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http://dx.doi.org/10.5012/bkcs.2014.35.11.3143

The Electrochemical Reaction Mechanism and Applications of Quinones  

Kim, R. Soyoung (Department of Chemistry, Seoul National University)
Chung, Taek Dong (Department of Chemistry, Seoul National University)
Publication Information
Abstract
This tutorial review provides a general account of the electrochemical behavior of quinones and their various applications. Quinone electrochemistry has been investigated for a long time due to its complexity. A simple point of view is developed that considers the relative stability of the reduced quinone species and the values of the first and second reduction potentials. The 9-membered square scheme in buffered aqueous solutions is explained and semiquinone radical stability is discussed in this context. Quinone redox reaction has also been employed in various studies. Diverse examples are presented under three broad categories defined by the roles of quinone: molecular tool for physical chemistry, versatile electron mediator, and charge storage for energy conversion devices.
Keywords
Quinone electrochemistry; 9-Membered square scheme; Semiquinone radical; Electron mediator; Organic electrode material;
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1 Li, Q.; Batchelor-McAuley, C.; Lawrence, N. S.; Hartshorne, R. S.; Compton, R. G. Chem. Commun. 2011, 11426.
2 Kim, Y.-R.; Kim, R. S.; Kang, S. K.; Choi, M. G.; Kim, H. Y.; Cho, D.; Lee, J. Y.; Chang, S.-K.; Chung, T. D. J. Am. Chem. Soc. 2013, 135, 18957.   DOI   ScienceOn
3 Sato, A.; Takagi, K.; Kano, K.; Kato, N.; Duine, J.; Ikeda, T. Biochem. J. 2001, 357, 893.   DOI
4 Buchachenko, A. L. Pure Appl. Chem. 2000, 72, 2243.
5 Roginsky, V.; Barsukova, T. J. Chem. Soc. Perkin Trans. 2 2000, 1575.
6 Lebedev, A. V.; Ivanova, M. V.; Ruuge, E. K. Arch. Biochem. Biophys. 2003, 413, 191.   DOI
7 Lebedev, A. V.; Ivanova, M. V.; Timoshin, A. A.; Ruuge, E. K. ChemPhysChem 2007, 8, 1863.   DOI   ScienceOn
8 O'Malley, P. J. J. Phys. Chem. A 1998, 102, 248.   DOI   ScienceOn
9 Kaupp, M.; Remenyi, C.; Vaara, J.; Malkina, O. L.; Malkin, V. G. J. Am. Chem. Soc. 2002, 124, 2709.   DOI   ScienceOn
10 Kwon, Y.; Mrksich, M. J. Am. Chem. Soc. 2002, 124, 806.   DOI   ScienceOn
11 Zhao, X.; Imahori, H.; Zhan, C.-G.; Sakata, Y.; Iwata, S.; Kitagawa, T. J. Phys. Chem. A 1997, 101, 622.   DOI   ScienceOn
