Superlithiation of Organic Electrode Materials: The Case of Dilithium Benzenedipropiolate

Chemistry of Materials

Volumn 28, Issue 6, 2016, Pages 1920-1926

  Renault, Stéven ^a   Oltean, Viorica Alina ^a   Araujo, C Moyses ^b   Grigoriev, Anton ^b   Edström, Kristina ^a   Brandell, Daniel ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; ELECTROCHEMICAL ELECTRODES; ELECTRODES; LITHIUM; LITHIUM ALLOYS; LITHIUM COMPOUNDS; LITHIUM-ION BATTERIES;

CARBON-CARBON BOND; DILITHIUM; LITHIATION; NEGATIVE ELECTRODE MATERIAL; ORGANIC ELECTRODES; SECONDARY LITHIUM ION BATTERIES; SPECIFIC CAPACITIES;

DENSITY FUNCTIONAL THEORY;

EID: 84962054068     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.6b00267     Document Type: Article

References (34)

1. Tarascon, J.-M.; Armand, M. Issues and Challenges Facing Rechargeable Lithium Batteries Nature 2001, 414, 359-367 10.1038/35104644
2. Armand, M.; Tarascon, J.-M. Building Better Batteries Nature 2008, 451, 652-657 10.1038/451652a
3. Poizot, P.; Dolhem, F. Clean Energy New Deal for a Sustainable World: From Non-CO2 Generating Energy Sources to Greener Electrochemical Storage Devices Energy Environ. Sci. 2011, 4, 2003-2019 10.1039/c0ee00731e
4. Larcher, D.; Tarascon, J.-M. Towards Greener and More Sustainable Batteries for Electrical Energy Storage Nat. Chem. 2015, 7, 19-29 10.1038/nchem.2085
5. 6 Organic Electrode for Sustainable Li-Ion Batteries ChemSusChem 2008, 1, 348-355 10.1002/cssc.200700161
6. 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 10.1021/ja9024897
7. Press release: NEC Develops Ultra-thin Organic Radical Battery Compatible with IC Cards. http://www.nec.com/en/press/201203/global-20120305-04.html (accessed January 2016).
8. Song, Z.; Zhou, H. Towards Sustainable and Versatile Energy Storage Devices: an Overview of Organic Electrode Materials Energy Environ. Sci. 2013, 6, 2280-2301 10.1039/c3ee40709h
9. Liang, Y.; Tao, Z.; Chen, J. Organic Electrode Materials for Rechargeable Lithium Batteries Adv. Energy Mater. 2012, 2, 742-769 10.1002/aenm.201100795
10. Häupler, B.; Wild, A.; Schubert, U. S. Carbonyls: Powerful Organic Materials for Secondary Batteries Adv. Energy Mater. 2015, 5, 1402034 10.1002/aenm.201402034
11. Novák, P.; Müller, K.; Santhanam, K. S. V.; Haas, O. Electrochemically Active Polymers for Rechargeable Batteries Chem. Rev. 1997, 97, 207-282 10.1021/cr941181o
12. Poizot, P.; Dolhem, F.; Gaubicher, J.; Renault, S. Lithium Process Chemistry, Chapter 6-Perspectives in Lithium Batteries; Elsevier: Amsterdam, 2015; pp 191-232.
13. 6 Aromatic Ring Systems? Angew. Chem., Int. Ed. 2012, 51, 5147-5151 10.1002/anie.201109187
14. Han, X.; Yi, F.; Sun, T.; Sun, J. Synthesis and Electrochemical Performance of Li and Ni 1,4,5,8-naphthalenetetracarboxylates as Anodes for Li-Ion Batteries Electrochem. Commun. 2012, 25, 136-139 10.1016/j.elecom.2012.09.014
15. Luo, W.; Allen, M.; Raju, V.; Ji, X. An Organic Pigment as a High-Performance Cathode for Sodium-Ion Batteries Adv. Energy Mater. 2014, 4, 1400554 10.1002/aenm.201400554
16. Lee, H. H.; Park, Y.; Shin, K.-H.; Lee, K. T.; Hong, S. Y. Abnormal Excess Capacity of Conjugated Dicarboxylates in Lithium-Ion Batteries ACS Appl. Mater. Interfaces 2014, 6, 19118-19126 10.1021/am505090p
