{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:48:12Z","timestamp":1787028492708,"version":"build-2736575974"},"reference-count":34,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2022,12,8]],"date-time":"2022-12-08T00:00:00Z","timestamp":1670457600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Russian Science Foundation","award":["22-23-20196"],"award-info":[{"award-number":["22-23-20196"]}]},{"DOI":"10.13039\/501100006769","name":"Cabinet of Ministers of the Republic of Tatarstan","doi-asserted-by":"publisher","award":["22-23-20196"],"award-info":[{"award-number":["22-23-20196"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Herein, the synthesis of ferrocene-containing salts is presented. Acylation of ferrocene (Fc) according to the Friedel\u2013Crafts method led to \u03c9-bromoacyl ferrocenes. The \u03c9-bromoacyl ferrocenes were subsequently introduced to quaternization reaction with tri-tert-butyl phosphine, which resulted in phosphonium salts. Obtained phosphonium salts were characterized by physical methods. The electrochemical properties of phosphonium salts were studied by cyclic voltammetry (CV). It was found that the replacement of n-butyl fragments at the phosphorus atom by tert-butyl leads to a more anodic potential shift. In contrast to isolobal structures Fc-C(O)(CH2)nP+(n-Bu)3X\u2212 and Fc-(CH2)n+1P+(n-Bu)3X\u2212, the CV curves of Fc-C(O)(CH2)nP+(t-Bu)3X\u2212 and Fc-(CH2)n+1P+(t-Bu)3X\u2212 did not show a large discrepancy between forward and reverse currents. The transformation of the C=O groups to CH2 fragments had a significant effect on the electrochemical properties of ferrocene salts, the oxidation potential of which is close to that of pure ferrocene.<\/jats:p>","DOI":"10.3390\/ijms232415534","type":"journal-article","created":{"date-parts":[[2022,12,8]],"date-time":"2022-12-08T03:35:53Z","timestamp":1670470553000},"page":"15534","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Conductive Mediators in Oxidation Based on Ferrocene Functionalized Phosphonium Ionic Liquids"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1606-4469","authenticated-orcid":false,"given":"Vadim V.","family":"Ermolaev","sequence":"first","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liliya R.","family":"Kadyrgulova","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4714-4143","authenticated-orcid":false,"given":"Mikhail N.","family":"Khrizanforov","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"},{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya Str. 18, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8473-5327","authenticated-orcid":false,"given":"Tatiana P.","family":"Gerasimova","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gulnaz R.","family":"Baembitova","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"},{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya Str. 18, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4661-6308","authenticated-orcid":false,"given":"Anna A.","family":"Lazareva","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"},{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya Str. 18, 420008 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8069-457X","authenticated-orcid":false,"given":"Vasili A.","family":"Miluykov","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov Street, 420088 Kazan, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"213846","DOI":"10.1016\/j.ccr.2021.213846","article-title":"Surface functionalization\u2013The way for advanced applications of smart materials","volume":"436","author":"Wieszczycka","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1002\/cplu.201900365","article-title":"Recent Advances on Stimuli-Responsive Smart Materials and their Applications","volume":"84","author":"Mrinalini","year":"2019","journal-title":"ChemPlusChem"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1007\/s12551-018-0419-2","article-title":"Ionic liquids: A brief history","volume":"10","author":"Welton","year":"2018","journal-title":"Biophys. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7132","DOI":"10.1021\/acs.chemrev.6b00562","article-title":"Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine","volume":"117","author":"Egorova","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2005522","DOI":"10.1002\/adfm.202005522","article-title":"Ionic Liquid-Based Stimuli-Responsive Functional Materials","volume":"30","author":"Cui","year":"2020","journal-title":"Adv. Funct. Mater."