Tris-imidazolium and benzimidazolium ionic liquids: a new class of biodegradable surfactants

Al-Mohammed, Nassir N.; Hussen, Rusnah Syahila Duali; Alias, Yatimah; Abdullah, Zanariah

doi:10.1039/c4ra14027c

Cited by 43 publications

(35 citation statements)

References 59 publications

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“…64, using the CBT (OECD 301D) was reported in 2015 by Al-Mohammed et al 15,16 As can be seen from Fig. 64, using the CBT (OECD 301D) was reported in 2015 by Al-Mohammed et al 15,16 As can be seen from Fig.…”

Section: Biodegradable Surfactants: An Il By Another Namementioning

confidence: 89%

“…9. 51 Alkyl substituted imidazolium (8,13), pyridinium (16,17) and dimethylamino-pyridinum (18-20) ILs were not found to be readily anaerobically biodegradable compounds under the studies test conditions (Table 9). Attempts to induce biodegradation by co-metabolism through the addition of an acetate salt failed.…”

Section: Biodegradation Of Ils Under Denitrifying Conditionsmentioning

confidence: 97%

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Biodegradation of ionic liquids – a critical review

2015

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The importance of biodegradation data as part of the design of safer chemicals is presented using ionic liquids (ILs) as a model study. Structural features that promote/impede IL biodegradation, IL design strategies, methods of biodegradation analysis, properties of IL/surfactant derivatives and computational methods of predicting biodegradation are discussed. The importance of metabolite studies as part of biodegradation assays is highlighted. The relevance of applying the lessons learned developing biodegradable ILs to other chemical classes is proposed. A comprehensive appendix of IL biodegradation data published since 2010 (∼300 ILs) has been compiled.

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Section: Biodegradable Surfactants: An Il By Another Namementioning

confidence: 89%

Section: Biodegradation Of Ils Under Denitrifying Conditionsmentioning

confidence: 97%

Biodegradation of ionic liquids – a critical review

2015

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“…The majority of these ILs showed significant antibacterial activity towards most of the selected microorganisms as shown in Figure 2. [69][70][71][72][73] Due to the similarity of ILs structure to detergents, pesticides and antibiotics, the proposed mechanism of ILs toxicity is through membrane disruption where the toxic effect may be related to a common cellular structure or process. 37,63,64 Therefore, the presence of incorporated benzenesulfonamide moiety adjacent to the imidazolium and benzimidazolium core ILs, successfully promoted the antibacterial activity of the produced geminal dicationic ILs.…”

Section: Antibacterial Activitiesmentioning

confidence: 99%

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

2015

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Based on bis-imidazolium and benzimidazolium, new sets of geminal dicationic ionic liquids containing sulphonamide moiety were successfully synthesized with good yields. Their structures were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, and mass spectroscopy. Selected physicochemical properties of these ILs including; thermal stability by TGA and miscibility in some common organic solvents and water were also determined. Most of the prepared dicationic ILs displayed significant level of antibacterial activities against ten selected bacterial strains of Gram-positive and Gram-negative using micro-broth dilution assay. ͞ calcd. for C 29 H 42 N 5 O 6 S 3+ : 588.2856, found: 588.2919; m/z, [NTF 2 ] ͞ calcd. for C 2 F 6 NO 4 S 2 − : 279.9173, found: 279.9145. N,N-bis[(3-allyl-benzimidazol-1-iumyl)ethyl]-4-methylbenzenesulphonamide-bis(trifluorometh- ylsulphonyl)amide (8a)This compound was prepared analogously to 7d using N, N-bis[(3-allyl-benzimidazol-1-iumyl) ethyl]-4-methylbenzenesulphonamide bromide 6a (0.7 g, 1.0 mmole) and Lithium bis-(trifluoromethanesulphonyl)imide LiNTf 2 (0.72 g, 2.5 mmol) to provide a clear viscous hygroscopic liquid at room temperature in 90% yield (1 g). Ten standard strains of Gram positive and negative bacteria were used to evaluate the antibacterial activities of the synthesized ILs compounds; 5a-f and 6a-f. Based on CLSI guidelines 85 , the activities were assessed in terms of minimum inhibitory concentrations (MICs) using microbroth dilution assays. The MIC's values are given in mg/mL and defined as a lowest concentration that inhibits the bacterial strains growth. Gram positive bacteria included: Streptococcus pyogenes ATCC19615, Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC6051, Rodococcus Ruber ATCC27863, Enterococcus faecalis ATCC 29212, Staphylococcus epidermidis ATCC12228, while Gram negative bacteria included: Escherichia coli ATCC10538, Salmonella typhimurium ATCC14028, Pseudomonas aeruginosa ATCC15442, Acinetobacter calcoaceticus ATCC 23055. These standards strains were obtained from the collection Distilled water was used as negative control to dissolve all the tested ILs in concentrations range of 0.05-0.5 mg/mL, while, commercial antibiotics amoxicillin and kanamycin were used as a positive control in the same range of concentrations. A loopful of bacterial cells from the nutrient agar plates ofThe incorporated benzenesulfonamide moiety and the active side substituents into diimidazolium and benzimidazolium cations enhanced both antibacterial activity and miscibility for the synthesized gimini type ILs.

