Surface and Electrochemical Properties of Polymer Brush-Based Redox Poly(Ionic Liquid)

ACS Applied Materials and Interfaces

Volumn 8, Issue 42, 2016, Pages 28316-28324

  Bui Thi Tuyet, Van ^a   Trippé Allard, Gaëlle ^a   Ghilane, Jalal ^a   Randriamahazaka, Hyacinthe ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

electrochemistry; ionic liquid; polymerization; redox poly(ionic liquid); surface modifications

Indexed keywords

AMINO ACIDS; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYST ACTIVITY; CATALYTIC OXIDATION; ELECTROCHEMICAL SENSORS; ELECTROCHEMISTRY; ELECTRODES; ELECTROLYTES; FREE RADICAL REACTIONS; LIQUIDS; ORGANOMETALLICS; POLYMERIZATION; REDOX REACTIONS; SURFACE TREATMENT;

ELECTROCHEMICAL IMMOBILIZATION; ELECTROCHEMICAL INVESTIGATIONS; ELECTROCHEMICAL MEASUREMENTS; ELECTROCHEMICAL PERFORMANCE; NANO-STRUCTURED ELECTRODES; POLY(IONIC LIQUID)S; SOLVENT-FREE ELECTROLYTE; SURFACE INITIATED-ATOM TRANSFER RADICAL POLYMERIZATION;

IONIC LIQUIDS;

EID: 84993661731     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.6b02107     Document Type: Article

References (70)