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1775","DOI":"10.1007\/s13738-020-01901-6","article-title":"Applications of phosphonium-based ionic liquids in chemical processes","volume":"17","author":"Khazalpour","year":"2020","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Zhang, H., Liu, L., Hou, P., Pan, H., and Fu, S. (2022). Polyisocyanide Quaternary Ammonium Salts with Exceptionally Star-Shaped Structure for Enhanced Antibacterial Properties. Polymers, 14.","DOI":"10.3390\/polym14091737"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Metelytsia, L.O., Hodyna, D.M., Semenyuta, I.V., Kovalishyn, V.V., Rogalsky, S.P., Derevianko, K.Y., and Tetko, I.V. (2022). Theoretical and Experimental Studies of Phosphonium Ionic Liquids as Potential Antibacterials of MDR Acinetobacter baumannii. Antibiotics, 11.","DOI":"10.3390\/antibiotics11040491"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/j.coelec.2019.04.028","article-title":"Enabling new electrochemical methods with redox-active ionic liquids","volume":"15","author":"Rochefort","year":"2019","journal-title":"Cur. Opin. Electrochem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"e4701","DOI":"10.1002\/aoc.4701","article-title":"Synthesis and application of novel 1,2,3-triazolylferrocene-containing ionic liquid supported on Fe3O4 nanocatalyst in the synthesis of new pyran-substituted Betti bases: Novel nanocatalyst for the synthesis of pyran substituted Betti bases","volume":"33","author":"Esmati","year":"2019","journal-title":"Appl. Organomet. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"118933","DOI":"10.1016\/j.molliq.2022.118933","article-title":"Ferrocene based ionic liquid: Synthesis, structure, transport properties and mechanism of thermal degradation","volume":"355","author":"Arkhipova","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"20252","DOI":"10.1021\/acsomega.9b02559","article-title":"Label-Free Electrochemical Immunosensor Based on \u03b2-Cyclodextrin-Functionalized Helical Carbon Nanotube and Ionic Liquid Containing Ferrocene and Aldehyde Groups","volume":"4","author":"Shen","year":"2019","journal-title":"ACS Omega"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1002\/ejic.201600983","article-title":"Why is Ferrocene so Exceptional?","volume":"1","author":"Astruc","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_14","unstructured":"Elisabeth, S.P. (2011). Ferrocenes: Compounds, Properties and Applications, Nova Science Publishers."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1839","DOI":"10.1016\/0039-9140(95)01638-4","article-title":"Catalytic oxidation of ascorbic acid by some ferrocene derivative mediators at the glassy carbon electrode. Application to the voltammetric resolution of ascorbic acid and dopamine in the same sample","volume":"42","author":"Ojani","year":"1995","journal-title":"Talanta"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1039\/C6CC09412K","article-title":"Electrochromism of a bipolar reversible redox-active ferrocene\u2013viologen linked ionic liquid","volume":"53","author":"Tahara","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/acsami.8b16410","article-title":"Electrochromism of Ferrocene- and Viologen-Based Redox-Active Ionic Liquids Composite","volume":"11","author":"Tahara","year":"2019","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1007\/s11426-018-9348-5","article-title":"Redox-responsive ferrocene-containing poly(ionic liquid)s for antibacterial applications","volume":"62","author":"Zhang","year":"2018","journal-title":"Sci. China Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1515\/hc-2017-0140","article-title":"Efficient synthesis of new pyrano [3,2-b] pyran derivatives via Fe3O4@SiO2-IL-Fc catalyzed three-component reaction","volume":"23","author":"Esmati","year":"2017","journal-title":"Heterocycl. Commun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1016\/j.molliq.2018.11.042","article-title":"Novel ferrocene substituted benzimidazolium based ionic liquid immobilized on magnetite as an efficient nano-catalyst for the synthesis of pyran derivatives","volume":"275","author":"Mohammadi","year":"2019","journal-title":"Mol. Liq."