Biologically inspired pteridine redox centres for rechargeable batteries

Nature Communications

Volumn 5, Issue , 2014, Pages

  Hong, Jihyun ^a   Lee, Minah ^b   Lee, Byungju ^a   Seo, Dong Hwa ^a,c   Park, Chan Beum ^b   Kang, Kisuk ^a  

^a Seoul National University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^c Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM; PTERIDINE DERIVATIVE; SODIUM; 7,8-DIMETHYLALLOXAZINE; RIBOFLAVIN DERIVATIVE;

AROMATIC HYDROCARBON; ELECTRODE; ENERGY CONSERVATION; INTEGRATED APPROACH; OPTIMIZATION; REDOX POTENTIAL;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ELECTRONICS; OXIDATION REDUCTION REACTION; RECHARGEABLE BATTERY; TAUTOMER; THEORETICAL STUDY; BIOENERGY; CHEMISTRY; ELECTRODE; EVALUATION STUDY;

BIOELECTRIC ENERGY SOURCES; ELECTRODES; FLAVINS; LITHIUM; OXIDATION-REDUCTION; PTERIDINES; SODIUM;

EID: 84923314849     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms6335     Document Type: Article

References (48)

1. Liang, Y., Tao, Z. & Chen, J. Organic electrode materials for rechargeable lithium batteries. Adv. Energy Mater. 2, 742-769 (2012).
2. Reddy, A. L. M. et al. Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes. Sci. Rep. 2, 960 (2012).
3. Song, Z. & Zhou, H. Towards sustainable and versatile energy storage devices: an overview of organic electrode materials. Energy Environ. Sci. 6, 2280-2301 (2013).
4. 2 generating energy sources to greener electrochemical storage devices. Energy Environ. Sci. 4, 2003-2019 (2011).
5. 6 organic electrode for sustainable Li-ion batteries. ChemSusChem 1, 348-355 (2008).
6. Milczarek, G. & Inganas, O. Renewable cathode materials from biopolymer/conjugated polymer interpenetrating networks. Science 335, 1468-1471 (2012).
7. Han, X., Chang, C., Yuan, L., Sun, T. & Sun, J. Aromatic carbonyl derivative polymers as high-performance Li-ion storage materials. Adv. Mater. 19, 1616-1621 (2007).
8. Song, Z., Zhan, H. & Zhou, Y. Polyimides: promising energy-storage materials. Angew. Chem. Int. Ed. 49, 8444-8448 (2010).
9. Huskinson, B. et al. A metal-free organic-inorganic aqueous flow battery. Nature 505, 195-198 (2014).
10. 6 nanosheets for lithium-ion batteries. Nano Lett. 13, 4404-4409 (2013).
11. Huang, W. et al. Quasi-solid-state rechargeable lithium-ion batteries with a calix[4]quinone cathode and gel polymer electrolyte. Angew. Chem. 125, 9332-9336 (2013).
12. Nishida, S., Yamamoto, Y., Takui, T. & Morita, Y. Organic rechargeable batteries with tailored voltage and cycle performance. ChemSusChem 6, 794-797 (2013).
13. Morita, Y. et al. Organic tailored batteries materials using stable open-shell molecules with degenerate frontier orbitals. Nat. Mater. 10, 947-951 (2011).
14. Lee, M. et al. Organic nanohybrids for fast and sustainable energy storage. Adv. Mater. 26, 2558-2565 (2014).
15. Wu, H. et al. Flexible and binder-free organic cathode for high-performance lithium-ion batteries. Adv. Mater. 26, 3338-3343 (2014).
16. Nokami, T. et al. Polymer-bound pyrene-4, 5, 9, 10-tetraone for fast-charge and-discharge lithium-ion batteries with high capacity. J. Am. Chem. Soc. 134, 19694-19700 (2012).
17. Luo, C. et al. Self-assembled organic nanowires for high power density lithium ion batteries. Nano Lett. 14, 1596-1602 (2014).
18. Kaim, W., Schwederski, B., Heilmann, O. & Hornung, F. M. Coordination compounds of pteridine, alloxazine and flavin ligands: structures and properties. Coord. Chem. Rev. 182, 323-342 (1999).
19. Sakai, K., Nagahara, K., Yoshii, Y., Hoshino, N. & Akutagawa, T. Structural and spectroscopic study of 6, 7-dicyano-substituted lumazine with high electron affinity and proton acidity. J. Phys. Chem. A 117, 3614-3624 (2013).
20. Miura, R. Versatility and specificity in flavoenzymes: control mechanisms of flavin reactivity. Chem. Rec. 1, 183-194 (2001).
21. Joosten, V. & van Berkel, W. J. H. Flavoenzymes. Curr. Opin. Chem. Biol. 11, 195-202 (2007).
