[en] Combining the redox activity and remarkable adhesion propensity of polyphenols (such as catechol or pyrogallol) with the numerous tunable properties of poly(ionic liquid)s (PILs) is an attractive route to design inventive multifunctional macro-molecular platforms. In this contribution, we describe the first synthesis of a novel family of structurally well-defined PILs functionalized with catechol/pyrogallol/phenol pendants by organometallic-mediated radical polymerization (OMRP) using an alkyl−cobalt(III) complex as initiator and mediating agent. The living character of the chains is also exploited to produce di-and triblock PILs, and the facile counteranion exchange reactions afforded a library of PILs-bearing free phenol/catechol/pyrogallol moieties. Electrochemical investigations of catechol/pyrogallol-derived PILs in aqueous medium demonstrated the characteristic catechol to o-quinone transformations, whereas, quasi-reversible doping/undoping with supporting electrolyte cations (Li + /tetrabutylammonium +) has been observed in organic media, suggesting a bright future for this new family of redox-active PILs as cathode material for secondary energy storage devices. Also, pendant catechol/pyrogallol groups mediated sustained anchoring onto the gold surface conferred PILs properties to the interface. As a proof-of-concept, both the adsorption and inhibition of proteins on polymer modified surfaces have been demonstrated in real time using the quartz crystal microbalance with dissipation technique. The exquisite physicochemical tunability of these innovative surface-and redox-active PILs makes them excellent candidates for a broad range of potential applications, including " smart surfaces " and electrochemical energy storage devices.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM) CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Patil, Nagaraj ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Cordella, Daniela; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Aqil, Abdelhafid ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Debuigne, Antoine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Admassie, Shimelis; Linköping University, Biomolecular and organic electronics, Sweden > Addis Ababa University, Department of Chemistry, Ethiopia
Jérôme, Christine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Surface- and redox-active multifunctional polyphenol-derived poly(ionic liquid)s: controlled synthesis and characterization
Publication date :
25 October 2016
Journal title :
Macromolecules
ISSN :
0024-9297
eISSN :
1520-5835
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
49
Issue :
20
Pages :
7676-7691
Peer reviewed :
Peer Reviewed verified by ORBi
European Projects :
FP7 - 289347 - RENAISSANCE - TRAINING NETWORK IN INNOVATIVE POLYELECTROLYTES FOR ENERGY AND ENVIRONMENT
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique CE - Commission Européenne