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4123","DOI":"10.1002\/ejoc.201400061","article-title":"Synthesis and Characterization of New Ferrocene-Containing Ionic Liquids","volume":"19","author":"Gharib","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"19379","DOI":"10.1021\/jp206927w","article-title":"Electrochemistry of Ferrocene-Functionalized Phosphonium Ionic Liquids","volume":"115","author":"Weaver","year":"2011","journal-title":"J. Phys. Chem. C"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3750","DOI":"10.1039\/c3dt53402b","article-title":"Ferrocenyl-phosphonium ionic liquids\u2014Synthesis, characterisation and electrochemistry","volume":"43","author":"Sundermeyer","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Arkhipova, D.M., Ermolaev, V.V., Miluykov, V.A., Valeeva, F.G., Gaynanova, G.A., Zakharova, L.Y., Minyaev, M.E., and Ananikov, V.P. (2021). Tri-tert-butyl(n-alkyl)phosphonium Ionic Liquids: Structure, Properties and Application as Hybrid Catalyst Nanomaterials. Sustainability, 13.","DOI":"10.3390\/su13179862"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Ermolaev, V.V., Arkhipova, D.M., Miluykov, V.A., Lyubina, A.P., Amerhanova, S.K., Kulik, N.V., Voloshina, A.D., and Ananikov, V.P. (2022). Sterically Hindered Quaternary Phosphonium Salts (QPSs): Antimicrobial Activity and Hemolytic and Cytotoxic Properties. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23010086"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"804","DOI":"10.1007\/s11172-022-3481-7","article-title":"Micellar nanocontainers based on sterically hindered cationic phosphonium amphiphiles","volume":"71","author":"Arkhipova","year":"2022","journal-title":"Rus. Chem. Bull."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2883","DOI":"10.1007\/s10008-015-2901-0","article-title":"Novel paste electrodes based on phosphonium salt room temperature ionic liquids for studying the redox properties of insoluble compounds","volume":"19","author":"Khrizanforov","year":"2015","journal-title":"J. Solid State Electrochem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1611","DOI":"10.1080\/10426507.2016.1217215","article-title":"Novel phosphonium salt for paste electrode to study the redox properties of insoluble compounds","volume":"191","author":"Khrizanforov","year":"2016","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Ermolaev, V., Gerasimova, T., Kadyrgulova, L., Shekurov, R., Dolengovski, E., Kononov, A., Miluykov, V., Sinyashin, O., Katsyuba, S., and Budnikova, Y. (2018). Ferrocene-Containing Sterically Hindered Phosphonium Salts. Molecules, 23.","DOI":"10.3390\/molecules23112773"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"989","DOI":"10.1080\/10426507.2019.1630406","article-title":"Novel sterically hindered ferrocenyl-phosphonium salt","volume":"194","author":"Kadyrgulova","year":"2019","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Arkhipova, D.M., Ermolaev, V.V., Miluykov, V.A., Gubaidullin, A.T., Islamov, D.R., Kataeva, O.N., and Ananikov, V.P. (2020). Sterically Hindered Phosphonium Salts: Structure, Properties and Palladium Nanoparticle Stabilization. Nanomaterials, 10.","DOI":"10.3390\/nano10122457"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5304","DOI":"10.1016\/j.electacta.2006.02.001","article-title":"Diffusion coefficient of ferrocene in 1-butyl-3-methylimidazolium tetrafluoroborate\u2014Concentration dependence and solvent purity","volume":"51","author":"Eisele","year":"2006","journal-title":"Electrochim. Acta"},{"key":"ref_33","unstructured":"Zanello, P., Nervi, C., and De Biani, F.F. (2019). Inorganic electrochemistry: Theory, practice and application. R. Soc. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"17132","DOI":"10.1039\/C8CP01893F","article-title":"From ascorbic acid to furan derivatives: The gas phase acid catalyzed degradation of vitamin C","volume":"20","author":"Cimino","year":"2018","journal-title":"Phys. Chem. Chem. Phys."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/24\/15534\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:36:16Z","timestamp":1760146576000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/24\/15534"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,8]]},"references-count":34,"journal-issue":{"issue":"24","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["ijms232415534"],"URL":"https:\/\/doi.org\/10.3390\/ijms232415534","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,8]]}}}