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Rechargeable organic batteries using chloro-substituted naphthazarin derivatives as positive electrode materials

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Abstract

The use of redox active organic compounds as an alternative positive electrode material of rechargeable lithium batteries can be a solution for the resource issues of the current battery system. To satisfy both the high capacity and long cycle life of the batteries using organic active materials, naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) derivatives, which potentially exhibit a four-electron transfer redox reaction, were investigated. While the unsubstituted naphthazarin lithium salt (1), having a high theoretical capacity of up to about 550 mAh g−1, showed only half the expected capacity and a short cycle life as a positive electrode active material, the chloro-substituted ones (1-Cl 2 , 1-Cl 4 ) exhibited improved properties in both their initial capacity utilization and cycle life. In addition, the high stability of a chloro-substituted naphthazarin salt (1-Cl 4 ) was supported by a reversible electrochromic behavior during the redox reaction. The substituent effect of the naphthazarin derivatives on the cycle stability was discussed with respect to the battery performance and electrochromic behavior. Also, a guide for designing a new organic active material which shows a high capacity and long cycle life is suggested.

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References

  1. Novák P, Müller K, Santhanam SV, Hass O (1997) Electrochemically active polymers for rechargeable batteries. Chem Rev 97:207–281

    Article  Google Scholar 

  2. Armand M, Tarascon JM (2008) Building better batteries. Nature 451:652–657

    Article  Google Scholar 

  3. Nishide H, Oyaizu K (2008) Toward flexible batteries. Science 319:737–738

    Article  Google Scholar 

  4. Nakahara K, Iwasa S, Satoh M, Morioka Y, Suguro M, Hasegawa E (2002) Rechargeable batteries with organic radical cathodes. Chem Phys Lett 359:351–354

    Article  Google Scholar 

  5. Yoshikawa H, Kazama C, Awaga K, Satoh M, Wada J (2007) Rechargeable molecular cluster batteries. Chem Commun 30:3169–3170

    Article  Google Scholar 

  6. Chen H, Armand M, Demailly G, Dolhem F, Poizot P, Tarascon JM (2008) From biomass to a renewable LixC6O6 organic electrode for sustainable Li-ion batteries. ChemSusChem 1:348–355

    Article  Google Scholar 

  7. Inatomi Y, Hojo N, Yamamoto T, Watanabe S, Misaki Y (2012) Construction of rechargeable batteries using multifused tetrathiafulvalene systems as cathode materials. ChemPlusChem 77:973–976

    Article  Google Scholar 

  8. Matsunaga T, Kubota T, Sugimoto T, Satoh M (2011) High-performance lithium secondary batteries using cathode active materials of triquinoxalinylenes exhibiting six electron migration. Chem Lett 40:750–752

    Article  Google Scholar 

  9. Morita Y, Nishida S, Murata T, Moriguchi M, Ueda A, Satoh M, Arifuku K, Sato K, Takui T (2011) Organic tailored batteries materials using stable open-shell molecules with degenerate frontier orbitals. Nat Mater 10:947–951

    Article  Google Scholar 

  10. Yokoji T, Matsubara H, Satoh M (2014) Rechargeable organic lithium-ion batteries using electron-deficient benzoquinones as positive-electrode materials with high discharge voltages. J Mater Chem A 2:19347–19354

    Article  Google Scholar 

  11. Yokoji T, Kameyama Y, Sakaida S, Maruyama N, Satoh M, Matsubara H (2015) Steric effects on the cyclability of benzoquinone-type organic cathode active materials for rechargeable batteries. Chem Lett 44:1726–1728

    Article  Google Scholar 

  12. Yokoji T, Kameyama Y, Maruyama N, Matsubara H (2016) High-capacity organic cathode active materials of 2,2′-bis-p-benzoquinone derivatives for rechargeable batteries. J Mater Chem A 4:5457–5466

    Article  Google Scholar 

  13. Yao M, Senoh H, Yamazaki S, Siroma Z, Sakai T, Yasuda K (2010) High-capacity organic positive-electrode material based on a benzoquinone derivative for use in rechargeable lithium batteries. J Power Sources 195:8336–8340

    Article  Google Scholar 

  14. Yao M, Yamazaki S, Senoh H, Sakai T, Kiyobayashi T (2012) Crystalline polycyclic quinone derivatives as organic positive-electrode materials for use in rechargeable lithium batteries. Mater Sci Eng B 177:483–487

    Article  Google Scholar 

  15. Yao M, Ando H, Kiyobayashi T (2013) Dialkoxybenzoquinone-type active materials for rechargeable lithium batteries: the effect of the alkoxy group length on the cycle-stability. Energy Proc 34:880–887

    Article  Google Scholar 

  16. Yao M, Numoto T, Araki M, Ando H, Takeshita HT, Kiyobayashi T (2014) Long cycle-life organic electrode material based on an ionic naphthoquinone derivative for rechargeable batteries. Energy Proc 56:228–236

    Article  Google Scholar 

  17. Yao M, Numoto T, Ando H, Kondo R, Takeshita HT, Kiyobayashi T (2016) Improving the cycle-life of naphthoquinone-based active materials by their polymerization for rechargeable organic batteries. Energy Proc 89:213–221

    Article  Google Scholar 

  18. Ambrose JF, Carpenter LL, Nelson RF (1975) Electrochemical and spectroscopic properties of cation radicals III. Reaction pathways of carbazolium radical ions. J Electrochem Soc 122:876–894

    Article  Google Scholar 

  19. Yoshino S, Hayakawa K, Kanematsu K (1981) Reagent design and study of p-benzoquinone derivatives. Site-selective cycloaddition reaction of diquinones and photochemical cage formation of the adducts. J Org Chem 46:3841–3846

    Article  Google Scholar 

  20. Pochorovski I, Boudon C, Gisselbrecht JP, Ebert MO, Schweizer WB, Diederich F (2012) Quinone-based, redox-active resorcin [4] arene cavitands. Angew Chem 51:262–266

    Article  Google Scholar 

  21. Novikov VL, Balaneva NN, Shestak OP, Anufriev VP, Glazunov VP (2016) Cycloacylation of chloro-substituted hydroquinone dimethyl ethers with dichloromaleic anhydride. Russ Chem Bull Int Ed 65:993–1003

    Article  Google Scholar 

  22. Huot R, Brassard P (1974) Friedel-Crafts condensations with maleic anhydrides. III. The synthesis of polyhydroxylated naphthoquinones. Can J Chem 52:838–842

    Article  Google Scholar 

  23. Bruce DB, Thomson RH (1955) Quinones. Part V. The chemistry of naphthazarin. J Chem Soc 5:1089–1096

    Article  Google Scholar 

  24. Shimizu A, Kuramoto H, Tsujii Y, Nokami T, Inatomi Y, Hojo N, Suzuki H, Yoshida J (2014) Introduction of two lithiooxycarbonyl groups enhances cyclability of lithium batteries with organic cathode materials. J Power Sources 260:211–217

    Article  Google Scholar 

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Acknowledgements

We thank Ms. Miho Araki, AIST, for her technical support.

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Correspondence to Masaru Yao.

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Yao, M., Umetani, S., Ando, H. et al. Rechargeable organic batteries using chloro-substituted naphthazarin derivatives as positive electrode materials. J Mater Sci 52, 12401–12408 (2017). https://doi.org/10.1007/s10853-017-1368-z

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  • DOI: https://doi.org/10.1007/s10853-017-1368-z

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