Lu, J.; Yan, F.; Texter, J. Advanced Applications of Ionic Liquids in Polymer Science Prog. Polym. Sci. 2009, 34 (5) 431-448 10.1016/j.progpolymsci.2008.12.001
Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati, B. Ionic-Liquid Materials for the Electrochemical Challenges of the Future Nat. Mater. 2009, 8 (8) 621-629 10.1038/nmat2448
Kubisa, P. Ionic Liquids as Solvents for Polymerization processes-Progress and Challenges Prog. Polym. Sci. 2009, 34 (12) 1333-1347 10.1016/j.progpolymsci.2009.09.001
Green, O.; Grubjesic, S.; Lee, S.; Firestone, M. A. The Design of Polymeric Ionic Liquids for the Preparation of Functional Materials Polym. Rev. 2009, 49 (4) 339-360 10.1080/15583720903291116
Anderson, E. B.; Long, T. E. Imidazole- and Imidazolium-Containing Polymers for Biology and Material Science Applications Polymer 2010, 51 (12) 2447-2454 10.1016/j.polymer.2010.02.006
Mecerreyes, D. Polymeric Ionic Liquids: Broadening the Properties and Applications of Polyelectrolytes Prog. Polym. Sci. 2011, 36 (12) 1629-1648 10.1016/j.progpolymsci.2011.05.007
Yuan, J.; Mecerreyes, D.; Antonietti, M. Poly(ionic Liquid)s: An Update Prog. Polym. Sci. 2013, 38 (7) 1009-1036 10.1016/j.progpolymsci.2013.04.002
MacFarlane, D. R.; Tachikawa, N.; Forsyth, M.; Pringle, J. M.; Howlett, P. C.; Elliott, G. D.; Davis, J. H.; Watanabe, M.; Simon, P.; Angell, C. A. Energy Applications of Ionic Liquids Energy Environ. Sci. 2014, 7 (1) 232-250 10.1039/C3EE42099J
Kuzmicz, D.; Coupillaud, P.; Men, Y.; Vignolle, J.; Vendraminetto, G.; Ambrogi, M.; Taton, D.; Yuan, J. Functional Mesoporous Poly(ionic Liquid)-Based Copolymer Monoliths: From Synthesis to Catalysis and Microporous Carbon Production Polymer 2014, 55 (16) 3423-3430 10.1016/j.polymer.2014.04.032
Täuber, K.; Zhao, Q.; Antonietti, M.; Yuan, J. Tuning the Pore Size in Gradient Poly(ionic Liquid) Membranes by Small Organic Acids ACS Macro Lett. 2015, 4 (1) 39-42 10.1021/mz500674d
Shaplov, A. S.; Marcilla, R.; Mecerreyes, D. Recent Advances in Innovative Polymer Electrolytes Based on Poly(ionic Liquid)s Electrochim. Acta 2015, 175, 18-34 10.1016/j.electacta.2015.03.038
Ho, T. D.; Zhang, C.; Hantao, L. W.; Anderson, J. L. Ionic Liquids in Analytical Chemistry: Fundamentals, Advances, and Perspectives Anal. Chem. 2014, 86 (1) 262-285 10.1021/ac4035554
Suzuki, Y.; Nishide, H.; Tsuchida, E. Membranes of the Picket Fence Cobalt Porphyrin Complexed with Poly(vinylimidazole and -Pyridine)s: Selective Optical Response to Oxygen Macromolecules 2000, 33 (7) 2530-2534 10.1021/ma9917949
Suzuki, M.; Kimura, M.; Shirai, H. Photo- and Thermo-Chromism of a ruthenium(II) Complex and Viologen-Containing Polymer Film Chem. Commun. 1997, 2061-2062 10.1039/a705107g
Coman, V.; Gustavsson, T.; Finkelsteinas, A.; von Wachenfeldt, C.; Hägerhäll, C.; Gorton, L. Electrical Wiring of Live, Metabolically Enhanced Bacillus Subtilis Cells with Flexible Osmium-Redox Polymers J. Am. Chem. Soc. 2009, 131 (44) 16171-16176 10.1021/ja905442a
