Effect of the alkyl chain length on micelle formation for bis(N-alkyl-N,N-dimethylethylammonium)ether dibromides

Brycki, Bogumił; Szulc, Adrianna; Koenig, Hanna; Kowalczyk, Iwona; Pospieszny, Tomasz; Górka, Sara

doi:10.1016/j.crci.2019.04.002

Cited by 20 publications

(14 citation statements)

References 58 publications

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“…For example, an increase in the length of the hydrocarbon chain from 8 to 18 carbon atoms causes a decrease in CMC of 3.46 to 0.06 mM (compounds ( 1 – 6 )). This is in agreement with data presented previously with regard to the relationship between gemini surfactants with the polymethylene linker and spacer functionalized with an ether group [ 42 ]. Comparing the effect of the counterion, it can be stated that bromides have lower CMC than analogous iodides.…”

Section: Resultssupporting

confidence: 93%

“…Based on the data presented, it can be noted that the introduction of additional long hydrocarbon chains to the molecule, causes increases in surface activity and decreases in CMC values. The relationship between log CMC and the number of carbon atoms in a middle hydrophilic chain decreased linearly ( Figure 6 ), analogous to conventional gemini surfactants [ 42 ].…”

Section: Resultsmentioning

confidence: 72%

“…For compounds in the same homologous series, β increases with the elongation of the alkyl chain, reaching the highest value for dodecyl derivative, and then decreases with the elongation of the alkyl chain. This correlation is characteristic of gemini surfactants [ 42 ]. The big value of β is caused by the stronger binding of the counterion to the micelles, suggesting closer packing of the hydrophilic parts of surfactant and higher surface charge density at the micelle solution interface [ 42 ].…”

Section: Resultsmentioning

confidence: 95%

“…This correlation is characteristic of gemini surfactants [ 42 ]. The big value of β is caused by the stronger binding of the counterion to the micelles, suggesting closer packing of the hydrophilic parts of surfactant and higher surface charge density at the micelle solution interface [ 42 ]. The standard Gibbs energy values of the micellization process (ΔG°mic) for gemini surfactants were negative.…”

Section: Resultsmentioning

confidence: 95%

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Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer

et al. 2020

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A series of 21 azapolymethylene gemini surfactants were obtained. The synthesis of the title surfactants in one- or two-step reaction proceeds with good yields. The structure and the purity of the synthesized compounds were determined by 1H and 13C NMR, ESI-MS spectra, and elemental analysis. Moreover, 2D COSY, HMBC, and HSQC spectra were performed. The minimal inhibitory concentrations (MIC) of the synthesized compounds were determined against fungi: Candida albicans, Aspergillus niger, Penicillium chrysogenum and bacteria: Escherichia coli,Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis. Also, the critical micelle concentrations (CMC) were determined. The relationship between antimicrobial and surface activity and surfactant structure has been determined.

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Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 72%

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 95%

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Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer

et al. 2020

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“…Aggregation behaviour of gemini molecules can be controlled by the structural modification of the spacer part of a gemini molecule through the insertion of various functional chemical groups, e.g. sulphur, oxygen, N -methylated nitrogen, methylene [29,30], hydroxy group [31,32]. To a certain extent, the aggregation of cationic gemini molecules is also affected by the modification of alkyl parts, such as cyclododecyl chains [33] or of the molecule head group [34].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis, Self-Assembled Structures, and Microbicidal Activity of Cationic Gemini Surfactants with Branched Tridecyl Chains

et al. 2019

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Cationic gemini surfactants with polymethylene spacer and linear alkyl chains containing an even number of carbon atoms have been extensively studied in the recent past, with the emphasis put on the determination of their aggregation behaviour in aqueous solution and their biological properties. However, the information on the aggregation of branched gemini surfactants with an odd number of carbon atoms in their alkyl chains is only sparsely reported in the literature. To help cover this gap in the research of cationic gemini surfactants, a series of branched bisammonium cationic gemini surfactants with an odd number of carbon atoms in alkyl chains (tridecane-2-yl chains) and a polymethylene spacer with a variable length ranging from 3 to 12 carbon atoms have been synthesized and investigated. Critical micelle concentration, which was determined by three methods, was found to be in the order 10−4 mol/L. A comparison of the obtained data of the novel series of tridecyl chain geminis with those of gemini surfactants with dodecyl chains and an identical spacer structure revealed that structural differences between both series of gemini surfactants result in different aggregation and surface properties for surfactants with 6 and 8 methylene groups in the spacer (N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethylhexane-1,6-diaminium dibromide and N,N’-bis(tridecane-2-yl)-N,N,N’,N’-tetramethyloctane-1,8-diaminium dibromide) with the cmc values 8.2 × 10−4 mol/L and 6.5 × 10−4 mol/L, respectively, as determined by surface tension measurements. Particle size analysis showed the formation of small stable spherical micelles in the interval between 2.8 and 5 nm and with zeta potential around +50 mV, which are independent of surfactant concentration and increase with the increasing spacer length. Microbicidal activity of 13-s-13 gemini surfactants was found to be efficient against Gram-positive, Gram-negative bacteria and yeast.

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Self-aggregation of cationic gemini surfactants with amide groups in the spacer and variable alkyl chain length

Pisárčik,

Bajcura,

Lukáč

et al. 2023

Colloid Polym Sci

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Synthesis, aggregation parameters and antimicrobial activity of novel cationic gemini surfactants with two amide groups in gemini spacer structure and a variable number of carbon atoms in alkyl tails ranging from 12 to 15 are reported. The critical micelle concentration of gemini surfactants was determined using surface tension and electrical conductivity methods. The cmc values were found in the range 0.83 to 0.06 mM. The interfacial area, micelle ionisation degree and the Gibbs free energy per molecule and alkyl chain were calculated from the surface tension and conductivity curves. Particle size analysis using the dynamic light scattering method confirmed the formation of small spherical micelles 6–7 nm large in size for gemini surfactants with 12 and 13 carbon atoms in the alkyl chain. A large size above 50 nm was found for the aggregates composed of long-chain gemini molecules with 14 and 15 carbon atoms. The zeta potential of gemini surfactants shows a continuous increase with the increasing alkyl chain length. Micelle aggregation number of gemini surfactants correlates well with the hydrodynamic size data. Small aggregation number values were found for short-chain gemini molecules with 12 and 13 carbon atoms in the alkyl chain. Long-chain gemini molecules with 14 and 15 carbon atoms exhibit aggregate growth represented by an increase in the aggregation number values while maintaining the spherical or spheroidal shape of micelles. The investigations of antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria and yeast indicate the increasing antimicrobial efficiency towards the short-chain surfactant with 12 carbon atoms in the alkyl chain. A possible cut-off effect presence is proposed to explain the dependence of antimicrobial activity on the surfactant alkyl tail length.

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Effect of the alkyl chain length on micelle formation for bis(N-alkyl-N,N-dimethylethylammonium)ether dibromides

Cited by 20 publications

References 58 publications

Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer

Antimicrobial Activity of Gemini Surfactants with Azapolymethylene Spacer

The Synthesis, Self-Assembled Structures, and Microbicidal Activity of Cationic Gemini Surfactants with Branched Tridecyl Chains

Self-aggregation of cationic gemini surfactants with amide groups in the spacer and variable alkyl chain length

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