Conjugated polymer energy level shifts in lithium-ion battery electrolytes

ACS Applied Materials and Interfaces

Volumn 6, Issue 21, 2014, Pages 19347-19354

  Song, Charles Kiseok ^a   Eckstein, Brian J ^a   Tam, Teck Lip Dexter ^a   Trahey, Lynn ^b   Marks, Tobin J ^a,c  

^a NORTHWESTERN UNIVERSITY   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

^c Northwestern University   (United States)

Author keywords

conjugated polymer; cyclic voltammetry; electrolyte; electron affinity; lithium ion battery; organic photovoltaics

Indexed keywords

CONJUGATED POLYMERS; CYCLIC VOLTAMMETRY; ELECTROLYTES; ELECTRON AFFINITY; IONIZATION POTENTIAL; IONS; LITHIUM COMPOUNDS; LITHIUM METALLOGRAPHY; PHOTOIONIZATION; POLYMER FILMS; REDOX REACTIONS; SEMICONDUCTING FILMS; ULTRAVIOLET PHOTOELECTRON SPECTROSCOPY;

ELECTRON CHARGE; HOMO ENERGY LEVELS; LITHIUM IONS; ORGANIC PHOTOVOLTAICS; POLYMER ENERGIES; REDOX POTENTIALS; REFERENCE ELECTRODES;

LITHIUM-ION BATTERIES;

EID: 84910107551     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am505416m     Document Type: Article

References (57)

