Novel bis(aminoalcohol)oxalamide organogelators and their diglycolylamide analogs: evaluation of gelation efficiency in various organic fluids

Abstract

Three modular types of bis(aminoalcohol)oxalamides (1, 4, and 7) and bis(aminoalcohol)diglycolylamide (8) gelators have been prepared by the reaction of the respective aminoalcohols with oxalyl and digycolyl methylesters as potential low-molecular-weight organogelators. The gelation properties of these amides have been evaluated in various aromatic organic solvents (xylene, toluene, isopropyl benzene, and aromatic ether type organic fluids such as anisole or α -phenylethylmethylether) as well as the long-chain aliphatic alcohols (1-hexanol, 1-octanol, 2-octanol, and aromatic 1-phenylethanol). The compounds with sec-butyl and ethyl side chains produce good gelation properties in both aromatic and other organic fluids. Furthermore, the common oxalamide linker present in the gelators was replaced by an extended diglycolylamide linker (8) and its behaviors were compared with the benzylic oxalamide analog (3). The gelator (8) gives the best results with aromatic fluid and lauric acid ethyl ester.1 H NMR studies reveal the existence of temperaturedependent network assembly/dissolution equilibrium and produce K gel . FTIR was employed to see the effect of hydrogen bonding in the formation of gel network. Thermodynamic parameters regarding gel-to-sol transition were collected with van't Hoff relationships.

The Effect of Branched Alkyl Chain Length on the Properties of Supramolecular Organogels from Mono-N-Alkylated Primary Oxalamides

“…Oxalamide compounds are of considerable interest due to their potential in biomedical applications [34][35][36][37][38][39][40][41][42][43][44][45], catalysis [46][47][48], foods [49], and self-assembling behavior to form gels [50][51][52][53][54][55][56]. The oxalamide functional group consists of two amide groups next to each other in reverse mode, connected by two consecutive carbonyl groups, which has been extensively used as supramolecular synthon to generate LMWGs [50][51][52][53][54][55][56][57][58].…”

“…Oxalamide compounds are of considerable interest due to their potential in biomedical applications [34][35][36][37][38][39][40][41][42][43][44][45], catalysis [46][47][48], foods [49], and self-assembling behavior to form gels [50][51][52][53][54][55][56]. The oxalamide functional group consists of two amide groups next to each other in reverse mode, connected by two consecutive carbonyl groups, which has been extensively used as supramolecular synthon to generate LMWGs [50][51][52][53][54][55][56][57][58]. A variety of bis, homo and hetero-functionalized bolaform, oxalamide-based gelators have been reported over the past two decades [50][51][52][53][54][55][56], while only two reports of mono-functionalized, primary oxalamide gelators exist to date [57,58].…”

“…The oxalamide functional group consists of two amide groups next to each other in reverse mode, connected by two consecutive carbonyl groups, which has been extensively used as supramolecular synthon to generate LMWGs [50][51][52][53][54][55][56][57][58]. A variety of bis, homo and hetero-functionalized bolaform, oxalamide-based gelators have been reported over the past two decades [50][51][52][53][54][55][56], while only two reports of mono-functionalized, primary oxalamide gelators exist to date [57,58]. Thus the present study aims to report new LMWGs based on mono-N-alkylated primary oxalamides (Scheme 1) and evaluate the effect of different sized, branched tail-groups on the supramolecular gelation behavior and gel properties.…”

Hybrid hydrogels derived from renewable resources as a smart stimuli responsive soft material for drug delivery applications

“…Among these building blocks, amino alcohols are of much industrial importance on account of their potential usefulness in the manufacture of pharmaceuticals, surfactants, agrochemicals and lubricating oil additives. 8 In the past 2 decades, gelators derived by molecular self-assembly of amino alcohol such as bis(amino acid)oxalamides, 9 bis(amino alcohol)oxalamides, 9,10 bis(aminoalcohol)diglycolamides, 10 bis(phenylglycinol)malonamide, 11 lipopeptides were extensively studied and their potential application in biology and medicine were explored. 12,13 It is worth mentioning that dopamine an important amino alcohol largely explored in the eld of medicine, coatings, water puri-cation, sensors energy storage, and disease treatment.…”