title: Bile acid alkylamide derivatives as low molecular weight organogelators: systematic gelation studies and qualitative structural analysis of the systems.
abstract: A series of amino- and hydroxyalkyl amides of bile acids have been synthesized and characterized by Fourier transform infrared spectroscopy (FTIR), (1)H and (13)C nuclear magnetic resonance spectroscopy (NMR), as well as electrospray ionization mass spectrometry (ESI-MS) measurements. The ability of the synthesized molecules to promote gel formation was systematically investigated. Out of 396 combinations formed by 11 compounds and 36 different solvents, 22 gel-containing systems were obtained with 1% (w/v) gelator concentration. Apart from one exception, the gelator compounds were lithocholic acid derivatives. This challenges the general trend of bile acid-based physical gelators, according to which the gelation ability of lithocholic acid derivatives is poor. A correlation between the values of Kamlet-Taft parameters and solvent preferences for gelators was observed. The morphologies of the solid and gel structures studied with scanning electron microscopy (SEM) showed variability from fibers to spherical microscale aggregates, the latter of which are unique among bile acid-based organogels. The gels exhibited more complex behavior than was previously established with bile acid derivatives, judging by the microscale diversity present in gelating and non-gelating systems and the tendency for polymorphism. This study underlines the importance of both the molecular and colloidal scale aspects of the gelation phenomenon.
authors.affiliation: Department of Chemistry, P.O. Box 35, FI-40014 University of Jyväskylä, Finland. miika.s.lofman@jyu.fi
authors.forename: Miika
authors.initials: M
authors.lastname: Löfman
authors.forename: Juha
authors.initials: J
authors.lastname: Koivukorpi
authors.forename: Virpi
authors.initials: V
authors.lastname: Noponen
authors.forename: Hannu
authors.initials: H
authors.lastname: Salo
authors.forename: Elina
authors.initials: E
authors.lastname: Sievänen
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D001647:Bile Acids and Salts / Q000138:chemical synthesis / Q000737:chemistry*; D005782:Gels / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D008970:Molecular Weight; D010316:Particle Size; D013237:Stereoisomerism; D013499:Surface Properties
chemical_list: D000577:Amides; D001647:Bile Acids and Salts; D005782:Gels