{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T07:38:20Z","timestamp":1774597100157,"version":"3.50.1"},"reference-count":70,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2024,12,5]],"date-time":"2024-12-05T00:00:00Z","timestamp":1733356800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Science and Higher Education in Poland","award":["0912\/SBAD\/2408"],"award-info":[{"award-number":["0912\/SBAD\/2408"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study investigates a series of surface-active ionic liquids (SAILs), including both imidazolium monocationic and dicationic compounds. These compounds are promising candidates, as they combine unique surface properties with antimicrobial activity, aligning with modern trends in chemistry. The research encompasses synthesis, thermal analysis, and topographical assessment, focusing on the impact of the amphiphilic cationic moiety, alkyl chain length, and the spatial relationship between the imidazolium ring and the phenyl substituent on the compounds\u2019 physicochemical behavior. An added value of this work lies in the integration of theoretical calculations related to their behavior in solution and at the air\u2013water interface, revealing spontaneous adsorption (negative Gibbs free energy of adsorption values, \u0394G0ads). The results indicate that dicationic imidazolium SAILs have a greater tendency to form micelles but are less effective at reducing surface tension compared to their monocationic counterparts. Topography analyses of SAILs with 12 carbon atoms further highlight these differences. Notably, the dicationic SAIL with 12 carbon atoms in the spacer exhibited an impressive MIC of 0.007 mmol L\u22121 against Candida albicans, consistent with findings showing that dicationic SAILs outperformed conventional antifungal agents, such as amphotericin B and fluconazole, at equivalent concentrations. Overall, the synthesized SAILs demonstrate superior surface activity compared to commercial surfactants and show potential as disinfectant agents.<\/jats:p>","DOI":"10.3390\/molecules29235743","type":"journal-article","created":{"date-parts":[[2024,12,5]],"date-time":"2024-12-05T06:24:44Z","timestamp":1733379884000},"page":"5743","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Impact of Alkyl Spacer and Side Chain on Antimicrobial Activity of Monocationic and Dicationic Imidazolium Surface-Active Ionic Liquids: Experimental and Theoretical Insights"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0385-6886","authenticated-orcid":false,"given":"Marta","family":"Wojcieszak","sequence":"first","affiliation":[{"name":"Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2607-5812","authenticated-orcid":false,"given":"Sylwia","family":"Zi\u0119ba","sequence":"additional","affiliation":[{"name":"Department of Molecular Crystals, Institute of Molecular Physics Polish Academy of Sciences, Smoluchowskiego 17, 60-179 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2594-8386","authenticated-orcid":false,"given":"Alina T.","family":"Dubis","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bialystok, Cio\u0142kowskiego 1K, 15-245 Bia\u0142ystok, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9006-0549","authenticated-orcid":false,"given":"Maciej","family":"Karolak","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology, Faculty of Pharmacy, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8219-6339","authenticated-orcid":false,"given":"\u0141ukasz","family":"Pa\u0142kowski","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology, Faculty of Pharmacy, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8299-5085","authenticated-orcid":false,"given":"Agnieszka","family":"Marcinkowska","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrzej","family":"Skrzypczak","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-2389-704X","authenticated-orcid":false,"given":"Alicja","family":"Putowska","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6169-4152","authenticated-orcid":false,"given":"Katarzyna","family":"Materna","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Pozna\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"118160","DOI":"10.1016\/j.molliq.2021.118160","article-title":"Surface-Active Ionic Liquids: A Review","volume":"347","author":"Buettner","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"121300","DOI":"10.1016\/j.molliq.2023.121300","article-title":"Evaluation of Antimicrobial Properties of Monocationic and Dicationic Surface-Active Ionic Liquids","volume":"374","author":"Wojcieszak","year":"2023","journal-title":"J. Mol. Liq."