Polymer-pendant interactions in poly(pyrrol-3-ylhydroquinone): A solution for the use of conducting polymers at stable conditions

Journal of Physical Chemistry C

Volumn 117, Issue 45, 2013, Pages 23558-23567

  Karlsson, Christoffer ^a   Huang, Hao ^a   Strømme, Maria ^a   Gogoll, Adolf ^b   Sjödin, Martin ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE STORAGE CAPACITY; ELECTRIC ENERGIES; ELECTRODE MATERIAL; ENVIRONMENTALLY FRIENDLY ALTERNATIVES; LITHIUM-ION BATTERY; ORGANIC MOLECULES; POLYMER BACKBONES; SITU SPECTROELECTROCHEMISTRY;

CONDUCTING POLYMERS; DISSOLUTION; REDOX REACTIONS; SEMICONDUCTOR DOPING; SPECTROELECTROCHEMISTRY;

POLYPYRROLES;

EID: 84887870288     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp408567h     Document Type: Article

References (45)

1. Scrosati, B. Nanomaterials: Paper Powers Battery Breakthrough Nat. Nanotechnol. 2007, 2, 598-599
2. Armand, M.; Tarascon, J.-M. Building Better Batteries Nature 2008, 451, 652-657
3. Notter, D. A.; Gauch, M.; Widmer, R.; Wäger, P.; Stamp, A.; Zah, R.; Althaus, H.-J. Contribution of Li-Ion Batteries to the Environmental Impact of Electric Vehicles Environ. Sci. Technol. 2010, 44, 6550-6556
4. Yang, Z.; Zhang, J.; Kintner-Meyer, M. C. W.; Lu, X.; Choi, D.; Lemmon, J. P.; Liu, J. Electrochemical Energy Storage for Green Grid Chem. Rev. 2011, 111, 3577-3613
5. 2 Generating Energy Sources to Greener Electrochemical Storage Devices Energy Environ. Sci. 2011, 4, 2003-2019
6. Liang, Y.; Tao, Z.; Chen, J. Organic Electrode Materials for Rechargeable Lithium Batteries Adv. Energy Mater. 2012, 2, 742-769
7. Mohammadi, A.; Inganäs, O.; Lundström, I. Properties of Polypyrrole-Electrolyte-Polypyrrole Cells J. Electrochem. Soc. 1986, 133, 947-949
8. Novák, P.; Müller, K.; Santhanam, K. S. V.; Haas, O. Electrochemically Active Polymers for Rechargeable Batteries Chem. Rev. 1997, 97, 207-282
9. Ferraris, J. P.; Eissa, M. M.; Brotherston, I. D.; Loveday, D. C. Performance Evaluation of Poly 3-(Phenylthiophene) Derivatives as Active Materials for Electrochemical Capacitor Applications Chem. Mater. 1998, 10, 3528-3535
10. Sarukawa, T.; Yamaguchi, S.; Oyama, N. Electrochemical Behaviors of Hexathiadipentalene Ring, Dithiol Ring, and Methyl Sulfide Groups on Anthracene Derivatives Confined on Electrode J. Electrochem. Soc. 2010, 157, F196-F201
11. Li, J.; Zhan, H.; Zhou, L.; Deng, S.; Li, Z.; Zhou, Y. Aniline-Based Polyorganodisulfide Redox System of High Energy for Secondary Lithium Batteries Electrochem. Commun. 2004, 6, 515-519
12. Nakahara, K.; Iwasa, S.; Satoh, M.; Morioka, Y.; Iriyama, J.; Suguro, M.; Hasegawa, E. Rechargeable Batteries with Organic Radical Cathodes Chem. Phys. Lett. 2002, 359, 351-354
13. Suga, T.; Ohshiro, H.; Sugita, S.; Oyaizu, K.; Nishide, H. Emerging N-Type Redox-Active Radical Polymer for a Totally Organic Polymer-Based Rechargeable Battery Adv. Mater. 2009, 21, 1627-1630
14. Renault, S.; Geng, J.; Dolhem, F.; Poizot, P. Evaluation of Polyketones with N-Cyclic Structure as Electrode Material for Electrochemical Energy Storage: Case of Pyromellitic Diimide Dilithium Salt Chem. Commun. (Cambridge, U. K.) 2011, 47, 2414-2416
15. Liang, Y.; Zhang, P.; Chen, J. Function-Oriented Design of Conjugated Carbonyl Compound Electrodes for High Energy Lithium Batteries Chem. Sci. 2013, 4, 1330-1337
16. Burkhardt, S. E.; Bois, J.; Tarascon, J.-M.; Hennig, R. G.; Abruña, H. D. Li-Carboxylate Anode Structure-Property Relationships from Molecular Modeling Chem. Mater. 2013, 25, 132-141
17. Armand, M.; Grugeon, S.; Vezin, H.; Laruelle, S.; Ribière, P.; Poizot, P.; Tarascon, J.-M. Conjugated Dicarboxylate Anodes for Li-Ion Batteries Nat. Mater. 2009, 8, 120-125
18. Chen, H.; Armand, M.; Courty, M.; Jiang, M.; Grey, C. P.; Dolhem, F.; Tarascon, J.-M.; Poizot, P. Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery J. Am. Chem. Soc. 2009, 131, 8984-8988
19. Yao, M.; Yamazaki, S.-I.; Senoh, H.; Sakai, T.; Kiyobayashi, T. Crystalline Polycyclic Quinone Derivatives as Organic Positive-Electrode Materials for Use in Rechargeable Lithium Batteries Mater. Sci. Eng., B 2012, 177, 483-487
20. Karlsson, C.; Jämstorp, E.; Strømme, M.; Sjödin, M. Computational Electrochemistry Study of 16 Isoindole-4,7-Diones as Candidates for Organic Cathode Materials J. Phys. Chem. C 2012, 116, 3793-3801