1. Nyholm, L.; Nystrom, G.; Mihranyan, A.; Stromme, M. Toward Flexible Polymer and Paper-Based Energy Storage Devices Adv. Mater. 2011, 23, 3751-3769
2. Mahapatra, S. S.; Yadav, S. K.; Yoo, H. J.; Cho, J. W. Highly Stretchable, Transparent and Scalable Elastomers with Tunable Dielectric Permittivity J. Mater. Chem. 2011, 21, 7686-7691
3. Manceau, M.; Angmo, D.; Jorgensen, M.; Krebs, F. C. ITO-Free Flexible Polymer Solar Cells: From Small Model Devices to Roll-to-Roll Processed Large Modules Org. Electron. 2011, 12, 566-574
4. Wolf, M. O.; Wrighton, M. S. Tunable Electron-Density at a Rhenium Carbonyl Complex Coordinated to the Conducting Polymer Poly[5,5′-(2-thienyl)-2,2′-bithiazole] Chem. Mater. 1994, 6, 1526-1533
5. Dang, M. T.; Hirsch, L.; Wantz, G. P3HT:PCBM, Best Seller in Polymer Photovoltaic Research Adv. Mater. 2011, 23, 3597-3602
6. Guo, X. G.; Zhou, N. J.; Lou, S. J.; Smith, J.; Tice, D. B.; Hennek, J. W.; Ortiz, R. P.; Navarrete, J. T. L.; Li, S. Y.; Strzalka, J.; Chen, L. X.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. Polymer Solar Cells with Enhanced Fill Factors Nat. Photonics 2013, 7, 825-833
7. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Bulk Heterojunction Solar Cells with Internal Quantum Efficiency Approaching 100% Nat. Photonics 2009, 3, 297-303
8. Liang, Y. Y.; Xu, Z.; Xia, J. B.; Tsai, S. T.; Wu, Y.; Li, G.; Ray, C.; Yu, L. P. For the Bright Future-Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4% Adv. Mater. 2010, 22, E135-E138
9. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Light-Emitting-Diodes Based on Conjugated Polymers Nature 1990, 347, 539-541
10. Han, T. H.; Lee, Y.; Choi, M. R.; Woo, S. H.; Bae, S. H.; Hong, B. H.; Ahn, J. H.; Lee, T. W. Extremely Efficient Flexible Organic Light-Emitting Diodes with Modified Graphene Anode Nat. Photonics 2012, 6, 105-110
11. Liu, Y.; Liu, M. S.; Jen, A. K.-Y. Synthesis and Characterization of a Novel and Highly Efficient Light-Emitting Polymer Acta Polym. 1999, 50, 105-108
12. Cheng, Y. J.; Liu, M. S.; Zhang, Y.; Niu, Y. H.; Huang, F.; Ka, J. W.; Yip, H. L.; Tian, Y. Q.; Jen, A. K. Y. Thermally Cross-Linkable Hole-Transporting Materials on Conducting Polymer: Synthesis, Characterization, and Applications for Polymer Light-Emitting Devices Chem. Mater. 2008, 20, 413-422
13. Lee, J.; Kaake, L. G.; Cho, J. H.; Zhu, X. Y.; Lodge, T. P.; Frisbie, C. D. Ion Gel-Gated Polymer Thin-Film Transistors: Operating Mechanism and Characterization of Gate Dielectric Capacitance, Switching Speed, and Stability J. Phys. Chem. C 2009, 113, 8972-8981
14. Sirringhaus, H.; Kawase, T.; Friend, R. H.; Shimoda, T.; Inbasekaran, M.; Wu, W.; Woo, E. P. High-Resolution Inkjet Printing of All-Polymer Transistor Circuits Science 2000, 290, 2123-2126
15. Choi, W.; Harada, D.; Oyaizu, K.; Nishide, H. Aqueous Electrochemistry of Poly(vinylanthraquinone) for Anode-Active Materials in High-Density and Rechargeable Polymer/Air Batteries J. Am. Chem. Soc. 2011, 133, 19839-19843
16. Song, Z.; Qian, Y.; Liu, X.; Zhang, T.; Zhu, Y.; Yu, H.; Otani, M.; Zhou, H. A Quinone Based Oligomeric Lithium Salt for Superior Li-Organic Battery Energy Environ. Sci. 2014, 10.1039/C4EE02575J
17. Zhu, L. M.; Niu, Y. J.; Cao, Y. L.; Lei, A. W.; Ai, X. P.; Yang, H. X. n-Type Redox Behaviors of Polybithiophene and Its Implications for Anodic Li and Na Storage Materials Electrochim. Acta 2012, 78, 27-31
18. Liu, G.; Xun, S. D.; Vukmirovic, N.; Song, X. Y.; Olalde-Velasco, P.; Zheng, H. H.; Battaglia, V. S.; Wang, L. W.; Yang, W. L. Polymers with Tailored Electronic Structure for High Capacity Lithium Battery Electrodes Adv. Mater. 2011, 23, 4679-4683
19. Wu, M. Y.; Xiao, X. C.; Vukmirovic, N.; Xun, S. D.; Das, P. K.; Song, X. Y.; Olalde-Velasco, P.; Wang, D. D.; Weber, A. Z.; Wang, L. W.; Battaglia, V. S.; Yang, W. L.; Liu, G. Toward an Ideal Polymer Binder Design for High-Capacity Battery Anodes J. Am. Chem. Soc. 2013, 135, 12048-12056
20. Xun, S. D.; Song, X. Y.; Battaglia, V.; Liu, G. Conductive Polymer Binder-Enabled Cycling of Pure Tin Nanoparticle Composite Anode Electrodes for a Lithium-Ion Battery J. Electrochem. Soc. 2013, 160, A849-A855
21. Etacheri, V.; Marom, R.; Elazari, R.; Salitra, G.; Aurbach, D. Challenges in the Development of Advanced Li-Ion Batteries: A Review Energy Environ. Sci. 2011, 4, 3243-3262
22. Goodenough, J. B. Evolution of Strategies for Modern Rechargeable Batteries Acc. Chem. Res. 2013, 46, 1053-1061
23. Goodenough, J. B.; Kim, Y. Challenges for Rechargeable Li Batteries Chem. Mater. 2010, 22, 587-603
24. Larcher, D.; Beattie, S.; Morcrette, M.; Edstroem, K.; Jumas, J. C.; Tarascon, J. M. Recent Findings and Prospects in the Field of Pure Metals as Negative Electrodes for Li-Ion Batteries J. Mater. Chem. 2007, 17, 3759-3772
25. Zhang, W. J. A Review of the Electrochemical Performance of Alloy Anodes for Lithium-Ion Batteries J. Power Sources 2011, 196, 13-24
26. y Host Materials (M = Ni, Mn) J. Electrochem. Soc. 2000, 147, 1322-1331
27. Xu, K.; von Cresce, A. Interfacing Electrolytes with Electrodes in Li Ion Batteries J. Mater. Chem. 2011, 21, 9849-9864
28. Verma, P.; Maire, P.; Novak, P. A Review of the Features and Analyses of the Solid Electrolyte Interphase in Li-Ion Batteries Electrochim. Acta 2010, 55, 6332-6341
