A1 Journal article (refereed)
Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides (2018)


Kuosmanen, R., Puttreddy, R., Rissanen, K., & Sievänen, E. (2018). Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides. Chemistry: A European Journal, 24(70), 18676-18681. https://doi.org/10.1002/chem.201803151


JYU authors or editors


Publication details

All authors or editors: Kuosmanen, Riikka; Puttreddy, Rakesh; Rissanen, Kari; Sievänen, Elina

Journal or series: Chemistry: A European Journal

ISSN: 0947-6539

eISSN: 1521-3765

Publication year: 2018

Volume: 24

Issue number: 70

Pages range: 18676-18681

Publisher: Wiley-VCH

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/chem.201803151

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/60802


Abstract

The self-assembly properties of nine low-molecular-weight gelators (LMWGs) based on bile acid alkyl amides were studied in detail. Based on the results, the number of hydroxyl groups attached to the steroidal backbone plays a major role in the gelation, although the nature of the aliphatic side chain also modulates the gelation abilities. Of the 50 gel systems studied, 35 are based on lithocholic acid and 15 on cholic acid derivatives. The deoxycholic acid derivatives did not form any gels. The gelation occurred primarily in aromatic solvents and the gels manifested typical fibrous or spherical morphologies. The 13C cross-polarized magic angle spinning (CPMAS) NMR spectra measured on the crystalline materials and the corresponding wet organogels were analogous, suggesting that the chemical environments, that is, the intermolecular interactions found in the two materials were similar. The single-crystal X-ray structures of all nine bile-acid amide derivatives studied revealed very similar molecular conformations in the solid state and gave insights into the possible intermolecular interactions in the gel state.


Keywords: supramolecular chemistry; gels; amides; x-ray crystallography; NMR spectroscopy

Free keywords: bile acid amides; supramolecular gels; intermolecular interactions


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Ministry reporting: Yes

Reporting Year: 2018

JUFO rating: 2


Last updated on 2023-10-01 at 12:37