21. Liang, Y.; Zhang, P.; Yang, S.; Tao, Z.; Chen, J. Fused Heteroaromatic Organic Compounds for High-Power Electrodes of Rechargeable Lithium Batteries Adv. Energy Mater. 2013, 3, 600-605
22. Pud, A. A. Stability and Degradation of Conducting Polymers in Electrochemical Systems Synth. Met. 1994, 66, 1-18
23. Park, D.-S.; Shim, Y.-B.; Park, S.-M. Degradation of Electrochemically Prepared Polypyrrole in Aqueous Sulfuric Acid J. Electrochem. Soc. 1993, 140, 609-614
24. Olsson, H.; Nyström, G.; Strømme, M.; Sjödin, M.; Nyholm, L. Cycling Stability and Self-Protective Properties of a Paper-Based Polypyrrole Energy Storage Device Electrochem. Commun. 2011, 13, 869-871
25. Nyström, G.; Strømme, M.; Sjödin, M.; Nyholm, L. Rapid Potential Step Charging of Paper-Based Polypyrrole Energy Storage Devices Electrochim. Acta 2012, 70, 91-97
26. Karlsson, C.; Gogoll, A.; Strømme, M.; Sjödin, M. Investigation of the Redox Chemistry of Isoindole-4,7-Diones J. Phys. Chem. C 2013, 117, 894-901
27. Handbook of Conducting Polymers; Skotheim, T. A.; Elsenbaumer, R. L.; Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998.
28. Nyholm, L.; Nyström, G.; Mihranyan, A.; Strømme, M. Toward Flexible Polymer and Paper-Based Energy Storage Devices Adv. Mater. 2011, 23, 3751-3769
29. Andrieux, C. P.; Audebert, P. First Electrochemical Study of a Modified Electrode Obtained from a 3-Functionalized Pyrrole Derivative J. Electroanal. Chem. Interfacial Electrochem. 1989, 261, 443-448
30. Audebert, P.; Bidan, G.; Lapkowski, M. Reduction by Two Successive One-Electron Transfers of Anthraquinone Units Bonded to Electrodeposited Poly(Pyrrole) Films J. Chem. Soc., Chem. Commun. 1986, 887-889
31. Foos, J. S.; Degnan, S. M.; Glennon, D. G.; Beebe, X. Polypyrroles Derivatized in the 3-Position with Dimethoxybenzene and Quinone Functionalities J. Electrochem. Soc. 1990, 137, 2530-2533
32. Inagaki, T.; Hunter, M.; Yang, X. Q.; Skotheim, T. A.; Lee, H. S.; Okamoto, Y. Electrochemical Polymerization of Pyrrole Derivatives Mol. Cryst. Liq. Cryst. Incorporating Nonlinear Opt. 1988, 160, 79-88
33. Kon, A. B.; Foos, J. S.; Rose, T. L. Synthesis and Properties of Poly(3-hydroquinonylpyrrole) Chem. Mater. 1992, 4, 416-424
34. Rose, T. L.; Kon, A. B.; Wang, F. High Charge Storage Conductive Polymer Abstr. Pap. Am. Chem. Soc. 1995, 209, 311-312
35. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. N -(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles J. Org. Chem. 1990, 55, 6317-6328
36. Alvarez, A.; Guzmán, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. Synthesis of 3-Arylpyrroles and 3-Pyrrolylacetylenes by Palladium-Catalyzed Coupling Reactions J. Org. Chem. 1992, 57, 1653-1656
37. Nadeau, J. M.; Swager, T. M. New ß-Linked Pyrrole Monomers: Approaches to Highly Stable and Conductive Electrochromic Polymers Tetrahedron 2004, 60, 7141-7146
38. Kim, J. J.; Amemiya, T.; Tryk, D. A.; Hashimoto, K.; Fujishima, A. Charge Transport Processes in Electrochemically Deposited Poly(pyrrole) and Poly(N -methylpyrrole) Thin Films J. Electroanal. Chem. 1996, 416, 113-119
39. Brédas, J.-L.; Street, G. B. Polarons, Bipolarons, and Solitons in Conducting Polymers Acc. Chem. Res. 1985, 18, 309-315
40. Čabala, R.; Škarda, J.; Potje-Kamloth, K. Spectroscopic Investigation of Thermal Treatment of Doped Polypyrrole Phys. Chem. Chem. Phys. 2000, 2, 3283-3291
41. Sjödin, M.; Ghanem, R.; Polivka, T.; Pan, J.; Styring, S.; Sun, L.; Sundström, V.; Hammarström, L. Tuning Proton Coupled Electron Transfer from Tyrosine: A Competition between Concerted and Step-Wise Mechanisms Phys. Chem. Chem. Phys. 2004, 6, 4851-4858
42. Zotti, G.; Martina, S.; Wegner, G.; Schlüter, A.-D. Well-Defined Pyrrole Oligomers: Electrochemical and UV/Vis Studies Adv. Mater. 1992, 4, 798-801
43. Berger, S.; Rieker, A. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; John Wiley & Sons: London, 1974; Vol. 1; pp 163-229.
44. Carter, M. K. Correlation of Electronic Transitions and Redox Potentials Measured for Pyrocatechol, Resorcinol, Hydroquinone, Pyrogallol, and Gallic Acid with Results of Semi-empirical Molecular Orbital Computations-A Useful Interpretation Tool J. Mol. Struct. 2007, 831, 26-36
45. Heeger, A. J.; Sariciftci, N. S.; Namdas, E. B. Semiconducting and Metallic Polymers; Oxford University Press: Oxford, U.K., 2010.