4.6 Article

Stigmasterol-Based Novel Low Molecular Weight/Mass Organic Gelators

Journal

MOLECULES
Volume 16, Issue 11, Pages 9357-9367

Publisher

MDPI
DOI: 10.3390/molecules16119357

Keywords

stigmasterol; L-phenylalanine; ester; amide; supramolecule; low molecular weight/mass organic gelators

Funding

  1. Czech Science Foundation [P503/11/0616]
  2. Ministry of Education, Youth and Sports of the Czech Republic [OC09039 (COST Action CM0701), OC10001 (COST Action CM0804)]
  3. Institute of Chemical Technology in Prague (Ministry of Education, Youth and Sports of the Czech Republic) [MSM6046137305]

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Conjugates consisting of stigmasterol and L-phenylalanine, interconnected through short-chained dicarboxylic acyls by ester and amide bonds, respectively, were synthesized as potential low molecular weight/mass organic gelators (LMWGs/LMMGs). Their physico-chemical properties were subjected to investigation, especially their ability to form gels reversibly based on changes of the environmental conditions. Other self-assembly properties detectable by UV-VIS traces were measured in systems consisting of two miscible solvents (water/acetonitrile) with varying solvent ratios and using constant concentrations of the studied compounds. Partition and diffusion coefficients and solubility in water were calculated for the target conjugates. The conjugate 3a was the only compound from this series capable of forming a gel in 1-octanol. All three conjugates 3a-3c displayed supramolecular characteristics in the UV-VIS spectra.

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