1. Seddon, K. R. J. Ionic Liquids for Clean Technology J. Chem. Technol. Biotechnol. 1997, 68, 351-356 10.1002/(SICI)1097-4660(199704)68:4<351::AID-JCTB613>3.0.CO;2-4
2. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2084 10.1021/cr980032t
3. Park, M.; Zhang, X.; Chung, M.; Less, G. B.; Sastry, A. M. A Review of Conduction Phenomena in Li-Ion Batteries J. Power Sources 2010, 195, 7904-7929 10.1016/j.jpowsour.2010.06.060
4. de Souza, R. F.; Padilha, J. C.; Gonçalves, R. S.; Dupont, J. Room Temperature Dialkylimidazolium Ionic Liquid-Based Fuel Cells Electrochem. Commun. 2003, 5, 728-731 10.1016/S1388-2481(03)00173-5
5. Sun, J.; MacFarlane, D. R.; Forsyth, M. Novel Alkaline Polymer Electrolytes Based on Tetramethyl Ammonium Hydroxide Electrochim. Acta 2003, 48, 1971-1976 10.1016/S0013-4686(03)00174-9
6. Wang, P.; Zakeeruddin, S. M.; Exnar, I.; Grätzel, M. High Efficiency Dye-sensitized Nanocrystalline Solar Cells Based on Ionic Liquid Polymer Gel Electrolyte Chem. Commun. 2002, 2972-2973 10.1039/B209322G
7. 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, 339-360 10.1080/15583720903291116
8. Lu, J.; Yan, F.; Texter, J. Advanced Applications of Ionic Liquids in Polymer Science Prog. Polym. Sci. 2009, 34, 431-448 10.1016/j.progpolymsci.2008.12.001
9. Le Bideau, J.; Viau, L.; Vioux, A. Ionogels, Ionic Liquid Based Hybrid Materials Chem. Soc. Rev. 2011, 40, 907-925 10.1039/C0CS00059K
10. Yuan, J.; Antonietti, M. Poly(Ionic Liquid)s: Polymers Expanding Classical Property Profiles Polymer 2011, 52, 1469-1482 10.1016/j.polymer.2011.01.043
11. Mecerreyes, D. Polymeric Ionic Liquids: Broadening the Properties and Applications of Polyelectrolytes Prog. Polym. Sci. 2011, 36, 1629-1648 10.1016/j.progpolymsci.2011.05.007
12. Ueki, T.; Watanabe, M. Macromolecules in Ionic Liquids: Progress, Challenges, and Opportunities Macromolecules 2008, 41, 3739-3749 10.1021/ma800171k
13. Ohno, H. Design of Ion Conductive Polymers Based on Ionic Liquids Macromol. Symp. 2007, 249, 551-556 10.1002/masy.200750435
14. Yuan, J.; Mecerreyes, D.; Antonietti, M. Poly(Ionic Liquid)s: an Update Prog. Polym. Sci. 2013, 38, 1009-1036 10.1016/j.progpolymsci.2013.04.002
15. Ye, Y. S.; Rick, J.; Hwang, B. J. J. Ionic Liquid Polymer Electrolytes J. Mater. Chem. A 2013, 1, 2719-2743 10.1039/C2TA00126H
16. Opallo, M.; Lesniewski, A. A Review on Electrodes Modified with Ionic Liquids J. Electroanal. Chem. 2011, 656, 2-16 10.1016/j.jelechem.2011.01.008
17. Zhao, F.; Wu, X.; Wang, M.; Liu, Y.; Gao, L.; Dong, S. Electrochemical and Bioelectrochemistry Properties of Room-Temperature Ionic Liquids and Carbon Composite Materials Anal. Chem. 2004, 76, 4960-4967 10.1021/ac0494026
18. McCreery, R. L. Advanced Carbon Electrode Materials for Molecular Electrochemistry Chem. Rev. 2008, 108, 2646-2687 10.1021/cr068076m
19. Lu, J.; Yan, F.; Texter, J. Advanced Applications of Ionic Liquids in Polymer Science Prog. Polym. Sci. 2009, 34, 431-48 10.1016/j.progpolymsci.2008.12.001
20. Xiong, Y.; Wang, H.; Wang, R.; Yan, Y.; Zheng, B.; Wang, Y. A. A Facile One-step Synthesis to Cross-Linked Polymeric Nanoparticles as Highly Active and Selective Catalysts for Cycloaddition of CO2 to Epoxides Chem. Commun. 2010, 46, 3399-3401 10.1039/b926901k
21. Qiu, B.; Lin, B.; Si, Z.; Qiu, L.; Chu, F.; Zhao, J.; Yan, F. Bis-Imidazolium-Based Anion-Exchange Membranes for Alkaline Fuel Cells J. Power Sources 2012, 217, 329-335 10.1016/j.jpowsour.2012.06.041