17. Wu, J.; Rui, X.; Wang, C.; Pei, W.-B.; Lau, R.; Yan, Q.; Zhang, Q. Nanostructured Conjugated Ladder Polymers for Stable and Fast Lithium Storage Anodes with High-Capacity Adv. Enegy Mater. 2015, 5, 1402189 10.1002/aenm.201402189
18. Wu, J.; Rui, X.; Long, G.; Chen, W.; Yan, Q.; Zhang, Q. Pushing Up Lithium Storage through Nanostructured Polyazaacene Analogues as Anode Angew. Chem., Int. Ed. 2015, 54, 7354-7358 10.1002/anie.201503072
19. Fei, H.; Liu, X.; Li, Z.; Feng, W. Metal Dicarboxylates: New Anode Materials for Lithium-Ion Batteries with Good Cycling Performance Dalton Trans. 2015, 44, 9909-9914 10.1039/C5DT00500K
20. Lee, H. H.; Park, Y.; Kim, S. H.; Yeon, S.-H.; Kwak, S. K.; Lee, K. T.; Hong, S. Y. Mechanistic Studies of Transition Metal-Terephthalate Coordination Complexes upon Electrochemical Lithiation and Delithiation Adv. Funct. Mater. 2015, 25, 4859-4866 10.1002/adfm.201501436
21. Kim, D. J.; Je, S. H.; Sampath, S.; Choi, J. W.; Coskun, A. Effect of N-Substitution in Naphthalenediimides on the Electrochemical Performance of Organic Rechargeable Batteries RSC Adv. 2012, 2, 7968-7970 10.1039/c2ra21239k
22. Walker, W.; Grugeon, S.; Vezin, H.; Laruelle, S.; Armand, M.; Wudl, F.; Tarascon, J.-M. Electrochemical Characterization of Lithium 4,4′-tolane-dicarboxylate for Use as a Negative Electrode in Li-Ion Batteries J. Mater. Chem. 2011, 21, 1615-1620 10.1039/C0JM03458D
23. Renault, S.; Brandell, D.; Gustafsson, T.; Edström, K. Improving the Electrochemical Performance of Organic Li-Ion Battery Electrodes Chem. Commun. 2013, 49, 1945-1947 10.1039/c3cc39065a
24. Renault, S.; Mihali, V. A.; Brandell, D. Optimizing the Electrochemical Performance of Water-Soluble Organic Li-Ion Battery Electrodes Electrochem. Commun. 2013, 34, 174-176 10.1016/j.elecom.2013.06.008
25. Renault, S.; Brandell, D.; Edström, K. Environmentally-Friendly Lithium Recycling From a Spent Organic Li-Ion Battery ChemSusChem 2014, 7, 2859-2867 10.1002/cssc.201402440
26. Mihali, V. A.; Renault, S.; Nyholm, L.; Brandell, D. Benzenediacrylates as Organic Battery Electrode Materials: Na Versus Li RSC Adv. 2014, 4, 38004-38011 10.1039/C4RA06288D
27. Park, K.; You, J.-M.; Jeon, S.; Lee, S. Palladium-Catalyzed Sonogashira Reaction for the Synthesis of Arylalkynecarboxylic Acids from Aryl Bromides at Low Temperature Eur. J. Org. Chem. 2013, 2013, 1973-1978 10.1002/ejoc.201201606
28. Saravanakumar, R.; Varghese, B.; Sankararaman, S. Hydrogen-Bond Network in Isomeric Phenylenedipropynoic Acids and Their DABCO Salts. Water Mediated Helical Hydrogen Bond Motifs CrystEngComm 2009, 11, 337-346 10.1039/B816658G
29. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100 10.1103/PhysRevA.38.3098
30. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789 10.1103/PhysRevB.37.785
31. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652 10.1063/1.464913
32. Jaguar; Schrodinger, LLC: New York, 2010.
33. Hehre, W. J.; Ditchfield, R.; Pople, J. A. Self-Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules J. Chem. Phys. 1972, 56, 2257-2261 10.1063/1.1677527
34. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. Self-Consistent Molecular Orbital Methods. XXIII. A Polarization-Type Basis Set for Second-Row Elements J. Chem. Phys. 1982, 77, 3654-3665 10.1063/1.444267