Feng, X.; Sui, X.; Hempenius, M. A.; Vancso, G. J. Electrografting of Stimuli-Responsive, Redox Active Organometallic Polymers to Gold from Ionic Liquids J. Am. Chem. Soc. 2014, 136 (22) 7865-7868 10.1021/ja503807r
Gracia, R.; Vijayakrishna, K.; Mecerreyes, D. Poly(ionic Liquid)s with Redox Active Counter-Anions: All-in-One Reactants and Stabilizers for the Synthesis of Functional Colloids React. Funct. Polym. 2014, 79 (1) 54-58 10.1016/j.reactfunctpolym.2014.03.005
Bui-Thi-Tuyet, V.; Trippé-Allard, G.; Ghilane, J.; Randriamahazaka, H. Surface and Electrochemical Properties of Polymer Brush-Based Redox Poly(Ionic Liquid) ACS Appl. Mater. Interfaces 2016, 10.1021/acsami.6b02107
Suga, T.; Sakata, M.; Aoki, K.; Nishide, H. Synthesis of Pendant Radical- and Ion-Containing Block Copolymers via Ring-Opening Metathesis Polymerization for Organic Resistive Memory ACS Macro Lett. 2014, 3 (8) 703-707 10.1021/mz500273z
Yang, J.; Cohen Stuart, M. A.; Kamperman, M. Jack of All Trades: Versatile Catechol Crosslinking Mechanisms Chem. Soc. Rev. 2014, 43 (24) 8271-8298 10.1039/C4CS00185K
Ye, Q.; Zhou, F.; Liu, W. Bioinspired Catecholic Chemistry for Surface Modification Chem. Soc. Rev. 2011, 40 (7) 4244 10.1039/c1cs15026j
Faure, E.; Falentin-Daudré, C.; Jérôme, C.; Lyskawa, J.; Fournier, D.; Woisel, P.; Detrembleur, C. Catechols as Versatile Platforms in Polymer Chemistry Prog. Polym. Sci. 2013, 38 (1) 236-270 10.1016/j.progpolymsci.2012.06.004
Moulay, S. Dopa/Catechol-Tethered Polymers: Bioadhesives and Biomimetic Adhesive Materials Polym. Rev. 2014, 54 (3) 436-513 10.1080/15583724.2014.881373
White, J. D.; Wilker, J. J. Underwater Bonding with Charged Polymer Mimics of Marine Mussel Adhesive Proteins Macromolecules 2011, 44 (13) 5085-5088 10.1021/ma201044x
Isakova, A.; Topham, P. D.; Sutherland, A. J. Controlled RAFT Polymerization and Zinc Binding Performance of Catechol-Inspired Homopolymers Macromolecules 2014, 47 (8) 2561-2568 10.1021/ma500336u
Lee, H.; Lee, B. P.; Messersmith, P. B. A Reversible Wet/dry Adhesive Inspired by Mussels and Geckos Nature 2007, 448 (7151) 338-341 10.1038/nature05968
Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-Inspired Surface Chemistry for Multifunctional Coatings Science (Washington, DC, U. S.) 2007, 318 (5849) 426-430 10.1126/science.1147241
Lee, B. P.; Messersmith, P. B.; Israelachvili, J. N.; Waite, J. H. Mussel-Inspired Adhesives and Coatings Annu. Rev. Mater. Res. 2011, 41 (1) 99-132 10.1146/annurev-matsci-062910-100429
Lee, H.; Rho, J.; Messersmith, P. B. Facile Conjugation of Biomolecules onto Surfaces via Mussel Adhesive Protein Inspired Coatings Adv. Mater. 2009, 21 (4) 431-434 10.1002/adma.200801222
