces a nonpreferred conformation around the bis-(α,β-dihydroxy ester) structural motif. An analysis of the melting temperature yields an enthalpy of melting that is consistent with three to four hydrogen bonds, commensurate with the end-group structure of the gelator. Small-angle neutron scattering demonstrated the existence of the common fibrillar structures whose dimensions showed no obvious correlation with the molecular structure of the gelator.

Item Type: Article
Additional Information: [1] First published online: 29 April 2009.
Uncontrolled Keywords: chiral gelators, fluorinated media
Subjects: Q Science > QD Chemistry
R Medicine > RS Pharmacy and materia medica
Faculty / Department / Research Group: Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 08 Dec 2016 15:16
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/9484

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