ASSEMBLED DIBENZYLIDENE SORBITOL DERIVATIVES: AS A CONFINED REACTION MEDIA AND FUNCTIONAL MATERIALS

Abstract

Low molecular weight gels (LMWG) undergo self-assembly to form 3D networks that are capable of immobilizing the solvent to form a gel. Over a century, Dibenzylidene sorbitol (DBS), a versatile carbohydrate-based LMWG is well known for its gelation abilities in numerous solvents. It is widely applicable in many industries from personal care to pharmaceuticals. The versatility of DBS stems from its unique combination of hydrophilic hydroxy groups and hydrophobic phenyl groups. By modifying these functional units, various DBS derivatives have been synthesized, and have displayed distinct properties and applications. This study aims to synthesize a new class of DBS derivatives and investigate their potential applications across multiple fields, as well as their utility in organic reactions as a confined reaction media. An oligomeric dialdehyde derivative of DBS (HBSD) displayed gelation in NMP solvent. Utilizing high solubility for H2S gas in NMP, a pH-responsive H2S drug delivery system has been developed. In addition, by adopting the co-gelation process, polyphenylene sulfide is generated in a confined reaction media. Eutectogel is derived from 4-(hydroxymethyl)-1,3:2,4-dibenzylidene-D-sorbitol (HMDBS) and utilized as a confined media for photochemical reaction for the regioselective synthesis of 4-arylamino-1,2-naphthoquinones in good yield. Mono- and di-tetrazole DBS derivatives were generated from 4-(cyano)-1,3:2,4 dibenzylidene-D-sorbitol (DNDBS) and sodium azide in confined reaction media by adopting a co-gelation process. Among metallogels prepared from di-tetrazole DBS (DTZDBS), Eu3+ DTZDBS metallogel displayed potential in the fabrication of stimuli-responsive, self-healing Schottky diode. Furthermore, the research highlights the versatility of DBS as a building block for designing advanced materials with tailored properties and it demonstrates the potential of gel derived from DBS derivatives in organic reactions as a confined media.