29. Zhang, D.; Haran, B. S.; Durairajan, A.; White, R. E.; Podrazhansky, Y.; Popov, B. N. Studies on Capacity Fade of Lithium-Ion Batteries J. Power Sources 2000, 91, 122-129
30. Lange, I.; Blakesley, J. C.; Frisch, J.; Vollmer, A.; Koch, N.; Neher, D. Band Bending in Conjugated Polymer Layers Phys. Rev. Lett. 2011, 106, 216402
31. Lange, I.; Kniepert, J.; Pingel, P.; Dumsch, I.; Allard, S.; Janietz, S.; Scherf, U.; Neher, D. Correlation between the Open Circuit Voltage and the Energetics of Organic Bulk Heterojunction Solar Cells J. Phys. Chem. Lett. 2013, 4, 3865-3871
32. Lee, J. H.; Shin, J. H.; Song, J. Y.; Wang, W. F.; Schlaf, R.; Kim, K. J.; Yi, Y. Interface Formation between ZnO Nanorod Arrays and Polymers (PCBM and P3HT) for Organic Solar Cells J. Phys. Chem. C 2012, 116, 26342-26348
33. Djurovich, P. I.; Mayo, E. I.; Forrest, S. R.; Thompson, M. E. Measurement of the Lowest Unoccupied Molecular Orbital Energies of Molecular Organic Semiconductors Org. Electron. 2009, 10, 515-520
34. Chen, E. S.; Chen, E. C. M.; Sane, N.; Talley, L.; Kozanecki, N.; Shulze, S. Classification of Organic Molecules to Obtain Electron Affinities from Half Wave Reduction Potentials: The Aromatic Hydrocarbons J. Chem. Phys. 1999, 110, 9319-9329
35. D'Andrade, B. W.; Datta, S.; Forrest, S. R.; Djurovich, P.; Polikarpov, E.; Thompson, M. E. Relationship between the Ionization and Oxidation Potentials of Molecular Organic Semiconductors Org. Electron. 2005, 6, 11-20
36. Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications Adv. Mater. 2011, 23, 2367-2371
37. Pavlishchuk, V. V.; Addison, A. W. Conversion Constants for Redox Potentials Measured Versus Different Reference Electrodes in Acetonitrile Solutions at 25°C Inorg. Chim. Acta 2000, 298, 97-102
38. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd ed.; John Wiley & Sons: New York, 2001.
39. Hou, J. H.; Tan, Z. A.; Yan, Y.; He, Y. J.; Yang, C. H.; Li, Y. F. Synthesis and Photovoltaic Properties of Two-Dimensional Conjugated Polythiophenes with Bi(thienylenevinylene) Side Chains J. Am. Chem. Soc. 2006, 128, 4911-4916
40. Mccullough, R. D.; Williams, S. P. Toward Tuning Electrical and Optical-Properties in Conjugated Polymers Using Side-Chains: Highly Conductive Head-to-Tail, Heteroatom-Functionalized Polythiophenes J. Am. Chem. Soc. 1993, 115, 11608-11609
41. Blouin, N.; Michaud, A.; Leclerc, M. A Low-Bandgap Poly(2,7-carbazole) Derivative for Use in High-Performance Solar Cells Adv. Mater. 2007, 19, 2295-2300
42. Chen, Z. H.; Zheng, Y.; Yan, H.; Facchetti, A. Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors J. Am. Chem. Soc. 2009, 131, 8-9
43. Anderson, P. A. The Work Function of Lithium Phys. Rev. 1949, 75, 1205-1207
44. 2 Studied Using Photoemission Spectroscopy J. Phys. Chem. B 2003, 107, 2253-2261
45. Yi, Y.; Lyon, J. E.; Beerbom, M. M.; Schlaf, R. Characterization of Indium Tin Oxide Surfaces and Interfaces Using Low Intensity X-Ray Photoemission Spectroscopy J. Appl. Phys. 2006, 100, 093719
46. Song, C. K.; White, A. C.; Zeng, L.; Leever, B. J.; Clark, M. D.; Emery, J. D.; Lou, S. J.; Timalsina, A.; Chen, L. X.; Bedzyk, M. J.; Marks, T. J. Systematic Investigation of Organic Photovoltaic Cell Charge Injection/Performance Modulation by Dipolar Organosilane Interfacial Layers ACS Appl. Mater. Interfaces 2013, 5, 9224-9240
47. Ciszkowska, M.; Osteryoung, J. G. Voltammetry of Metals at Mercury Film Microelectrodes in the Absence and the Presence of Varying Concentrations of Supporting Electrolyte Anal. Chem. 1995, 67, 1125-1131
48. 2 (anatase). 2. Voltammetry on Nanoporous Films J. Phys. Chem. B 1997, 101, 7717-7722
49. Daum, P.; Murray, R. W. Charge-Transfer Diffusion Rates and Activity Relationships during Oxidation and Reduction of Plasma-Polymerized Vinylferrocene Films J. Phys. Chem. 1981, 85, 389-396
50. Kadish, K. M.; Morrison, M. M. Solvent and Substituent Effects on the Redox Reactions of Para-Substituted Tetraphenylporphyrin J. Am. Chem. Soc. 1976, 98, 3326-3328
51. Sawyer, D. T.; Chlericato, G.; Angelis, C. T.; Nanni, E. J.; Tsuchiya, T. Effects of Media and Electrode Materials on the Electrochemical Reduction of Dioxygen Anal. Chem. 1982, 54, 1720-1724
52. Eslami, M.; Zare, H. R.; Namazian, M. The Effect of Solvents on the Electrochemical Behavior of Homogentisic Acid J. Electroanal. Chem. 2014, 720-721, 76-83
53. Fleischmann, M.; Hendra, P. J.; Mcquilla, A. J. Raman-Spectra of Pyridine Adsorbed at a Silver Electrode Chem. Phys. Lett. 1974, 26, 163-166
54. Andreas, H. A.; Conway, B. E. Examination of the Double-Layer Capacitance of an High Specific-Area C-cloth Electrode as Titrated from Acidic to Alkaline pHs Electrochim. Acta 2006, 51, 6510-6520
55. Isse, A. A.; Gennaro, A. Absolute Potential of the Standard Hydrogen Electrode and the Problem of Interconversion of Potentials in Different Solvents J. Phys. Chem. B 2010, 114, 7894-7899
56. Trasatti, S. The "Absolute" Electrode Potential-The End of the Story Electrochim. Acta 1990, 35, 269-271
57. Trasatti, S. The Absolute Electrode Potential: An Explanatory Note (Recommendations 1986) Pure Appl. Chem. 1986, 58, 955-966