22. Sui, X.; Hempenius, M. A.; Vancso, G. J. Redox-Active Cross-Linkable Poly(Ionic Liquid)s J. Am. Chem. Soc. 2012, 134, 4023-4025 10.1021/ja211662k
23. 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, 7865-7868 10.1021/ja503807r
24. Barbey, R.; Lavanant, L.; Paripovic, D.; Schüwer, N.; Sugnaux, C.; Tugulu, S.; Klok, H. A. Polymer Brushes via Surface-Initiated Controlled Radical Polymerization: Synthesis, Characterization, Properties, and Applications Chem. Rev. 2009, 109, 5437-5527 10.1021/cr900045a
25. Salamone, J. C.; Israel, S. C.; Taylor, P.; Snider, B. Poly(Vinylimidazolium) Salts of Varying Hydrophilic-Hydrophobic Character J. Polym. Sci., Polym. Symp. 1974, 45, 65-73 10.1002/polc.5070450106
26. Salamone, J. C.; Israel, S. C.; Taylor, P.; Snider, B. Synthesis and Homopolymerization of Vinylimidazolium Salts Polymer 1973, 14, 639-644 10.1016/0032-3861(73)90039-6
27. Yoshizawa, M.; Ohno, H. Molecular Brush Having Molten Salt Domain for Fast Ion Conduction Chem. Lett. 1999, 889-890 10.1246/cl.1999.889
28. Fellinger, T. P.; Thomas, A.; Yuan, J.; Antonietti, M. Cooking Carbon with Salt: Carbon Materials and Carbonaceous Frameworks from Ionic liquids and Poly(Ionic Liquid)s Adv. Mater. 2013, 25, 5838-5855 10.1002/adma.201301975
29. Yoshizawa, M.; Hirao, M.; Ito-Akita, K.; Ohno, H. Ion Conduction in Zwitterionic-Type Moltensalts and their Polymers J. Mater. Chem. 2001, 11, 1057-1062 10.1039/b101079o
30. Sato, T.; Morinaga, T.; Marukane, S.; Narutomi, T.; Igarashi, T.; Kawano, Y.; Ohno, K.; Fukuda, T.; Tsujii, Y. Novel Solid-State Polymer Electrolyte of Colloidal Crystal Decorated with Ionic-Liquid Polymer Brush Adv. Mater. 2011, 23, 4868-4872 10.1002/adma.201101983
31. Ling, Q. D.; Liaw, D. J.; Zhu, C.; Chan, D. H.; Kang, E. T.; Neoh, K. G. Polymer Electronic Memories: Materials, Devices and Mechanisms Prog. Polym. Sci. 2008, 33, 917-978 10.1016/j.progpolymsci.2008.08.001
32. George, P. M.; LaVan, D. A.; Burdick, J. A.; Chen, C. Y.; Liang, E.; Langer, E. Electrically Controlled Drug Delivery from Biotin-Doped Conductive Polypyrrole Adv. Mater. 2006, 18, 577-581 10.1002/adma.200501242
33. Yuan, L.; Wei, W.; Liu, S. Label-Free Electrochemical Immunosensors Based on Surface-Initiated Atom Radical Polymerization Biosens. Bioelectron. 2012, 38, 79-85 10.1016/j.bios.2012.05.007
34. Han, L. M.; Rajeshwar, K.; Timmons, R. B. Film Chemistry Control and Electrochemical Properties of Pulsed Plasma Polymerized Ferrocene and Vinylferrocene Langmuir 1997, 13, 5941-5950 10.1021/la9706779
35. Feng, X.; Zhang, K.; Hempenius, M. A.; Vancso, G. J. Organometallic Polymers for Electrode Decoration in Sensing Applications RSC Adv. 2015, 5, 106355-106376 10.1039/C5RA21256A
36. Glidle, A.; Hillman, A. R.; Ryder, K. S.; Smith, E. L.; Cooper, J.; Gadegaard, N.; Webster, J. R. P.; Dalgliesh, R.; Cubitt, R. Use of Neutron Reflectivity to Measure the Dynamics of Solvation and Structural Changes in Polyvinylferrocene Films During Electrochemically Controlled Redox Cycling Langmuir 2009, 25, 4093-4103 10.1021/la803234e
37. Kim, B. Y.; Ratcliff, E. L.; Armstrong, N. R.; Kowalewski, T.; Pyun, J. Ferrocene Functional Polymer Brushes on Indium Tin Oxide via Surface-Initiated Atom Transfer Radical Polymerization Langmuir 2010, 26, 2083-2092 10.1021/la902590u
38. Sakakiyama, T.; Ohkita, H.; Ohoka, M.; Ito, S.; Tsujii, Y.; Fukuda, T. Fabrication and Electrochemical Properties of High-density Graft Films with Ferrocene Moieties on ITO Substrates Chem. Lett. 2005, 34, 1366-1367 10.1246/cl.2005.1366