Faure, E.; Lecomte, P.; Lenoir, S.; Vreuls, C.; Van De Weerdt, C.; Archambeau, C.; Martial, J.; Jérôme, C.; Duwez, A.-S.; Detrembleur, C. Sustainable and Bio-Inspired Chemistry for Robust Antibacterial Activity of Stainless Steel J. Mater. Chem. 2011, 21 (22) 7901 10.1039/c1jm11380a
Faure, E.; Falentin-Daudré, C.; Lanero, T. S.; Vreuls, C.; Zocchi, G.; Van De Weerdt, C.; Martial, J.; Jérôme, C.; Duwez, A.-S.; Detrembleur, C. Functional Nanogels as Platforms for Imparting Antibacterial, Antibiofilm, and Antiadhesion Activities to Stainless Steel Adv. Funct. Mater. 2012, 22 (24) 5271-5282 10.1002/adfm.201201106
Yeroslavsky, G.; Girshevitz, O.; Foster-Frey, J.; Donovan, D. M.; Rahimipour, S. Antibacterial and Antibiofilm Surfaces through Polydopamine-Assisted Immobilization of Lysostaphin as an Antibacterial Enzyme Langmuir 2015, 31 (3) 1064-1073 10.1021/la503911m
Cheng, G.; Zheng, S.-Y. Construction of a High-Performance Magnetic Enzyme Nanosystem for Rapid Tryptic Digestion Sci. Rep. 2014, 4, 6947 10.1038/srep06947
He, H.; Luebke, D.; Nulwala, H.; Matyjaszewski, K. Synthesis of Poly(ionic Liquid)s by Atom Transfer Radical Polymerization with Ppm of Cu Catalyst Macromolecules 2014, 47 (19) 6601-6609 10.1021/ma501487u
Vijayakrishna, K.; Jewrajka, S. K.; Ruiz, A.; Marcilla, R.; Pomposo, J. A.; Mecerreyes, D.; Taton, D.; Gnanou, Y. Synthesis by RAFT and Ionic Responsiveness of Double Hydrophilic Block Copolymers Based on Ionic Liquid Monomer Units Macromolecules 2008, 41 (17) 6299-6308 10.1021/ma800677h
Chen, H.; Choi, J.-H.; Salas-de la Cruz, D.; Winey, K. I.; Elabd, Y. A. Polymerized Ionic Liquids: The Effect of Random Copolymer Composition on Ion Conduction Macromolecules 2009, 42 (13) 4809-4816 10.1021/ma900713e
Mori, H.; Yahagi, M.; Endo, T. RAFT Polymerization of N -Vinylimidazolium Salts and Synthesis of Thermoresponsive Ionic Liquid Block Copolymers Macromolecules 2009, 42 (21) 8082-8092 10.1021/ma901180j
Detrembleur, C.; Debuigne, A.; Hurtgen, M.; Jérôme, C.; Pinaud, J.; Fèvre, M.; Coupillaud, P.; Vignolle, J.; Taton, D. Synthesis of 1-Vinyl-3-Ethylimidazolium-Based Ionic Liquid (Co)polymers by Cobalt-Mediated Radical Polymerization Macromolecules 2011, 44 (16) 6397-6404 10.1021/ma201041s
Coupillaud, P.; Fèvre, M.; Wirotius, A.-L.; Aissou, K.; Fleury, G.; Debuigne, A.; Detrembleur, C.; Mecerreyes, D.; Vignolle, J.; Taton, D. Precision Synthesis of Poly(Ionic Liquid)-Based Block Copolymers by Cobalt-Mediated Radical Polymerization and Preliminary Study of Their Self-Assembling Properties Macromol. Rapid Commun. 2014, 35 (4) 422-430 10.1002/marc.201300776
Cordella, D.; Kermagoret, A.; Debuigne, A.; Riva, R.; German, I.; Isik, M.; Jérôme, C.; Mecerreyes, D.; Taton, D.; Detrembleur, C. Direct Route to Well-Defined Poly(ionic Liquid)s by Controlled Radical Polymerization in Water ACS Macro Lett. 2014, 3 (12) 1276-1280 10.1021/mz500721r
