Chemical Modifications to Structurally-Simple Low Molecular Mass Organogels

Abstract

1,3:2,4 Dibenzylidene-D-sorbitol (DBS) is the gold-standard for low-molecular-weight organogelators (LMOG). Derivatives of DBS and dimethyl urea, the smallest known LMOGs, have been developed to isolate and determine which molecular features are essential for organogelators to form self-assembled fibrillary networks (SAFiNs). For this study, π-π stacking and hydrogen-bonding are the primary non-covalent interactions that are examined. It is expected that π-π stacking is a strong contributing factor towards gelation. The synthesis and testing of 1,3:2,4 dicyclohexanecarboxylidene-D-sorbitol (DCHS), removed π-π stacking potential, but conserved all other aspects of DBS, giving an excellent basis for comparison. DCHS was found to form a gel in 1 of 23 solvents as compared to DBS which managed to form gels in 17 of 23 solvents.