Towards the synthesis of new benzimidazolone derivatives with surfactant properties

Massoui³

et al. 2010

J Surfact & Detergents

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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.

Section: Synthesismentioning

confidence: 99%

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

Massoui³

et al. 2010

J Surfact & Detergents

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“…N,N 0 -1,3-Bis-[N-3-(6-(2 0 -hydroxypropyloxy)-1,2:3,4-di-O-isopropylidene-a-D-galactopyranos-6-yl)-2-oxobenzimid azol-1-yl)]-2-alkyloxypropanes 3a-c were synthesized following Scheme 1, by condensing the 1,3-N,N 0 -bis-[2-oxobenzimidazol-1-yl]-2-alkyloxypropanes 1a-c [29] units with activate galactopyranose 2 in the presence of potassium carbonate and in pure DMSO as solvent [28,29].…”

Section: Synthesismentioning

confidence: 99%

“…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].…”

Section: Introductionmentioning

confidence: 99%

“…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].…”

Section: Introductionmentioning

confidence: 99%

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

Hassan

et al. 2011

J Surfact & Detergents

A series of new non-ionic amphiphiles based on bis-galactobenzimidazolones have been synthesized by grafting alkyl bis-benzimidazolone units as hydrophobic tails on hydroxypropyloxygalacto-pyranose moieties as hydrophilic heads. Their surface and self-aggregation properties in water were evaluated. The compounds show very low critical micellar concentrations (CMCs) that decrease with increasing chain length; values for the minimal area per molecule at the interface (A min ) follow the same trend. The synthesized compounds also form hexagonal liquid crystals in water for a certain range of hydrophobic tail lengths. On the other hand, the new amphiphiles show characteristic UV-Vis absorption and fluorescence emission bands associated with the benzimidazolone moiety. The fluorescence emission is quenched with a certain degree of selectivity by cations, due to their strong affinity towards the benzimidazolone group, which shows ion complexation properties. Hence, the reported new amphiphiles are candidates as self-assembling chemosensors. The quenching efficiency and also ion sensing sensitivity is higher in the monomeric state as compared to the micellar state. The fluorescence emission intensity is higher for compounds with a shorter alkyl chain.

“…Also, some derivatives have been reported to show complexant properties (Cignitti et al, 1995;Htay and Meth-Cohen, 1976a,b;Meth-Cohen et al, 1982). In our previous work, we have shown that some series of glycobenzimidazolone is present an important amphiphilic property (Lakhrissi et al, 2008(Lakhrissi et al, , 2010(Lakhrissi et al, , 2011.…”

Section: Introductionmentioning

confidence: 97%

Mild steel corrosion inhibition in 200 ppm NaCl by new surfactant derivatives of bis-glucobenzimidazolones

Arabian Journal of Chemistry

Touir

et al. 2017

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The new bis-glucobenzimidazolone derivatives (24a-d) have been synthesized and characterized by NMR spectroscopy. They have been tested as corrosion inhibitor for mild steel in 200 ppm NaCl solution using potentiodynamic polarization curves and electrochemical impedance spectroscopy. Potentiodynamic polarization curve measurements showed that the investigated compounds were a mixed-type inhibitor. Their inhibition efficiencies improve with concentration and reached a maximum at 10 À5 M of each compound and the 24b is better. Electrochemical impedance spectroscopy measurements showed that the diagrams composed of two depressed capacitive loops. This loop can be split into two capacities' contributions, although badly separated. The first loop is attributed to the formation of a protective layer and the second is attributed to the charge transfer resistance.