Cordella, D.; Kermagoret, A.; Debuigne, A.; Jérôme, C.; Mecerreyes, D.; Isik, M.; Taton, D.; Detrembleur, C. All Poly(ionic Liquid)-Based Block Copolymers by Sequential Controlled Radical Copolymerization of Vinylimidazolium Monomers Macromolecules 2015, 48 (15) 5230-5243 10.1021/acs.macromol.5b01013
Weiss-Maurin, M.; Cordella, D.; Jérôme, C.; Taton, D.; Detrembleur, C. Direct One-Pot Synthesis of Poly(ionic Liquid) Nanogels by Cobalt-Mediated Radical Cross-Linking Copolymerization in Organic or Aqueous Media Polym. Chem. 2016, 7 (14) 2521-2530 10.1039/C6PY00112B
Cordella, D.; Debuigne, A.; Jérôme, C.; Kochovski, Z.; Taton, D.; Detrembleur, C. One-Pot Synthesis of Double Poly(Ionic Liquid) Block Copolymers by Cobalt-Mediated Radical Polymerization-Induced Self-Assembly (CMR-PISA) in Water Macromol. Rapid Commun. 2016, 37, 1181 10.1002/marc.201600039
Debuigne, A.; Champouret, Y.; Jérôme, R.; Poli, R.; Detrembleur, C. Mechanistic Insights into the Cobalt-Mediated Radical Polymerization (CMRP) of Vinyl Acetate with cobalt(III) Adducts as Initiators Chem.-Eur. J. 2008, 14 (13) 4046-4059 10.1002/chem.200701867
He, H.; Zhong, M.; Adzima, B.; Luebke, D.; Nulwala, H.; Matyjaszewski, K. A Simple and Universal Gel Permeation Chromatography Technique for Precise Molecular Weight Characterization of Well-Defined Poly(ionic Liquid)s J. Am. Chem. Soc. 2013, 135 (11) 4227-4230 10.1021/ja4012645
Weissman, S. A.; Zewge, D. Recent Advances in Ether Dealkylation Tetrahedron 2005, 61 (33) 7833-7863 10.1016/j.tet.2005.05.041
Percec, V.; Sun, H. J.; Leowanawat, P.; Peterca, M.; Graf, R.; Spiess, H. W.; Zeng, X.; Ungar, G.; Heiney, P. A. Transformation from Kinetically into Thermodynamically Controlled Self-Organization of Complex Helical Columns with 3d Periodicity Assembled from Dendronized Perylene Bisimides J. Am. Chem. Soc. 2013, 135 (10) 4129-4148 10.1021/ja400639q
Percec, V.; Peterca, M.; Sienkowska, M. J.; Ilies, M. A.; Aqad, E.; Smidrkal, J.; Heiney, P. A. Synthesis and Retrostructural Analysis of Libraries of AB3 and Constitutional Isomeric AB2 Phenylpropyl Ether-Based Supramolecular Dendrimers J. Am. Chem. Soc. 2006, 128 (10) 3324-3334 10.1021/ja060062a
Percec, V.; Imam, M. R.; Peterca, M.; Wilson, D. A.; Heiney, P. A. Self-Assembly of Dendritic Crowns into Chiral Supramolecular Spheres J. Am. Chem. Soc. 2009, 131 (3) 1294-1304 10.1021/ja8087778
Yuan, J.; Antonietti, M. Poly(ionic Liquid) Latexes Prepared by Dispersion Polymerization of Ionic Liquid Monomers Macromolecules 2011, 44 (4) 744-750 10.1021/ma102858b
Paulini, R.; Lerner, C.; Diederich, F.; Jakob-Roetne, R.; Zürcher, G.; Borroni, E. Synthesis and Biological Evaluation of Potent Bisubstrate Inhibitors of the Enzyme Catechol O-Methyltransferase (COMT) Lacking a Nitro Group Helv. Chim. Acta 2006, 89 (9) 1856-1887 10.1002/hlca.200690179
Grice, C. A.; Tays, K. L.; Savall, B. M.; Wei, J.; Butler, C. R.; Axe, F. U.; Bembenek, S. D.; Fourie, A. M.; Dunford, P. J.; Lundeen, K.; Coles, F.; Xue, X.; Riley, J. P.; Williams, K. N.; Karlsson, L.; Edwards, J. P. Identification of a Potent, Selective, and Orally Active Leukotriene A4 Hydrolase Inhibitor with Anti-Inflammatory Activity J. Med. Chem. 2008, 51 (14) 4150-4169 10.1021/jm701575k
