Design, synthesis and stimuli responsive gelation of novel stigmasterol-amino acid conjugates

Research output: Contribution to journalArticleScientificpeer-review

Researchers

Research units

  • University of Jyväskylä
  • Institute of Experimental Botany
  • University of Chemistry and Technology, Prague

Abstract

An efficient synthesis of three novel stigmasterol-amino acid (glycine, L-leucine and L-phenylalanine) conjugates as stimuli responsive gelators is reported. The gelation properties of the prepared compounds were investigated in a variety of organic as well as aqueous solvents. The most striking finding of our investigation was that the hydrochloride salts of the prepared conjugates acted as gelators, whereas the neutral conjugates were either non-gelators or formed only a weak gel in anisole. The hydrochloride salts of stigmasteryl glycinate and L-Ieucinate form gels in n-alcohols (n = 4-10) and in ethane-1,2-diol, and that of stigmasteryl L-phenylalaninate forms gels in aromatic solvents and in tetrachloromethane. These unique properties of the gelators were explored to prepare stimuli responsive, "acid-base" triggered reversible sol-gel transitions. The gelators and their gels were characterized by liquid and solid-state NMR as well as FT-IR. The morphology of their corresponding xerogels was investigated by SEM. (C) 2011 Elsevier Inc. All rights reserved.

Details

Original languageEnglish
Pages (from-to)587-593
Number of pages7
JournalJournal of Colloid and Interface Science
Volume361
Issue number2
Publication statusPublished - 15 Sep 2011
MoE publication typeA1 Journal article-refereed

    Research areas

  • Stigmasterol, Amino acid, LMOG, Organogel, pH responsive, MOLECULAR-MASS GELATORS, SUPRAMOLECULAR GELS, ORGANIC LIQUIDS, ORGANOGELS, SPECTROSCOPY, CHOLESTEROL, TRANSITION, SCATTERING, HYDROGELS

ID: 8688533