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Issue 23, 2009
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Soft ordered mesoporous materials from nonionic isoprenoid-type monoethanolamide amphiphiles self-assembled in water

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Abstract

The thermal and lyotropic liquid crystalline phase behaviour of a series of amide and monoethanolamide amphiphiles with isoprenoid-type hydrocarbon chains has been investigated. The amphiphilic nature of these molecules combined with their ability to form nanostructured self-assemblies makes them ideal candidates as delivery vehicles of bioactive molecules. For both families of molecules, increased branching in the hydrophobic chain, associated with increasing chain length, results in a decreased melting point. The melting points of the amides are significantly higher than their monoethanolamide homologues. Interestingly, both hexahydrofarnesoyl (H-farnesoyl) and phytanoyl monoethanolamide exhibit a glass transition temperature at around −72 °C to −74 °C. H-Farnesoyl and phytanoyl monoethanolamide form lyotropic liquid crystalline phases in water, whilst H-farnesoyl and phytanoyl amide form a spontaneous emulsion at the amphiphile–water interface. In particular, at room temperature H-farnesoyl and phytanoyl monoethanolamide form the Schwarz diamond (QIID) and the Schoen gyroid (QIIG) bicontinuous cubic phases which are retained down to temperatures as low as 1 °C. Furthermore, phytanoyl monoethanolamide displays a QIID, QIIG and inverse hexagonal phase (HII) at physiological temperature. Both phytanoyl and H-farnesoyl monoethanolamide form mesoporous cubic phases at room temperature that are easily dispersed into cubosomes. The robust nature of the nanostructured phase formation of these two monoethanolamides over a wide range of temperatures makes them ideal candidates for a variety of applications.

Graphical abstract: Soft ordered mesoporous materials from nonionic isoprenoid-type monoethanolamide amphiphiles self-assembled in water

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Supplementary files

Article information


Submitted
16 Apr 2009
Accepted
10 Aug 2009
First published
02 Oct 2009

Soft Matter, 2009,5, 4823-4834
Article type
Paper

Soft ordered mesoporous materials from nonionic isoprenoid-type monoethanolamide amphiphiles self-assembled in water

S. M. Sagnella, C. E. Conn, I. Krodkiewska and C. J. Drummond, Soft Matter, 2009, 5, 4823
DOI: 10.1039/B907596H

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