Bunck, D. N.; Sorenson, G. P.; Mahanthappa, M. K. Cobalt-Mediated Radical Polymerization Routes to Poly(vinyl Ester) Block Copolymers J. Polym. Sci., Part A: Polym. Chem. 2011, 49 (1) 242-249 10.1002/pola.24445
Kermagoret, A.; Debuigne, A.; Jérôme, C.; Detrembleur, C. Precision Design of Ethylene- and Polar-Monomer-Based Copolymers by Organometallic-Mediated Radical Polymerization Nat. Chem. 2014, 6 (3) 179-187 10.1038/nchem.1850
Arteaga, J. F.; Ruiz-Montoya, M.; Palma, A.; Alonso-Garrido, G.; Pintado, S.; Rodríguez-Mellado, J. M. Comparison of the Simple Cyclic Voltammetry (CV) and DPPH Assays for the Determination of Antioxidant Capacity of Active Principles Molecules 2012, 17 (12) 5126-5138 10.3390/molecules17055126
Chevion, S.; Roberts, M. A.; Chevion, M. The Use of Cyclic Voltammetry for the Evaluation of Antioxidant Capacity Free Radical Biol. Med. 2000, 28 (6) 860-870 10.1016/S0891-5849(00)00178-7
Crozier, A.; Jaganath, I. B.; Clifford, M. N. Dietary Phenolics: Chemistry, Bioavailability and Effects on Health Nat. Prod. Rep. 2009, 26 (8) 1001-1043 10.1039/b802662a
Kocaçalişkan, I.; Talan, I.; Terzi, I. Antimicrobial Activity of Catechol and Pyrogallol as Allelochemicals Z. Naturforsch., C: J. Biosci. 2006, 61 (9-10) 639-642 10.1515/znc-2006-9-1004
Taguri, T.; Tanaka, T.; Kouno, I. Antimicrobial Activity of 10 Different Plant Polyphenols against Bacteria Causing Food-Borne Disease Biol. Pharm. Bull. 2004, 27 (12) 1965-1969 10.1248/bpb.27.1965
Liu, L.; Huang, Y.; Riduan, S. N.; Gao, S.; Yang, Y.; Fan, W.; Zhang, Y. Main-Chain Imidazolium Oligomer Material as a Selective Biomimetic Antimicrobial Agent Biomaterials 2012, 33 (33) 8625-8631 10.1016/j.biomaterials.2012.08.006
Schrekker, H. S.; Donato, R. K.; Fuentefria, A. M.; Bergamo, V.; Oliveira, L. F.; Machado, M. M. Imidazolium Salts as Antifungal Agents: Activity against Emerging Yeast Pathogens, without Human Leukocyte Toxicity MedChemComm 2013, 4 (11) 1457 10.1039/c3md00222e
Chin, W.; Yang, C.; Ng, V. W. L.; Huang, Y.; Cheng, J.; Tong, Y. W.; Coady, D. J.; Fan, W.; Hedrick, J. L.; Yang, Y. Y. Biodegradable Broad-Spectrum Antimicrobial Polycarbonates: Investigating the Role of Chemical Structure on Activity and Selectivity Macromolecules 2013, 46 (22) 8797-8807 10.1021/ma4019685
Zheng, Z.; Xu, Q.; Guo, J.; Qin, J.; Mao, H.; Wang, B.; Yan, F. Structure-Antibacterial Activity Relationships of Imidazolium-Type Ionic Liquid Monomers, Poly(ionic Liquids) and Poly(ionic Liquid) Membranes: Effect of Alkyl Chain Length and Cations ACS Appl. Mater. Interfaces 2016, 8 (20) 12684-12692 10.1021/acsami.6b03391
Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis; Wuts, P. G. M., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2014.