12 Ma, W.; Long, Y.-T. Chem. Soc. Rev. 2013, 43, 30.
13 Kim, R. S.; Park, W.; Hong, H.; Chung, T. D.; Kim, S. Electrochem. Commun. 2014, 41, 39.   DOI   ScienceOn
14 Abhayawardhana, A. D.; Sutherland, T. C. J. Phys. Chem. C 2009, 113, 4915.
15 Chung, T. D.; Anson, F. C. Anal. Chem. 2001, 73, 337.   DOI   ScienceOn
16 Henstridge, M. C.; Wildgoose, G. G.; Compton, R. G. Langmuir 2010, 26, 1340.   DOI   ScienceOn
17 Bae, J. H.; Kim, Y.-R.; Kim, R. S.; Chung, T. D. Phys. Chem. Chem. Phys. 2013, 15, 10645.   DOI   ScienceOn
18 Trammell, S. A.; Seferos, D. S.; Moore, M.; Lowy, D. A.; Bazan, G. C.; Kushmerick, J. G.; Lebedev, N. Langmuir 2007, 23, 942.   DOI   ScienceOn
19 Trammell, S. A.; Moore, M.; Schull, T. L.; Lebedev, N. J. Electroanal. Chem. 2009, 628, 125.   DOI   ScienceOn
20 Hong, H.-G.; Park, W. Bull. Korean Chem. Soc. 2005, 26, 1885.   DOI   ScienceOn
21 Razzaq, H.; Qureshi, R.; Schiffrin, D. J. Electrochem. Commun. 2014, 39, 9.   DOI   ScienceOn
22 Petrangolini, P.; Alessandrini, A.; Berti, L.; Facci, P. J. Am. Chem. Soc. 2010, 132, 7445.   DOI   ScienceOn
23 Darwish, N.; Diez-Perez, I.; Guo, S.; Tao, N.; Gooding, J. J.; Paddon-Row, M. N. J. Phys. Chem. C 2012, 116, 21093.   DOI   ScienceOn
24 Tse, D. C.-S.; Kuwana, T. Anal. Chem. 1978, 50, 1315.   DOI
25 Petrangolini, P.; Alessandrini, A.; Navacchia, M. L.; Capobianco, M. L.; Facci, P. J. Phys. Chem. C 2011, 115, 19971.   DOI   ScienceOn
26 Petrangolini, P.; Alessandrini, A.; Facci, P. J. Phys. Chem. C 2013, 117, 17451.   DOI   ScienceOn
27 Carlson, B. W.; Miller, L. L. J. Am. Chem. Soc. 1985, 107, 479.   DOI
28 Murthy, A. S. N.; Sharma, J. Talanta 1998, 45, 951.   DOI   ScienceOn
29 Katz, E.; Lotzbeyer, T.; Schlereth, D. D.; Schuhmann, W.; Schmidt, H.-L. J. Electroanal. Chem. 1994, 73, 189.
30 Zhang, J.; Seo, K.; Jeon, I. C. Anal. Bioanal. Chem. 2003, 375, 539.
31 Umezawa, N.; Tsurunari, M.; Kondo, T. Chem. Lett. 2009, 38, 766.   DOI   ScienceOn
32 Willner, I.; Riklin, A. Anal. Chem. 1994, 66, 1535.   DOI   ScienceOn
33 Bardea, A.; Katz, E.; Buckmann, A. F.; Willner, I. J. Am. Chem. Soc. 1997, 119, 9114.   DOI
34 Willner, I.; Katz, E. Angew. Chem. Int. Ed. 2000, 39, 1180.   DOI   ScienceOn
35 Yehezkeli, O.; Tel-Vered, R.; Wasserman, J.; Trifonov, A.; Michaeli, D.; Nechushtai, R.; Willner, I. Nat. Commun. 2012, 3, 742.   DOI   ScienceOn
36 Piro, B.; Reisberg, S.; Anquetin, G.; Duc, H.-T.; Pham, M.-C. Biosensors 2013, 3, 58.   DOI   ScienceOn
37 March, G.; Noel, V.; Piro, B.; Reisberg, S.; Pham, M.-C. J. Am. Chem. Soc. 2008, 130, 15752.   DOI   ScienceOn
38 March, G.; Reisberg, S.; Piro, B.; Pham, M.-C.; Delamar, M.; Noel, V.; Odenthal, K.; Hibbert, D. B.; Gooding, J. J. J. Electroanal. Chem. 2008, 622, 37.   DOI   ScienceOn
