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Formation of gel and fibrous microstructures by 1-alkyne amphiphiles bearing L-serine headgroup in organic solvents

Ragunathan, Kaliappa G and Bhattacharya, Santanu (1995) Formation of gel and fibrous microstructures by 1-alkyne amphiphiles bearing L-serine headgroup in organic solvents. In: Chemistry and Physics of Lipids, 77 (1). pp. 13-23.

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The study of amphiphiles that form non-spheroidal, and other assemblies, upon solvation is the key to understanding the :relationship between molecular structure and supramolecular morphology. With this aim in mind, we have employed $_L-serine$ and $_L-histidine$ derivatives that are linked via amide bond to hydrophobic chain. $_L-Serine$ amphiphiles form gels in $CHC1_3$, $CH_2C1_2$ and $CC1_4$. Microscopic examinations of these gels reveal the coexistence of tubules, helical ribbons, and spheres. On the other hand, they produce only spherical structures and rods when dispersed in aqueous media (phosphate buffer). In contrast, amphiphiles based on the $_L-histidine$ group, neither formed any gel nor produced any microstructures in non-aqueous solvents like $CHC1_3$, but produced spherical structures and helical rods in water. We also examined the effect of introducing 1-yne or 1-ene moieties into the hydrocarbon chain of such amphiphiles. These moieties, when present in the hydrophobic segment, do not perturb the supramolecular assembly features of the respective serine amphiphiles. Actually, 1-yne moiety, when present in the hydrophobic portion of the amphiphiles, gives characteristic UV-fine structures upon aggregation in water and might be used as a non-invasive marker for probing critical aggregate concentration.

Item Type: Journal Article
Publication: Chemistry and Physics of Lipids
Publisher: Elsevier B.V.
Additional Information: Copyright belongs to Elsevier B.V.
Keywords: Serine amphiphiles;Histidine amphiphiles;1-yne moiety;Chloroform gel;Helical ribbons;Tubules;Multilamellar spherical structures.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 18 Jun 2008
Last Modified: 19 Sep 2010 04:46
URI: http://eprints.iisc.ac.in/id/eprint/14502

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