MacFarlane, D. R.; Forsyth, M.; Howlett, P. C.; Pringle, J. M.; Sun, J.; Annat, G.; Neil, W.; Izgorodina, E. I. Ionic Liquids in Electrochemical Devices and Processes: Managing Interfacial Electrochemistry Acc. Chem. Res. 2007, 40 (11) 1165-1173 10.1021/ar7000952
Matos-Pérez, C. R.; White, J. D.; Wilker, J. J. Polymer Composition and Substrate Influences on the Adhesive Bonding of a Biomimetic, Cross-Linking Polymer J. Am. Chem. Soc. 2012, 134 (22) 9498-9505 10.1021/ja303369p
Marcilla, R.; Blazquez, J. A.; Rodriguez, J.; Pomposo, J. A.; Mecerreyes, D. Tuning the Solubility of Polymerized Ionic Liquids by Simple Anion-Exchange Reactions J. Polym. Sci., Part A: Polym. Chem. 2004, 42 (1) 208-212 10.1002/pola.11015
Marcilla, R.; Blazquez, J. A.; Fernandez, R.; Grande, H.; Pomposo, J. A.; Mecerreyes, D. Synthesis of Novel Polycations Using the Chemistry of Ionic Liquids Macromol. Chem. Phys. 2005, 206 (2) 299-304 10.1002/macp.200400411
Awad, W. H.; Gilman, J. W.; Nyden, M.; Harris, R. H.; Sutto, T. E.; Callahan, J.; Trulove, P. C.; DeLong, H. C.; Fox, D. M. Thermal Degradation Studies of Alkyl-Imidazolium Salts and Their Application in Nanocomposites Thermochim. Acta 2004, 409 (1) 3-11 10.1016/S0040-6031(03)00334-4
Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. Thermophysical Properties of Imidazolium-Based Ionic Liquids J. Chem. Eng. Data 2004, 49 (4) 954-964 10.1021/je034261a
Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. The Possible Role of Proton-Coupled Electron Transfer (PCET) in Water Oxidation by Photosystem II Angew. Chem., Int. Ed. 2007, 46 (28) 5284-5304 10.1002/anie.200600917
Marcus, R. A.; Sutin, N. Electron Transfers in Chemistry and Biology Biochim. Biophys. Acta, Rev. Bioenerg. 1985, 811 (3) 265-322 10.1016/0304-4173(85)90014-X
Häupler, B.; Wild, A.; Schubert, U. S. Carbonyls: Powerful Organic Materials for Secondary Batteries Adv. Energy Mater. 2015, 5 (11) 1402034 10.1002/aenm.201402034
Liu, Y.; Ai, K.; Lu, L. Polydopamine and Its Derivative Materials: Synthesis and Promising Applications in Energy, Environmental, and Biomedical Fields Chem. Rev. 2014, 114 (9) 5057-5115 10.1021/cr400407a
Dandawate, P. R.; Vyas, A. C.; Padhye, S. B.; Singh, M. W.; Baruah, J. B. Perspectives on Medicinal Properties of Benzoquinone Compounds Mini-Rev. Med. Chem. 2010, 10 (5) 436-454 10.2174/138955710791330909
Lin, Q.; Li, Q.; Batchelor-Mcauley, C.; Compton, R. G. Two-Electron, Two-Proton Oxidation of Catechol: Kinetics and Apparent Catalysis J. Phys. Chem. C 2015, 119 (3) 1489-1495 10.1021/jp511414b
Costentin, C.; Robert, M.; Savéant, J.-M. Concerted Proton-Electron Transfers in the Oxidation of Phenols Phys. Chem. Chem. Phys. 2010, 12 (37) 11179-11190 10.1039/c0cp00063a
Eggins, B. R.; Chambers, J. Q. Electrochemical Oxidation of Hydroquinone in Acetonitrile J. Chem. Soc. D 1969, 58 (5) 232 10.1039/c29690000232
Ji, X.; Banks, C. E.; Silvester, D. S.; Wain, A. J.; Compton, R. G. Electrode Kinetic Studies of the Hydroquinone-Benzoquinone System and the Reaction between Hydroquinone and Ammonia in Propylene Carbonate: Application to the Indirect Electroanalytical Sensing of Ammonia J. Phys. Chem. C 2007, 111 (3) 1496-1504 10.1021/jp066704y
Guin, P. S.; Das, S.; Mandal, P. C. Electrochemical Reduction of Quinones in Different Media: A Review Int. J. Electrochem. 2011, 2011 (3) 1-22 10.4061/2011/816202
