Supramolecular Gels Derived from the Salts of Variously Substituted Phenylacetic Acid and Dicyclohexylamine: Design, Synthesis, Structures, and Dye Adsorption

Abstract

A well-studied supramolecular synthon, namely, secondary ammonium monocarboxylate (SAM), was exploited to generate a new series of organic salts derived from variously substituted phenylacetic acid and dicyclohexylamine as potential low-molecular-weight gelators. As much as 25 % of the SAM salts under study were gelators. The gels were characterized by rheology, and the morphology of the gel networks was studied by high-resolution electron microscopy. Single-crystal and powder XRD data were employed to study structure-property (gelation) correlations. One of the gels could adsorb a hydrophobic dye (Nile Red) more efficiently than that of a hydrophilic dye (Calcein) from dimethyl sulfoxide; this might provide useful clues towards the development of stain-removing gels.

Supramolecular Gels Based on C3-Symmetric Amides: Application in Anion-Sensing and Removal of Dyes from Water

“…Supramolecular gels based on low-molecular-weight gelators (LMWGs) [9][10][11][12][13] are excellent candidates for use in adsorption studies due to their porous networks and stimuli-responsive properties [14][15][16][17][18][19]. LMWGs display superior adsorption capacities for dyes [20][21][22][23], but the majority of LMWGs reported for the removal of dyes are metallogels or pH-dependent [14,[24][25][26][27][28].…”

Catalytic Gels for a Prebiotically Relevant Asymmetric Aldol Reaction in Water: From Organocatalyst Design to Hydrogel Discovery and Back Again

“…In some cases, gelation requires two distinct chemical componentssuch “two-component gels” are tunable but relatively rare, especially in the case of hydrogels that self-assemble from LMWGs in water. Examples include systems in which the two components form a non-covalent complex that acts as the LMWG, or in which they come together to form the LMWG in a dynamic reaction, such as acylhydrazone formation . There are also examples of small molecules that undergo dynamic reactions, like imine formation, to form polymer network hydrogels, but such gels are more like polymer gels than those that self-assemble from LMWGs via non-covalent interactions.…”

Acid–ammonium heterodimer and N(ammonium)–H...N(pyridine) synthon preference in three salts of nicotinic acid with (1R,2R)-1,2-diphenylethylenediamine

“…Generally, the assessment of robust synthons is based on the frequency of synthon formation among all structures containing the necessary functional group components, and a higher occurrence probability suggests a greater utility in the design of salts and cocrystals (Srirambhatla et al, 2014;Kumar et al, 2018). In addition, the charge-assisted hydrogen bonds have also played important roles in designing molecular solids, such as the supramolecular gels made from phenylacetic acid with dicyclohexylamine and pharmaceutical cocrystals derived from pyrazinecarboxamide and various carboxylic acids (Adalder et al, 2012;Roy et al, 2018).…”