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“…1-butylbenzimidazole (BBIm) was prepared as described previously. [53] For preparation of BHBImI, a 100 mL round bottom flask equipped with a stirring bar was charged with BBIm (6.56 g, 37.6 mmol), hexyl iodide (13.87 mL, 94.1 mmol, 19.95 g), and 10 mL tetrahydrofuran. The solution was heated to reflux with stirring and cooled after 16 h. Once cooled at room temperature, the crude mixture was cooled, it was concentrated on a rotary evaporator to yield a pale yellow oil that crystallized upon standing (14.2 g, 36.8 mmol, 98% yield).…”

Section: Methodsmentioning

confidence: 99%

Effective Preparation of Nanoscale CH₃NH₃PbI₃ Perovskite Photosensitizers for Mesoporous TiO₂‐Based Solar Cells by Successive Precursor Layer Adsorption and Reaction Process

et al. 2019

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Nanoscale CH3NH3PbI3 perovskite sensitizers are grown by delivering each precursor successively onto the surface of mesoporous (meso) TiO2 electrodes. Using Pb(NO3)2 ions as a lead(II) source and CH3NH3I (MAI) for methylammonium and iodide sources, repetitive cycles of the two dipping steps are successful in growing few nanometer‐sized MAPbI3 gradually on the TiO2 surface inside the meso‐TiO2 film. However, some aggregates are observed on the top surface of the meso‐TiO2 film due to slight dissolution of PbI2 and its accumulation/reaction with MAI at the top surface of the meso‐TiO2 film. To solve this inhomogeneity of the deposition, a nondestructive multiple deposition route for nanoscale MAPbI3 is suggested as a successive precursor layer adsorption and reaction (SPLAR) process where, from the second cycle of deposition, PbI2 is delivered with the help of an ionic liquid compound dissolved in dichloromethane. With this new Pb precursor in less‐polar solvents, nanoscale MAPbI3 sensitizers are grown without dissolution of preformed perovskites or formation of some aggregates at the top surface. After the third cycle of SPLAR deposition, about 7.0 nm–sized MAPbI3 sensitizers are prepared and display enhanced photovoltaic performance (7.18 ± 0.31%) compared with devices obtained from only one cycle (5.74 ± 0.30%).

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Tris-imidazolium and benzimidazolium ionic liquids: a new class of biodegradable surfactants

Abstract: Factors that improved the biodegradation of surfactants have successfully used to prepare higher ordered biodegradable tris-imidazolium and benzimidazolium ionic liquids.

Cited by 43 publications

References 59 publications

Biodegradation of ionic liquids – a critical review

Biodegradation of ionic liquids – a critical review

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

Effective Preparation of Nanoscale CH₃NH₃PbI₃ Perovskite Photosensitizers for Mesoporous TiO₂‐Based Solar Cells by Successive Precursor Layer Adsorption and Reaction Process

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Tris-imidazolium and benzimidazolium ionic liquids: a new class of biodegradable surfactants

Abstract: Factors that improved the biodegradation of surfactants have successfully used to prepare higher ordered biodegradable tris-imidazolium and benzimidazolium ionic liquids.

Cited by 43 publications

References 59 publications

Biodegradation of ionic liquids – a critical review

Biodegradation of ionic liquids – a critical review

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

Effective Preparation of Nanoscale CH3NH3PbI3 Perovskite Photosensitizers for Mesoporous TiO2‐Based Solar Cells by Successive Precursor Layer Adsorption and Reaction Process

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Effective Preparation of Nanoscale CH₃NH₃PbI₃ Perovskite Photosensitizers for Mesoporous TiO₂‐Based Solar Cells by Successive Precursor Layer Adsorption and Reaction Process