Yamamoto, T.; Kimura, T.; Shiraishi, K. Preparation of π-Conjugated Polymers Composed of Hydroquinone, P -Benzoquinone, and P -Diacetoxyphenylene Units. Optical and Redox Properties of the Polymers Macromolecules 1999, 32 (26) 8886-8896 10.1021/ma9907946
Wain, A. J.; Wildgoose, G. G.; Heald, C. G. R.; Jiang, L.; Jones, T. G. J.; Compton, R. G. Electrochemical ESR and Voltammetric Studies of Lithium Ion Pairing with Electrogenerated 9,10-Anthraquinone Radical Anions Either Free in Acetonitrile Solution or Covalently Bound to Multiwalled Carbon Nanotubes J. Phys. Chem. B 2005, 109 (9) 3971-3978 10.1021/jp040552u
Fujinaga, T.; Izutsu, K.; Nomura, T. Effect of Metal Ions on the Polarographic Reduction of Organic Compounds in Dipolar Arrotic Solvents J. Electroanal. Chem. Interfacial Electrochem. 1971, 29 (1) 203-209 10.1016/S0022-0728(71)80083-9
Choi, N.-S.; Chen, Z.; Freunberger, S. A.; Ji, X.; Sun, Y.-K.; Amine, K.; Yushin, G.; Nazar, L. F.; Cho, J.; Bruce, P. G. Challenges Facing Lithium Batteries and Electrical Double-Layer Capacitors Angew. Chem., Int. Ed. 2012, 51 (40) 9994-10024 10.1002/anie.201201429
Kim, T. Y.; Lee, H. W.; Stoller, M.; Dreyer, D. R.; Bielawski, C. W.; Ruoff, R. S.; Suh, K. S. High-Performance Supercapacitors Based on Poly(ionic Liquid)-Modified Graphene Electrodes ACS Nano 2011, 5 (1) 436-442 10.1021/nn101968p
Marcilla, R.; Curri, M. L.; Cozzoli, P. D.; Martínez, M. T.; Loinaz, I.; Grande, H.; Pomposo, J. A.; Mecerreyes, D. Nano-Objects on a Round Trip from Water to Organics in a Polymeric Ionic Liquid Vehicle Small 2006, 2 (4) 507-512 10.1002/smll.200500373
Kim, T.; Lee, H.; Kim, J.; Suh, K. S. Synthesis of Phase Transferable Graphene Sheets Using Ionic Liquid Polymers ACS Nano 2010, 4 (3) 1612-1618 10.1021/nn901525e
Benoit, C.; Demeter, D.; Bélanger, D.; Cougnon, C. A Redox-Active Binder for Electrochemical Capacitor Electrodes Angew. Chem., Int. Ed. 2016, 55 (17) 5318-5321 10.1002/anie.201601395
Donlan, R. M. Biofilm Formation: A Clinically Relevant Microbiological Process Clin. Infect. Dis. 2001, 33 (8) 1387-1392 10.1086/322972
Harding, J. L.; Reynolds, M. M. Combating Medical Device Fouling Trends Biotechnol. 2014, 32 (3) 140-146 10.1016/j.tibtech.2013.12.004
Banerjee, I.; Pangule, R. C.; Kane, R. S. Antifouling Coatings: Recent Developments in the Design of Surfaces That Prevent Fouling by Proteins, Bacteria, and Marine Organisms Adv. Mater. 2011, 23 (6) 690-718 10.1002/adma.201001215
Vladkova, T. G. Surface Engineered Polymeric Biomaterials with Improved Biocontact Properties Int. J. Polym. Sci. 2010, 2010, 296094 10.1155/2010/296094
Yang, J.; Hua, Z.; Wang, T.; Wu, B.; Liu, G.; Zhang, G. Counterion-Specific Protein Adsorption on Polyelectrolyte Brushes Langmuir 2015, 31 (22) 6078-6084 10.1021/acs.langmuir.5b01145
Shu, Y.; Liu, M.; Chen, S.; Chen, X.; Wang, J. New Insight into Molecular Interactions of Imidazolium Ionic Liquids with Bovine Serum Albumin J. Phys. Chem. B 2011, 115 (42) 12306-12314 10.1021/jp2071925
Wang, X.; Ho, C.-T.; Huang, Q. Investigation of Adsorption Behavior of (-)-Epigallocatechin Gallate on Bovine Serum Albumin Surface Using Quartz Crystal Microbalance with Dissipation Monitoring J. Agric. Food Chem. 2007, 55 (13) 4987-4992 10.1021/jf070590l