Synthesis, Characterization, and Evaluation of Surface Properties of Cyclohexanoxycarbonylmethylpyridinium and Cyclohexanoxycarbonylmethylimidazolium Ionic Liquids

Aggarwal, Rajni; Singh, Sukhprit; Hundal, Geeta

doi:10.1021/ie3020473

Cited by 11 publications

(5 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For both series of amide-functionalized ionic liquids (C n AMeImBr and C n APyrBr) the cmc decreases with increasing the alkyl chain length ( Table 2). This behaviour is analogous to that reported for different functionalized [19,20,26,33] and non-functionalized amphiphilic ILs [14,16,36,37], as well as for ionic surfactants [38][39][40].…”

Section: Conductivity Measurementssupporting

confidence: 86%

“…The plots for the rest of the amide-functionalized ILs studied are given in the Supplementary data (Appendix A). cmc the rate augmentation of the specific conductivity is lower because the micelles can contribute to the charge transport to a lesser extent than the free ions owing to their lower mobility and to the effective loss of ionic charge as a result of the binding of a fraction of counterions to the micellar surface [20,33,34]. The counterion binding parameter (β) gives the extent of counter ion association and can be estimated from the ratio of the slopes above and below the cmc [35].…”

Section: Conductivity Measurementsmentioning

confidence: 99%

See 1 more Smart Citation

Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution

Garcı́a

Ribosa

Pérez

et al. 2014

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

Surface active amide-functionalized ionic liquids (ILs) consisting of a long alkyl chain (C6C14) connected to a polar head group (methylimidazolium or pyridinium cation) via an amide functional group were synthesized and their thermal stability, micellar properties and antimicrobial activity in aqueous solution investigated. The incorporation of an amide group increased the thermal stability of the functionalized ionic liquids compared to simple alkyl chain substituted ionic liquids. The surface activity and aggregation behaviour in aqueous solution of amide-functionalized ionic liquids were examined by tensiometry, conductivity and spectrofluorimetry. Amide-functionalized ILs displayed surface activity and their critical micelle concentration (cmc) in aqueous media decreased with the elongation of the alkyl side chain as occurs for typical surfactants. Compared to non-functionalized ILs bearing the same alkyl chain, ionic liquids with an amide moiety possess higher surface activity (pC20) and lower cmc values. The introduction of an amide group in the hydrophobic chain close to the polar head enhances adsorption at the air/water interface and micellization which could be attributed to the H-bonding in the headgroup region. The antimicrobial activity was evaluated against a panel of representative Gram-negative and Gram-positive bacteria and fungi. Amide-functionalized ILs with more than eight carbon atoms in the side chain showed broad antimicrobial activity. Antibacterial activities were found to increase with the alkyl chain length being the C12 homologous the most effective antimicrobial agents. The introduction of an amide group enhanced significantly the antifungal activity as compared to non-functionalized ILs.

show abstract

Section: Conductivity Measurementssupporting

confidence: 86%

Section: Conductivity Measurementsmentioning

confidence: 99%

Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution

Garcı́a

Ribosa

Pérez

et al. 2014

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

show abstract

“…A recent survey on the value of CMC of different ionic liquids has shown that alteration in the structure of the cationic head group leads to the reduction in the value of CMC. Introduction of different types of functional groups, like, alcohol (Chauhan et al, ), ester (Aggarwal et al, ; Aggarwal and Singh, ), or amide (Kanjilal et al, ), into the cationic head groups affects the value of CMC considerably. The surface tension measurements not only measure the CMC, but also provide many other physicochemical parameters.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Evaluation of Surface and Thermal Properties and Cytotoxicity of 2‐Hydroxy‐3‐Phenoxypropyl Imidazolium Bola‐Type Gemini Amphiphiles