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1016\/j.jcis.2008.04.011","article-title":"Surface-Active, Micellar, and Antielectrostatic Properties of Bis-Ammonium Salts","volume":"323","author":"Chlebicki","year":"2008","journal-title":"J. Colloid Interface Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"112303","DOI":"10.1016\/j.chemphys.2024.112303","article-title":"Surface-Active Ionic Liquids as Drug Carriers: A Physico-Chemical Study","volume":"583","author":"Asghar","year":"2024","journal-title":"Chem. Phys."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1016\/j.colsurfb.2018.12.010","article-title":"Self-Assembling and Biological Properties of Single-Chain Dicationic Pyridinium-Based Surfactants","volume":"175","author":"Kashapov","year":"2019","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Ali, M.K., Moshikur, R.M., and Goto, M. (2021). Surface-Active Ionic Liquids for Medical and Pharmaceutical Applications. Application of Ionic Liquids in Drug Delivery, Springer.","DOI":"10.1007\/978-981-16-4365-1_9"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"125219","DOI":"10.1016\/j.molliq.2024.125219","article-title":"Aromatic Salt Induced Modulations in Micellization Behavior of Amide Functionalized Surface-Active Ionic Liquids: The Role of Cationic Head Group","volume":"407","author":"Kaur","year":"2024","journal-title":"J. Mol. Liq."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"116353","DOI":"10.1016\/j.molliq.2021.116353","article-title":"Cation Isomerism Effect on Micellization of Pyridinium Based Surface-Active Ionic Liquids","volume":"337","author":"Tot","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1016\/j.jhazmat.2015.05.034","article-title":"Novel Surface-Active Ionic Liquids Used as Solubilizers for Water-Insoluble Pesticides","volume":"297","author":"Fan","year":"2015","journal-title":"J. Hazard. Mater."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1016\/j.jcis.2007.04.028","article-title":"Synthesis and Micellar Properties of Surface-Active Ionic Liquids: 1-Alkyl-3-Methylimidazolium Chlorides","volume":"313","author":"Pires","year":"2007","journal-title":"J. Colloid Interface Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1002\/cphc.201801127","article-title":"Synthesis and Characterization of Surface-Active Ionic Liquids Used in the Disruption of Escherichia coli Cells","volume":"20","author":"Sintra","year":"2019","journal-title":"ChemPhysChem"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1016\/j.colsurfa.2007.02.012","article-title":"Interfacial and Micellar Properties of Imidazolium-Based Monocationic and Dicationic Ionic Liquids","volume":"302","author":"Baltazar","year":"2007","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"224","DOI":"10.1016\/j.colsurfa.2015.01.026","article-title":"Interfacial and Aggregation Behavior of Dicationic and Tricationic Ionic Liquid-Based Surfactants in Aqueous Solution","volume":"469","author":"Nacham","year":"2015","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2453","DOI":"10.1021\/je2000183","article-title":"Comparison between Dicationic and Monocationic Ionic Liquids: Liquid Density, Thermal Properties, Surface Tension, and Shear Viscosity","volume":"56","author":"Shirota","year":"2011","journal-title":"J. Chem. Eng. Data"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2901","DOI":"10.1007\/s00396-015-3680-y","article-title":"Anion Effect on the Aggregation Behavior of the Long-Chain Spacers Dicationic Imidazolium-Based Ionic Liquids","volume":"293","author":"Frizzo","year":"2015","journal-title":"Colloid Polym. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1039\/b921805j","article-title":"Antimicrobial and Surface Activity of 1-Alkyl-3-Methylimidazolium Derivatives","volume":"12","author":"Jungnickel","year":"2010","journal-title":"Green Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"6511","DOI":"10.1021\/acs.langmuir.7b00505","article-title":"Micellization and Antimicrobial Properties of Surface-Active Ionic Liquids Containing Cleavable Carbonate Linkages","volume":"33","author":"Garcia","year":"2017","journal-title":"Langmuir"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"109907","DOI":"10.1016\/j.msec.2019.109907","article-title":"Comparative Evaluation of Antimicrobial Activity of Different Types of Ionic Liquids","volume":"104","author":"Florio","year":"2019","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"873","DOI":"10.1039\/c3nj40759d","article-title":"Enhanced Antimicrobial Activities of 1-Alkyl-3-Methyl Imidazolium Ionic Liquids Based on Silver or Copper Containing Anions","volume":"37","author":"Gilmore","year":"2013","journal-title":"New J. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"10504","DOI":"10.1021\/acsami.7b00387","article-title":"Synthesis of Pyrrolidinium-Type Poly(Ionic Liquid) Membranes for Antibacterial Applications","volume":"9","author":"Qin","year":"2017","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8385","DOI":"10.1021\/acs.jpcb.7b03525","article-title":"Thermodynamic Insights into the Binding of Mono- and Dicationic Imidazolium Surfactant Ionic Liquids with Methylcellulose in the Diluted Regime","volume":"121","author":"Ziembowicz","year":"2017","journal-title":"J. Phys. Chem. B"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"12171","DOI":"10.1007\/s10853-021-06055-1","article-title":"Effect of Dicationic Ionic Liquids on Cloud Points of Tergitol Surfactant and the Formation of Aqueous Micellar Two-Phase Systems","volume":"56","author":"Bender","year":"2021","journal-title":"J. Mater. Sci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"136","DOI":"10.1016\/j.jiec.2014.11.025","article-title":"Effect of Alkyl-Chain Length of Imidazolium Based Ionic Liquid on Ion Conducting and Interfacial Properties of Organic Electrolytes","volume":"26","author":"Kim","year":"2015","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"114172","DOI":"10.1016\/j.molliq.2020.114172","article-title":"Influence of Lipophilic Tail and Linker Groups on the Surface and Thermal Properties of the Synthesized Dicationic Surfactants for Oilfield Applications","volume":"319","author":"Hussain","year":"2020","journal-title":"J. Mol. Liq."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"30154","DOI":"10.1039\/C9RA06577F","article-title":"Surface and Thermal Properties of Synthesized Cationic Poly(Ethylene Oxide) Gemini Surfactants: The Role of the Spacer","volume":"9","author":"Hussain","year":"2019","journal-title":"RSC Adv."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"11664","DOI":"10.1021\/jp9535598","article-title":"Role of Spacer Chain Length in Dimeric Micellar Organization. Small Angle Neutron Scattering and Fluorescence Studies","volume":"100","author":"De","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"7170","DOI":"10.1021\/la050952o","article-title":"Synthesis and Properties of Cationic Oligomeric Surfactants","volume":"21","author":"Laschewsky","year":"2005","journal-title":"Langmuir"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"469","DOI":"10.1007\/s00396-004-1219-8","article-title":"Spacer Effects in Dimeric Cationic Surfactants","volume":"283","author":"Laschewsky","year":"2005","journal-title":"Colloid Polym. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/j.jiec.2017.10.018","article-title":"Cationic Gemini Surfactants Containing an O-Substituted Spacer and Hydroxyethyl Moiety in the Polar Heads: Self-Assembly, Biodegradability and Aquatic Toxicity","volume":"59","author":"Kaczerewska","year":"2018","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1016\/j.colsurfa.2015.08.012","article-title":"Aggregation Behavior of Anionic Sulfonate Gemini Surfactants with Dodecylphenyl Tails","volume":"484","author":"Woch","year":"2015","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.colsurfa.2012.01.006","article-title":"Preparation, Characterization and Properties of Anionic Gemini Surfactants with Long Rigid or Semi-Rigid Spacers","volume":"397","author":"Zhu","year":"2012","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"16682","DOI":"10.1021\/jp8069089","article-title":"Structural Effects of Anions and Cations on the Aggregation Behavior of Ionic Liquids in Aqueous Solutions","volume":"112","author":"Wang","year":"2008","journal-title":"J. Phys. Chem. B"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"26040","DOI":"10.1039\/C4CP04054F","article-title":"Effect of Cationic Head Group on Micellization Behavior of New Amide-Functionalized Surface Active Ionic Liquids","volume":"16","author":"Kamboj","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1092","DOI":"10.1021\/acs.jpcb.5b09688","article-title":"Micellization Behavior of Surface Active Ionic Liquids Having Aromatic Counterions in Aqueous Media","volume":"120","author":"Singh","year":"2016","journal-title":"J. Phys. Chem. B"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1016\/j.molliq.2017.05.116","article-title":"Self-Assembly of Imidazolium-Based Surface Active Ionic Liquids in Aqueous Solution: The Role of Different Substituent Group on Aromatic Counterions","volume":"240","author":"Ma","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"25582","DOI":"10.1021\/acsomega.0c02438","article-title":"The Role of Imidazolium-Based Surface-Active Ionic Liquid to Restrain the Excited-State Intramolecular H-Atom Transfer Dynamics of Medicinal Pigment Curcumin: A Theoretical and Experimental Approach","volume":"5","author":"Rani","year":"2020","journal-title":"ACS Omega"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/j.colsurfa.2008.07.012","article-title":"Self-Organization of Imidazolium Ionic Liquids in Aqueous Solution","volume":"329","author":"Hupka","year":"2008","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"125725","DOI":"10.1016\/j.molliq.2024.125725","article-title":"Effect of Ether Chain and Isomerism on Surface and Antimicrobial Activity of Mono- and Dicationic Imidazolium-Based Surface-Active Ionic Liquids","volume":"411","author":"Wojcieszak","year":"2024","journal-title":"J. Mol. Liq."