A Family of Low‐Molecular‐Weight Hydrogelators Based on L‐Lysine Derivatives with a Positively Charged Terminal Group
- 30 December 2002
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (1), 348-354
- https://doi.org/10.1002/chem.200390030
Abstract
A family of L-lysine-based low-molecular-weight compounds with various positively charged terminals (pyridinium and imidazolium derivatives) was synthesized and its gelation behavior in water was investigated. Most of the compounds can be very easily synthesized in high yields (total yields >90 %), and they function as excellent hydrogelators that form hydrogels below 1 wt %; particularly, Nε-lauroyl-Nα-[11-(4-tert-butylpyridinium)undecanoyl]-L-lysine ethyl ester (2 c) and Nε-lauroyl-Nα-[11-(4-phenylpyridinium)undecanoyl]-L-lysine ethyl ester (2 d), which are able to gel water at concentration of only 0.2 wt %. This corresponds to a gelator molecule that entraps more than 20 000 water molecules. All hydrogels are very stable and maintain the gel state for at least 9 months. TEM observations demonstrated that these hydrogelators self-assemble into a nanoscaled fibrous structure; a three-dimensional network is then formed by the entanglement of the nanofibers. An FTIR study in [D6]DMSO/D2O and in CHCl3 revealed the existence of intermolecular hydrogen bonding between the amide groups. This was further supported by a 1H NMR study in [D6]DMSO/H2O. A luminescence study, in which ANS (1-anilino-8-naphtharenesulfonic acid) was used as a probe, indicated that the hydrogelators self-assemble into nanostructures possessing hydrophobic pockets at a very low concentration. Consequently, it was found that the driving forces for self-assembly into a nanofiber are hydrogel bonding and hydrophobic interactions.This publication has 48 references indexed in Scilit:
- New low-molecular-weight hydrogelators based on L-lysine with positively charged pendant chainNew Journal of Chemistry, 2002
- Gold Nanoparticle/Hydrogel Composites with Solvent-Switchable Electronic PropertiesAdvanced Materials, 2001
- Supramolecular dendritic two-component gelChemical Communications, 2001
- Lyotropic Aggregate of Tripeptide Derivatives within Organic Solvents: Relationship between Interpeptide Hydrogen Bonding and Packing Arrangements of ComponentsLangmuir, 2001
- Self-Assembly of a Liquid Crystalline Anisotropic GelChemistry of Materials, 2000
- Hexatriacontane Organogels. The First Determination of the Conformation and Molecular Packing of a Low-Molecular-Mass Organogelator in Its Gelled StateLangmuir, 2000
- Physical Gelation of Nematic Liquid Crystals with Amino Acid Derivatives Leading to the Formation of Soft Solids Responsive to Electric Field.Journal of Photopolymer Science and Technology, 2000
- Vesicle and Tubular Microstructure Formation from Synthetic Sugar-Linked Amphiphiles. Evidence of Vesicle Formation from Single-Chain Amphiphiles Bearing a Disaccharide HeadgroupLangmuir, 1999
- Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexesChemical Communications, 1997
- Dynamic interactions of fluorescence probes with the solvent environmentJournal of the American Chemical Society, 1976