Effect of counterions on the micellization and monolayer behaviour of cationic gemini surfactants

Islam, Md. Saiful; Shortall, Samantha Marisha; Mekhail, George M.; Callender, Shannon P.; Madkhali, Osama A.; Bharwani, Zameer; Ayyash, D.; Kobernyk, Katherine; Wettig, Shawn D.

doi:10.1039/c7cp00775b

Cited by 18 publications

(10 citation statements)

References 82 publications

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“…There are several factors influencing the value of CMC of cationic GS, such as the following: temperature, chemical structure, and the presence of other substances in the solution [ 1 ]. Construction elements affecting CMC values are the length or nature of the spacer [ 68 , 81 , 82 , 83 , 84 , 85 , 86 , 87 ] and the kind of counter ion [ 69 , 88 , 89 ]. However, the length of hydrocarbon substituent affects the greatest impact on surface activity [ 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 ].…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

et al. 2021

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Due to their large possibility of the structure modification, alkylammonium gemini surfactants are a rapidly growing class of compounds. They exhibit significant surface, aggregation and antimicrobial properties. Due to the fact that, in order to achieve the desired utility effect, the minimal concentration of compounds are used, they are in line with the principle of greenolution (green evolution) in chemistry. In this study, we present innovative synthesis of the homologous series of gemini surfactants modified at the spacer by the ether group, i.e., 3-oxa-1,5-pentane-bis(N-alkyl-N,N-dimethylammonium bromides). The critical micelle concentrations were determined. The minimal inhibitory concentrations of the synthesized compounds were determined against bacteria Escherichia coli ATCC 10536 and Staphylococcus aureus ATCC 6538; yeast Candida albicans ATCC 10231; and molds Aspergillus niger ATCC 16401 and Penicillium chrysogenum ATCC 60739. We also investigated the relationship between antimicrobial activity and alkyl chain length or the nature of the spacer. The obtained results indicate that the synthesized compounds are effective microbicides with a broad spectrum of biocidal activity.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

et al. 2021

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“…However, the cmc values are lower than those reported for pyridinium, ammonium and imidazolium gemini surfactants (Asadov et al, 2019; Patial et al, 2014; Shaheen et al, 2020; Yao et al, 2013). The lower cmc values of the series 3a – c are attributed to the presence of ester functionalities in their tail groups in addition to the imidazolium head groups (Bhadani et al, 2015; Islam et al, 2017; Kabir‐ud‐Din et al, 2010; Patial et al, 2013; Zhuang et al, 2013). The high flexibility and closer arrangement of ester‐bonded gemini surfactant molecules results in lower cmc and better aggregation ability of 3a – c .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, micellization and cytotoxic studies of ester‐functionalized imidazolium gemini surfactants

Mir

Shaheen

Wani

et al. 2021

J Surfact & Detergents

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The fatty acid-based imidazolium gemini surfactants containing hydroxysubstituted spacers were synthesized and characterized by different spectral techniques. The micellization behavior of product compounds was studied by determining their critical micelle concentration (cmc) values from steady state fluorescence and conductivity measurements. The thermodynamic parameters of micellization of synthesized gemini surfactants confirmed that the micelle formation is a thermodynamically favorable, endothermic and an entropy driven phenomenon. The surfactants were further analyzed for their cytotoxic nature by treating them upon human embryonic kidney cell (HEK-293) line and were found to be significantly low cytotoxic. The interesting features like low cmc values, non-cytotoxic and eco-friendly nature of the gemini surfactants may offer new and more efficient substitutes to the conventional drug delivery systems. Thus the gemini surfactants may serve as promising candidates in the biomedical and pharmaceutical fields.

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“…The conductivity values of CPCl and CPBr at all the studied compositions of PrOH–WR mixed media at 298.15 K are listed in Tables S1 and S2 (Supporting Information). The difference in their conductivity values of two systems could be due to different electrostatic affinity of their counterions (Cl – and Br – ) with the cationic micellar system of the surfactant, change in the rheology of the liquid state (especially viscosity) and variation in the dielectric constant values of corresponding mixed media caused by an increase in vol %. , Dielectric constant of pure water (ε WR = 80.1) is relatively much higher than that of pure PrOH (ε PrOH = 20.18) at 293.2 K . Reduction of ε with an increase in vol % of PrOH of resultant mixed media can be the prominent reason to provide different solvophobic tendencies of the surfactant molecules to undergo self-assembly in the corresponding compositions of the mixed media.…”

Section: Resultsmentioning

confidence: 99%

Micellar Solution Behavior of Cetylpyridinium Surfactants in 2-Propanol–Water Mixed Media at Different Temperatures

2020

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Self-assembly of surfactant systems in organic solvent–water mixed media is relevant in several industrial and pharmaceutical applications. This article emphasizes the role of 2-propanol (PrOH) as a cosolvent in the micellization of cetylpyridinium chloride (CPCl) and cetylpyridinium bromide (CPBr) surfactants at different temperatures (293.15–308.15 K) studied through the conductometric technique. The results show an enhancement in CMC values for both the surfactants with an increase in volume percentage (vol %) of PrOH (from 0 up to 20 vol %) as well as temperature. The CPBr shows distinct behavior in the lower composition of PrOH–WR (0 and 2.5%) at a higher temperature (308.15 K). The rise in the CMC values depends on lowering of permittivity of the mixed media caused by change in compositions of PrOH–WR mixed media. A similar effect is also seen on the degree of counterion dissociation (α) values with an exception to a few compositions. The increase in α values is found to be relatively less for CPBr as compared to CPCl. Temperature dependency of CMC values has been used to calculate thermodynamic parameters such as the change in Gibbs energy (ΔG m 0), enthalpy (ΔH m 0), and entropy (ΔS m 0) of micellization, and their values were used to analyze the effect of various compositions of PrOH–WR mixed media. The ΔG m 0 values indicate that micellization is spontaneous and becomes less favorable with the inclusion of PrOH. The values of ΔH m 0(<0) and ΔS m 0(>0) affirm that the process of micellization is entropically driven within the scope of the studied temperature. Overall results have been analyzed based on the interactions between the solute and solvent, counterions and aggregates, and solvation/desolvation of counterions.

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Effect of counterions on the micellization and monolayer behaviour of cationic gemini surfactants

Cited by 18 publications

References 82 publications

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

Antimicrobial Activity of Gemini Surfactants with Ether Group in the Spacer Part

Synthesis, micellization and cytotoxic studies of ester‐functionalized imidazolium gemini surfactants

Micellar Solution Behavior of Cetylpyridinium Surfactants in 2-Propanol–Water Mixed Media at Different Temperatures

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