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3479","DOI":"10.1002\/chem.200400075","article-title":"Ionic Liquids with Symmetrical Dialkoxymethyl-Substituted Imidazolium Cations","volume":"10","author":"Pernak","year":"2004","journal-title":"Chem.-Eur. J."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"34782","DOI":"10.1039\/D3RA07127H","article-title":"Quaternary Ammonium Salts Based on Caprylic Acid as Antimicrobial and Surface-Active Agents","volume":"13","author":"Wojcieszak","year":"2023","journal-title":"RSC Adv."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1515\/tsd-2022-2431","article-title":"Surface Properties of Dicationic Ionic Liquids and Correlation with Biological Activity","volume":"59","author":"Wojcieszak","year":"2022","journal-title":"Tenside Surfactants Deterg."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"8145","DOI":"10.1021\/jp203204c","article-title":"Surfactant Self-Assembly Nanostructures in Protic Ionic Liquids","volume":"115","author":"Carrete","year":"2011","journal-title":"J. Phys. Chem. B"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Rosen, M.J. (2004). Surfactants and Interfacial Phenomena, John Wiley & Sons, Inc.","DOI":"10.1002\/0471670561"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"38470","DOI":"10.1039\/C8RA07081D","article-title":"Clear Distinction between CAC and CMC Revealed by High-Resolution NMR Diffusometry for a Series of Bis-Imidazolium Gemini Surfactants in Aqueous Solutions","volume":"8","author":"Szutkowski","year":"2018","journal-title":"RSC Adv."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Yuli, I., Tzafrir, I., and Salama, P. (2023). Compatibility Investigation of Cationic Surfactants with Anionic Species. Cosmetics, 10.","DOI":"10.3390\/cosmetics10020045"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/j.jcis.2005.12.029","article-title":"Characterization of Micelle Formation of Dodecyldimethyl-N-2-Phenoxyethylammonium Bromide in Aqueous Solution","volume":"298","author":"Khatua","year":"2006","journal-title":"J. Colloid Interface Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/S0021-9797(03)00694-5","article-title":"Physicochemical Properties of Quaternary Ammonium Bromide-Type Trimeric Surfactants","volume":"267","author":"Yoshimura","year":"2003","journal-title":"J. Colloid Interface Sci."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.colsurfa.2014.11.031","article-title":"Synthesis, Surface Activity and Aggregation Behavior of Gemini Imidazolium Surfactants 1,3-Bis(3-Alkylimidazolium-1-Yl) Propane Bromide","volume":"467","author":"Ren","year":"2015","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1016\/j.jcis.2008.06.048","article-title":"Synthesis and Properties of Ionic Liquid-Type Gemini Imidazolium Surfactants","volume":"326","author":"Ao","year":"2008","journal-title":"J. Colloid Interface Sci."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"33256","DOI":"10.1039\/C8RA06217J","article-title":"Synthesis, Surface Activities, and Aggregation Behavior of Phenyl-Containing Carboxybetaine Surfactants","volume":"8","author":"Gao","year":"2018","journal-title":"RSC Adv."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"36015","DOI":"10.1039\/C8RA06900J","article-title":"The Adsorption and Aggregation Properties of Dendritic Cationic Tetrameric Surfactants","volume":"8","author":"Xie","year":"2018","journal-title":"RSC Adv."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1016\/j.crci.2019.04.002","article-title":"Effect of the Alkyl Chain Length on Micelle Formation for Bis(N-Alkyl-N,N-Dimethylethylammonium)Ether Dibromides","volume":"22","author":"Brycki","year":"2019","journal-title":"Comptes Rendus Chim."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2062","DOI":"10.1021\/la9910576","article-title":"Gemini Surfactants with Acetylenic Spacers","volume":"16","author":"Menger","year":"2000","journal-title":"Langmuir"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1515\/tsd-1985-220105","article-title":"Relationship Between Critical Micelle Concentrations and Minimum Inhibitory Concentrations for Some Non-Aromatic Quaternary Ammonium Salts and Amine Oxides","volume":"22","author":"Devinsky","year":"1985","journal-title":"Tenside Surfactants Deterg."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/j.ejpe.2017.05.006","article-title":"4-Aminoantipyrine Derived Cationic Surfactants: Synthesis, Characterization, Surface Activity and Screening for Potential Antimicrobial Activities","volume":"27","author":"Aiad","year":"2018","journal-title":"Egypt. J. Pet."