Surface and Self‐Aggregation Properties of Bis‐Benzimidazolones Derivatives of d‐Glucose

Abstract

The surface and self-aggregation properties in water of a new series of amphiphilic homologues, bisbenzimidazolone derivatives of D-glucose, were investigated. Parameters such as the maximal surface excess concentration, minimal area per molecule at the interface, and critical micelle concentration (CMC) were found to be significantly dependent on the hydrophobic alkyl chain length. The synthesized compounds form micelles at remarkably low concentrations, and CMCs derived from surface tension measurements show a minimum as a function of the alkyl chain length; this unusual trend can be attributed to the formation of submicellar aggregates in compounds with long alkyl chains, as evidenced from fluorescence probe spectroscopy data. At high surfactant concentrations, lyotropic liquid crystalline phases with hexagonal structure are formed. Small angle X-ray scattering measurements indicate that the characteristic nanoscopic lengths increase with water swelling and alkyl chain length.

Surfactants Based on Bis‐Galactobenzimidazolones: Synthesis, Self‐Assembly and Ion Sensing Properties

“…In a continuation of our previous work in this area [26][27][28][29], we have synthesized a series of new non-ionic amphiphiles based on bis-galactobenzimidazolone (see Fig. 1a), which was prepared by grafting the 6-O-[2,3-epoxypropyl]-1,2:3,4-di-O-isopropylidene-a-galactopyranose group on the N-3 nitrogen atom of two benzimidazolone units that are linked by an alkyloxypropylene group in the same conditions as described earlier [29], following by the deprotection of diacetonide galactopyranose moiety [28][29][30][31].…”

“…All solvents were distilled before use. The compound N,N 0 -1,3-Bis-[N-3-(6-deoxy-3-O-methyl-D-glucopyranose-6-yl)-2-oxo-benzimidazole-1-yl)]-2-dodecyloxy propane, abbreviated as LBC12, was synthesized as reported in a previous paper [29]. 1,3-N,N 0 -bis-[2-oxobenzimidazol-1-yl]-2-alkyloxypropanes 1a-c were synthesized in three steps.…”

“…The first one is the condensation of N-isopropenylbenzimidazolone [20] with epichlorohydrin in a toluene-DMSO mixture in the presence of potassium carbonate. The second step is the alkylation of the free OH group by n-bromoalkanes in a toluene-DMSO mixture and potassium hydroxide [29]. Subsequent N-3 deprotection in a cold acid medium [20] afforded the corresponding compounds 1a-c.…”

“…1a), which was prepared by grafting the 6-O-[2,3-epoxypropyl]-1,2:3,4-di-O-isopropylidene-a-galactopyranose group on the N-3 nitrogen atom of two benzimidazolone units that are linked by an alkyloxypropylene group in the same conditions as described earlier [29], following by the deprotection of diacetonide galactopyranose moiety [28][29][30][31]. The new synthesis route is easier and involves fewer steps than the previously reported one [29].…”

Tin electrodeposition from sulfate solution containing a benzimidazolone derivative

“…In this study, we were interested in the effect of a new additive; N,N'-1,3-bis-[N-3-(6-deoxy-3-Omethyl-D-glucopyranos-6-yl)-2-oxobenzimidazol-1-yl)]-2-tetradecyloxypropane 11 ( Fig. 1) on the electro-deposition of tin from an acidic solution of tin sulfate.…”