39. Lillethorup, M.; Torbensen, K.; Ceccato, M.; Pedersen, S. U.; Daasbjerg, K. Electron Transport Through a Diazonium-Based Initiator Layer to Covalently Attached Polymer Brushes of Ferrocenylmethyl Methacrylate Langmuir 2013, 29, 13595-13604 10.1021/la402535u
40. Xu, L. Q.; Wan, D.; Gong, H. F.; Neoh, K.-G.; Kang, E.-T.; Fu, G. D. One-Pot Preparation of Ferrocene-Functionalized Polymer Brushes on Gold Substrates by Combined Surface-Initiated Atom Transfer Radical Polymerization and "Click Chemistry Langmuir 2010, 26, 15376-15382 10.1021/la102775y
41. Park, S.; Kazlauskas, R. J. Improved Preparation and Use of Room-Temperature Ionic Liquids in Lipase-Catalyzed Enantio- and Regioselective Acylations J. Org. Chem. 2001, 66, 8395-8401 10.1021/jo015761e
42. Forgie, J. C.; El Khakani, S.; MacNeil, D. D.; Rochefort, D. Electrochemical Characterisation of a Lithium-Ion Battery Electrolyte Based on Mixtures of Carbonates with a Ferrocene-Functionalised Imidazolium Electroactive Ionic Liquid Phys. Chem. Chem. Phys. 2013, 15, 7713-7721 10.1039/c3cp50560j
43. Bélanger, D.; Pinson, J. Electrografting: a Powerful Method for Surface Modification Chem. Soc. Rev. 2011, 40, 3995-4048 10.1039/c0cs00149j
44. Matrab, T.; Chehimi, M. M.; Perruchot, C.; Adenier, A.; Guillez, A.; Save, M.; Charleux, B.; Cabet-Deliry, E.; Pinson, J. Novel Approach for Metallic Surface-Initiated Atom Transfer Radical Polymerization Using Electrografted Initiators Based on Aryl Diazonium Salts Langmuir 2005, 21, 4686-4694 10.1021/la046912m
45. Wang, M.; Schneider, A.; Jönsson, J. N.; Marcon, L.; Ghodbane, S.; Nethl, D. S.; Li, M.; Boukherroub, R.; Szunerits, S. Covalent Modification of Boron-Doped Diamond Electrodes with an Imidazolium-Based Ionic Liquid Electrochim. Acta 2010, 55, 1582-1587 10.1016/j.electacta.2009.10.029
46. Chi, Y. S.; Hwang, S.; Lee, B. S.; Kwak, J.; Choi, I. S.; Lee, S. Anion Exchange-Promoted Ru3+/2+ Redox Switch in Self-Assembled Monolayers of Imidazolium Ions on a Gold Electrode Langmuir 2005, 21, 4268-4271 10.1021/la046806k
47. Dedryvère, R.; Leroy, S.; Martinez, H.; Blanchard, F.; Lemordant, D.; Gonbeau, D. XPS Valence Characterization of Lithium Salts as a Tool to Study Electrode/Electrolyte Interfaces of Li-Ion Batteries J. Phys. Chem. B 2006, 110, 12986-12992 10.1021/jp061624f
48. Ghilane, J.; Lacroix, J. C. Formation of a Bifunctional Redox System Using Electrochemical Reduction of Platinum in Ferrocene Based Ionic Liquid and Its Reactivity with Aryldiazonium J. Am. Chem. Soc. 2013, 135, 4722-4728 10.1021/ja310889z
49. Iruthayaraj, J.; Chernyy, S.; Lillethorup, M.; Ceccato, M.; Røn, T.; Hinge, M.; Kingshott, P.; Besenbacher, F.; Pedersen, S. U.; Daasbjerg, K. On Surface-Initiated Atom Transfer Radical Polymerization Using Diazonium Chemistry To Introduce the Initiator Layer Langmuir 2011, 27, 1070-1078 10.1021/la104125n
50. Ishikawa, T.; Takenaka, A.; Kikuchi, M.; Kobayashi, M.; Takahara, A. Effective Addition of Organic Chloride Salts on Atom Transfer Radical Polymerization in Fluoroalcohols Macromolecules 2013, 46, 9189-9196 10.1021/ma401857w
51. Yu, B.; Zhou, F.; Hu, H.; Wang, C.; Liu, W. Synthesis and Properties of Polymer Brushes Bearing Ionic Liquid Moieties Electrochim. Acta 2007, 53, 487-494 10.1016/j.electacta.2007.07.018
52. Kim, B. Y.; Ratcliff, E. L.; Armstrong, N. R.; Kowalewski, T.; Pyun, J. Ferrocene Functional Polymer Brushes on Indium Tin Oxide via Surface-Initiated Atom Transfer Radical Polymerization Langmuir 2010, 26, 2083-2092 10.1021/la902590u