Aggarwal

Singh

Saini

et al. 2018

J Surfact & Detergents

Self Cite

View full text Add to dashboard Cite

A library of imidazolium‐based gemini cationic bola amphiphiles was synthesized using a regioselective ring‐opening reaction of glycidyl phenyl ether with imidazole under solvent‐free conditions. The corresponding hexafluorophosphate (PF6−) and tetrafluoroborate (BF4−) counterion‐containing amphiphiles were also synthesized and characterized using nuclear magnetic resonance (NMR) and mass spectroscopy. The micellar and interfacial parameters like the critical micelle concentration (CMC), surface pressure at the CMC (Пcmc), surface tension at CMC ( γcmc), counterion binding (β), maximum surface excess concentration ( Γmax), minimum area per molecule ( Amin), standard free energy of micellization (normalΔGmic0) and adsorption (normalΔGads0), and Kraft temperature were evaluated using surface tension and conductometry methods in aqueous solution as well as in buffer solution. Dynamic light scattering (DLS) was used to determine the size of the micelles formed in the aqueous solution. Cytotoxicity tests were carried out on the C6 glioma cancerous brain cell line using the MTT assay (3‐(4, 5‐dimethylthiazole‐2‐yl)‐2, 5‐diphenyltetrazolium bromide) to evaluate the IC50 value of all the synthesized amphiphiles. Thermal stability of these amphiphiles was also evaluated using a thermal gravimetric analyzer (TGA). Economic way of synthesis, moderate thermal stability, a low value of CMC, and cytotoxicity of these amphiphiles will inspire new research in the field of nanobiotechnology and pharmaceutical industries.

show abstract

“…[1,2] They manifest interesting physicochemical properties like high thermal stability, high conductivity, negligible low vapor pressure and non-flammability. [3][4][5] A modified form of ILs known as surface-active ionic liquids (SAILs) possessing desirable combined characteristics of both ILs and surfactants have been introduced. [6] Analogous to conventional ionic liquids (ILs), properties of SAILs can be adjusted by selecting the proper cation and anion combination.…”

Section: Introductionmentioning

confidence: 99%

“…Ionic liquids (ILs) are mainly composed of ions (cations and anions) with melting points below 100 °C and have emerged as intriguing substitutes for traditionally used volatile organic solvents [1,2] . They manifest interesting physicochemical properties like high thermal stability, high conductivity, negligible low vapor pressure and non‐flammability [3–5] . A modified form of ILs known as surface‐active ionic liquids (SAILs) possessing desirable combined characteristics of both ILs and surfactants have been introduced [6] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Self‐Aggregation, Interfacial Behavior and Interaction Studies of Non‐ Cytotoxic Caffeinium‐Based Surface Active Ionic Liquids with Sodium Dodecyl Sulfate

et al. 2022

View full text Add to dashboard Cite

Caffeinium-based surface-active ionic liquids (SAILs), (1-(2alkanoyl oxy) ethylcaffeinium bromide), [C n Ecaf]Br with variable chain length (n = 12, 14, 16) were synthesized and their molecular structures were explored by multiple spectral techniques. The critical micelle concentration (CMC) of pure SAILs and their mixtures with sodium dodecyl sulfate (SAIL-DS) in aqueous solution was determined by employing various techniques at 298 K. The tensiometry and dynamic light scattering (DLS) techniques have been employed to gain insight about the interfacial behavior and aggregate size of catanionic mixtures in aqueous solution. Interestingly, the interaction parameters (X m 1 ; b m ) showed strong synergism between these two oppositely charged molecules. Further, it was found that SAIL-DS cat-anionic mixtures exhibit excellent adsorption efficacy and are more effective in lowering the surface tension of water as compared to pure SAILs. The DLS results showed the formation of mixed-size aggregates in SAIL-DS systems. The contact angle and wetting properties of pure SAILs over the parafilm surface were also determined using a static sessile drop method. Further, MTT assay was used to determine the biocompatibility of SAILs on Human embryonic kidney (HEK-293) cell line and in-vitro anti-cancer activity on Lung cancer cells (A549). These SAILs displayed substantial cytotoxicity against cancerous cells, indicating that they could be useful in a variety of biological applications.

show abstract

Synthesis, Characterization, and Evaluation of Surface Properties of Cyclohexanoxycarbonylmethylpyridinium and Cyclohexanoxycarbonylmethylimidazolium Ionic Liquids

Cited by 11 publications

References 43 publications

Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution

Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution

Synthesis, Characterization, and Evaluation of Surface and Thermal Properties and Cytotoxicity of 2‐Hydroxy‐3‐Phenoxypropyl Imidazolium Bola‐Type Gemini Amphiphiles

Synthesis, Self‐Aggregation, Interfacial Behavior and Interaction Studies of Non‐ Cytotoxic Caffeinium‐Based Surface Active Ionic Liquids with Sodium Dodecyl Sulfate

Contact Info

Product

Resources

About