This study explains the principal aspects of why the classic gelator 1:3,2:4-dibenzylidene sorbitol (DBS) and five of its analogs do or do not form gels in 23 different organic solvents. The most important factors influencing the gelation ability include, but are not limited to, H-bonding by its primary and secondary hydroxyl groups. Chemical modification of DBS in this study shows how hydrogen bonding at different positions could alter the Hansen Solubility Parameters (HSP) attributed to gelation. While each hydroxyl group assists gelation, removal of either affects gelation ability. It alters the location of dichroic absorbance differences parallel and perpendicular to the axes of fibers constituting the SAFiNs. Solvent type had a significant effect on the microstructure of the gels and provided intriguing insights. For 5-deoxy-DBS, for example, in toluene, removing the secondary hydroxyl led to highly branched nanofibers; elimination of the primary hydroxyl group produced long and thin fibers. Plotting the gelation results of HSPs and modifications of the individual molecular synthons provides valuable insights to understand self-assembly mechanisms.

Assessing the role of Molecular Synthons that alters 1,3:2,4 Dibenzylidene Sorbitol Self-Assembled Fibrillar Networks’ Molecular Alignment

ACS Fall 2021

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