53. Rauch, S.; Uhlmann, P.; Eichhorn, E. J. In Situ Spectroscopic Ellipsometry of pH-Responsive Polymer Brushes on Gold Substrates Anal. Bioanal. Chem. 2013, 405, 9061-9069 10.1007/s00216-013-7090-z
54. Bard, A. J.; Faulkner, L. R. Electrochemical Methods. Fundamentals and Applications; Wiley: New York, 1980; p 522-545.
55. Laviron, E. General Expression of the Linear Potential Sweep Voltammogram in the Case of Diffusionless Electrochemical Systems J. Electroanal. Chem. Interfacial Electrochem. 1979, 101, 19-28 10.1016/S0022-0728(79)80075-3
56. Fabre, B.; Hauquier, F. Single-Component and Mixed Ferrocene-Terminated Alkyl Monolayers Covalently Bound to Si(111) Surfaces J. Phys. Chem. B 2006, 110, 6848-6855 10.1021/jp055698n
57. Hapiot, P.; Lagrost, C. Electrochemical Reactivity in Room-Temperature Ionic Liquids Chem. Rev. 2008, 108, 2238-2264 10.1021/cr0680686
58. Gooding, R.; Lillya, C. P.; Chien, C. W. Poly(Ferrocenylene Vinylene Phenylene Vinylene). A Photoactive Semiconductor J. Chem. Soc., Chem. Commun. 1983, 4, 151-153 10.1039/c39830000151
59. Mazurowski, M.; Gallei, M.; Li, J.; Didzoleit, H.; Stühn, B.; Rehahn, M. Redox-Responsive Polymer Brushes Grafted from Polystyrene Nanoparticles by Means of Surface Initiated Atom Transfer Radical Polymerization Macromolecules 2012, 45, 8970-8981 10.1021/ma3020195
60. Inzelt, G. Role of Polymeric Properties in the Electrochemical Behaviour of Redox Polymer-Modified Electrodes Electrochim. Acta 1989, 34, 83-91 10.1016/0013-4686(89)87071-9
61. Tam, T. K.; Pita, M.; Motornov, M.; Tokarev, I.; Minko, S.; Katz, E. Electrochemical Nanotransistor from Mixed-Polymer Brushes Adv. Mater. 2010, 22, 1863-1866 10.1002/adma.200903610
62. Cheng, L.; Liu, A.; Peng, S.; Duan, H. Responsive Plasmonic Assemblies of Amphiphilic Nanocrystals at Oil-Water Interfaces ACS Nano 2010, 4, 6098-6104 10.1021/nn101685q
63. Ionov, L.; Minko, S.; Stamm, M.; Gohy, J. F.; Jerome, R.; Scholl, A. Reversible Chemical Patterning on Stimuli-Responsive Polymer Film: Environment-Responsive Lithography J. Am. Chem. Soc. 2003, 125, 8302-8306 10.1021/ja035560n
64. Ionov, L.; Minko, S. Mixed Polymer Brushes with Locking Switching ACS Appl. Mater. Interfaces 2012, 4, 483-489 10.1021/am201736t
65. Xin, B.; Hao, J. Reversibly Switchable Wettability Chem. Soc. Rev. 2010, 39, 769-782 10.1039/B913622C
66. Ghilane, J.; Trippé-Allard, G.; Lacroix, J. C. Grafting of Imidazolium Ion-Terminated Layer Using Electrochemical Reduction of Diazonium: Redox Active Counter Anion Exchange Within the Layer Electrochem. Commun. 2013, 27, 73-76 10.1016/j.elecom.2012.11.003
67. Alaejos, M. S.; García Montelongo, F. J. Application of Amperometric Biosensors to the Determination of Vitamins and α-Amino Acids Chem. Rev. 2004, 104, 3239-3266 10.1021/cr0304471
68. Lawrence, N. S.; Beckett, E. L.; Davis, J.; Compton, R. G. Advances in the Voltammetric Analysis of Small Biologically Relevant Compounds Anal. Biochem. 2002, 303, 1-16 10.1006/abio.2002.5584
69. Jin, G. P.; Lin, X. Q. The Electrochemical Behavior and Amperometric Determination of Tyrosine and Tryptophan at a Glassy Carbon Electrode Modified with Butyrylcholine Electrochem. Commun. 2004, 6, 454-460 10.1016/j.elecom.2004.03.006
70. Quintana, C.; Suárez, S.; Hernández, L. Nanostructures on Gold Electrodes for the Development of an L-Tyrosine Electrochemical Sensor Based on Host-Guest Supramolecular Interactions Sens. Actuators, B 2010, 149, 129-135 10.1016/j.snb.2010.06.011