22. Tan, S. L. J. & Webster, R. D. Electrochemically induced chemically reversible proton-coupled electron transfer reactions of riboflavin (vitamin B2). J. Am. Chem. Soc. 134, 5954-5964 (2012).
23. Lee, M. et al. Redox cofactor from biological energy transduction as molecularly tunable energy-storage compound. Angew. Chem. Int. Ed. 52, 8322-8328 (2013).
24. Sikorska, E. et al. Hydrogen-bonded complexes of lumichrome. J. Phys. Chem. A 109, 1785-1794 (2005).
25. Moyon, N. S. & Mitra, S. Fluorescence solvatochromism in lumichrome and excited-state tautomerization: a combined experimental and DFT study. J. Phys. Chem. A 115, 2456-2464 (2011).
26. Sikorska, E. et al. Ground-and excited-state double proton transfer in lumichrome/acetic acid system: theoretical and experimental approach. J. Phys. Chem. A 109, 11707-11714 (2005).
27. + ZSM-5 zeolites. Phys. Chem. Chem. Phys. 11, 5762-5772 (2009).
28. 2 +). J. Am. Chem. Soc. 135, 14532-14535 (2013).
29. Castillo-Martínez, E., Carretero-González, J. & Armand, M. Polymeric Schiff bases as low-voltage redox centers for sodium-ion batteries. Angew. Chem. Int. Ed. 53, 5341-5345 (2014).
30. Armand, M. et al. Conjugated dicarboxylate anodes for Li-ion batteries. Nat. Mater. 8, 120-125 (2009).
31. Bhargava, G., Ramanarayanan, T. A. & Bernasek, S. L. Imidazole-Fe interaction in an aqueous chloride medium: effect of cathodic reduction of the native oxide. Langmuir 26, 215-219 (2009).
32. Lee, T. H., Colton, R. J., White, M. G. & Rabalais, J. W. Electronic structure of hydrazoic acid and the azide ion from X-ray and ultraviolet electron spectroscopy. J. Am. Chem. Soc. 97, 4845-4851 (1975).
33. Takahashi, M., Ishikawa, Y., Nishizawa, J.-i. & Ito, H. Low-frequency vibrational modes of riboflavin and related compounds. Chem. Phys. Lett. 401, 475-482 (2005).
34. Wolf, M. M. N., Schumann, C, Gross, R., Domratcheva, T. & Diller, R. Ultrafast infrared spectroscopy of riboflavin: dynamics, electronic structure, and vibrational mode analysis. J. Phys. Chem. B 112, 13424-13432 (2008).
35. Liang, Y., Zhang, P. & Chen, J. Function-oriented design of conjugated carbonyl compound electrodes for high energy lithium batteries. Chem. Sci. 4, 1330-1337 (2013).
36. Song, Z. et al. Polymer-graphene nanocomposites as ultrafast-charge and-discharge cathodes for rechargeable lithium batteries. Nano Lett. 12, 2205-2211 (2012).
37. Kim, S.-W., Seo, D.-H., Ma, X., Ceder, G. & Kang, K. Electrode materials for rechargeable sodium-ion batteries: potential alternatives to current lithium-ion batteries. Adv. Energy Mater. 2, 710-721 (2012).
38. Yao, M. et al. Indigo carmine: an organic crystal as a positive-electrode material for rechargeable sodium batteries. Sci. Rep. 4, 3650 (2014).
39. Sakaushi, K. et al. Aromatic porous-honeycomb electrodes for a sodium-organic energy storage device. Nat. Commun. 4, 1485 (2013).
40. 6. Angew. Chem. 126, 6002-6006 (2014).
41. Frisch, M. et al. Gaussian 09 revision D. 01 (Gaussian Inc., 2009).
42. Lee, C., Yang, W. & Parr, R. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789 (1988).
43. Stephens, P. J., Devlin, F. J., Chabalowski, C. F. & Frisch, M. J. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem. 98, 11623-11627 (1994).
44. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652 (1993).
45. Schäfer, A., Huber, C. & Ahlrichs, R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J. Chem. Phys. 100, 5829-5835 (1994).
46. Schäfer, A., Horn, H. & Ahlrichs, R. Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J. Chem. Phys. 97, 2571-2577 (1992).
47. Klaumúnzer, B., Króner, D. & Saalfrank, P. (TD-) DFT calculation of vibrational and vibronic spectra of riboflavin in solution. J. Phys. Chem. B 114, 10826-10834 (2010).
48. Mulliken, R. S. Electronic population analysis on LCAO-MO molecular wave functions. I. J. Chem. Phys. 23, 1833-1840 (1955).