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.jcis.2012.09.073","article-title":"Surface Adsorption and Micelle Formation of Imidazolium-Based Zwitterionic Surface Active Ionic Liquids in Aqueous Solution","volume":"391","author":"Wang","year":"2013","journal-title":"J. Colloid Interface Sci."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2063","DOI":"10.1080\/01932691.2019.1650755","article-title":"Synthesis, Colloidal-Chemical and Petroleum Collecting Properties of New Counterion Coupled Gemini Surfactants Based on Hexadecylbis(2-Hydroxypropyl)Amine and Dicarboxylic Acids","volume":"41","author":"Asadov","year":"2019","journal-title":"J. Dispers. Sci. Technol."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.colsurfa.2010.04.037","article-title":"Adsorption of Poly-2-(Dimethylamino) Ethylmethacrylate-N-Alkyl Quaternized at the Water\/Chloroform Interface","volume":"364","author":"Sagredo","year":"2010","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"124388","DOI":"10.1016\/j.ijpharm.2024.124388","article-title":"Dual Function Surfactants for Pharmaceutical Formulations: The Case of Surface Active and Antibacterial 1-Tolyl Alkyl Biguanide Derivatives","volume":"661","author":"Perinelli","year":"2024","journal-title":"Int. J. Pharm."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Banjare, and Kumar, M (2020). Interfacial and Thermodynamic Approach of Surfactants with \u03b1-Chymotrypsin and Trypsin: A Comparative Study. Indian J. Chem.-Section A, 59, 1128\u20131135.","DOI":"10.56042\/ijca.v59i8.34289"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1007\/s11743-012-1359-7","article-title":"Synthesis and Surface Activities of Amidobetaine Surfactants with Ultra-Long Unsaturated Hydrophobic Chains","volume":"15","author":"Feng","year":"2012","journal-title":"J. Surfactants Deterg."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"10083","DOI":"10.1021\/ja00075a025","article-title":"Gemini Surfactants: A New Class of Self-Assembling Molecules","volume":"115","author":"Menger","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"128","DOI":"10.2174\/1573406410666140902110452","article-title":"Design, Synthesis and Biological Evaluation of Some New Coumarin Derivatives as Potential Antimicrobial Agents","volume":"11","author":"Singh","year":"2015","journal-title":"Med. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1007\/s11743-016-1830-y","article-title":"A Comprehensive Study on the Synthesis and Micellization of Disymmetric Gemini Imidazolium Surfactants","volume":"19","author":"Zhao","year":"2016","journal-title":"J. Surfactants Deterg."},{"key":"ref_65","doi-asserted-by":"crossref","unstructured":"Pham-Truong, T.N., Ghilane, J., and Randriamahazaka, H. (2018). CHAPTER 8: Redox-Active Immobilized Ionic Liquids. Polymerized Ionic Liquids, Royal Society of Chemistry. RSC Smart Materials.","DOI":"10.1039\/9781788010535-00225"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.ijpharm.2018.05.021","article-title":"Characterization and Cytotoxicity Evaluation of Biocompatible Amino Acid Esters Used to Convert Salicylic Acid into Ionic Liquids","volume":"546","author":"Moshikur","year":"2018","journal-title":"Int. J. Pharm."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2000102","DOI":"10.1002\/minf.202000102","article-title":"Estimation of Ionic Liquids Toxicity against Leukemia Rat Cell Line IPC-81 Based on the Empirical-like Models Using Intuitive and Explainable Fingerprint Descriptors","volume":"39","author":"Wu","year":"2020","journal-title":"Mol. Inform."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/0001-8686(96)00295-3","article-title":"Cut-off Effects in Biological Activities of Surfactants","volume":"66","year":"1996","journal-title":"Adv. Colloid. Interface Sci."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"868","DOI":"10.1016\/j.carbpol.2010.08.075","article-title":"Enhancing Antibacterial Activity of Chitosan Surface by Heterogeneous Quaternization","volume":"83","author":"Vallapa","year":"2011","journal-title":"Carbohydr. Polym."},{"key":"ref_70","unstructured":"CLSI Clinical and Laboratory Standards Institute (CLSI) (2020). Performance Standards for Antimicrobial Susceptibility Testing, CLSI. [30th ed.]. CLSI Supplement M100."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/23\/5743\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:47:28Z","timestamp":1760114848000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/23\/5743"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,12,5]]},"references-count":70,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["molecules29235743"],"URL":"https:\/\/doi.org\/10.3390\/molecules29235743","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,12,5]]}}}