39 Yeo, W.-S.; Mrksich, M. Angew. Chem. Int. Ed. 2003, 42, 3121.   DOI   ScienceOn
40 Akanda, M. R.; Tamilavan, V.; Park, S.; Jo, K.; Hyun, M. H.; Yang, H. Anal. Chem. 2013, 85, 1631.   DOI   ScienceOn
41 Aulenta, F.; Ferri, T.; Nicastro, D.; Majone, M.; Papini, M. P. New Biotechnol. 2011, 29, 126.   DOI   ScienceOn
42 Adachi, M.; Shimomura, T.; Komatsu, M.; Yakuwa, H.; Miya, A. Chem. Commun. 2008, 2055.
43 Ahmed, J.; Kim, S. Bull. Korean Chem. Soc. 2013, 34, 3649.   DOI   ScienceOn
44 Kim, E.; Leverage, W. T.; Liu, Y.; White, I. M.; Bentley, W. E.; Payne, G. F. Analyst 2013, 139, 32.
45 Song, Z.; Zhou, H. Energy Environ. Sci. 2013, 6, 2280.   DOI   ScienceOn
46 Alt, H.; Binder, H.; Kohling, A.; Sandstede, G. Electrochimica Acta 1972, 17, 873.   DOI   ScienceOn
47 Foos, J. S.; Erker, S. M.; Rembetsy, L. M. J. Electrochem. Soc. 1986, 133, 836.   DOI
48 Suematsu, S.; Naoi, K. J. Power Sources 2001, 97-98, 816.   DOI   ScienceOn
49 Le Gall, T.; Reiman, K. H.; Grossel, M. C.; Owen, J. R. J. Power Sources 2003, 119-121, 316.   DOI   ScienceOn
50 Choi, W.; Harada, D.; Oyaizu, K.; Nishide, H. J. Am. Chem. Soc. 2011, 133, 19839.   DOI   ScienceOn
51 Huskinson, B.; Marshak, M. P.; Suh, C.; Er, S.; Gerhardt, M. R.; Galvin, C. J.; Chen, X.; Aspuru-Guzik, A.; Gordon, R. G.; Aziz, M. J. Nature 2014, 505, 195.   DOI   ScienceOn
52 Roldan, S.; Blanco, C.; Granda, M.; Menendez, R.; Santamaria, R. Angew. Chem. - Int. Ed. 2011, 50, 1699.   DOI   ScienceOn
53 Roldan, S.; Granda, M.; Menendez, R.; Santamaria, R.; Blanco, C. J. Phys. Chem. C 2011, 115, 17606.   DOI   ScienceOn
54 Rausch, B.; Symes, M. D.; Cronin, L. J. Am. Chem. Soc. 2013, 135, 13656.   DOI   ScienceOn
55 Pichot, F.; Gregg, B. A. J. Phys. Chem. B 2000, 104, 6.
56 Cheng, M.; Yang, X.; Zhang, F.; Zhao, J.; Sun, L. Angew. Chem. Int. Ed. 2012, 51, 9896.   DOI   ScienceOn
57 Gunner, M. R.; Madeo, J.; Zhu, Z. J. Bioenerg. Biomembr. 2008, 40, 509.   DOI
58 Bolton, J. L.; Trush, M. A.; Penning, T. M.; Dryhurst, G.; Monks, T. J. Chem. Res. Toxicol. 2000, 13, 135.   DOI   ScienceOn
59 Moss, G. P.; Smith, P. A. S.; Tavernier, D. Pure Appl. Chem. 2009, 67, 1307.
60 Chambers, J. Q. The Chemistry of Quinonoid Compounds; Patai, S., Ed.; John Wiley & Sons: Ltd., pp 737-791.
61 Osyczka, A.; Moser, C. C.; Dutton, P. L. Trends Biochem. Sci. 2005, 30, 176.   DOI   ScienceOn
62 Hillard, E. A.; Abreu, F. C. de, Ferreira, D. C. M.; Jaouen, G.; Goulart, M. O. F.; Amatore, C. Chem. Commun. 2008, 2612.
63 Costentin, C.; Robert, M.; Saveant, J.-M. Chem. Rev. 2010, 110, PR1.   DOI   ScienceOn
64 Cabaniss, G. E.; Diamantis, A. A.; Murphy, W. R.; Linton, R. W.; Meyer, T. J. J. Am. Chem. Soc. 1985, 107, 1845.   DOI   ScienceOn
65 DuVall, S. H.; McCreery, R. L. Anal. Chem. 1999, 71, 4594.   DOI   ScienceOn
66 Forster, R. J.; O'Kelly, J. P. J. Electroanal. Chem. 2001, 498, 127.   DOI   ScienceOn
67 Chaudhari, V. R.; Bhat, M. A.; Ingole, P. P.; Haram, S. K. Electrochem. Commun. 2009, 11, 994.   DOI   ScienceOn
68 Aguilar-Martinez, M.; Macias-Ruvalcaba, N. A.; Bautista-Martinez, J. A.; Gomez, M.; Gonzalez, F. J.; Gonzalez, I. Curr. Org. Chem. 2004, 8, 1721.   DOI   ScienceOn
69 Eggins, B. R.; Chambers, J. Q. J. Electrochem. Soc. 1970, 117, 186.   DOI
70 Gupta, N.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 6384.   DOI   ScienceOn
71 Gomez, M.; Gonzalez, F. J.; Gonzalez, I. J. Electroanal. Chem. 2005, 578, 193.   DOI   ScienceOn
72 Guin, P. S.; Das, S.; Mandal, P. C. Int. J. Electrochem. 2011, 2011, 1.
73 Hui, Y.; Chng, E. L. K.; Chng, C. Y. L.; Poh, H. L.; Webster, R. D. J. Am. Chem. Soc. 2009, 131, 1523.   DOI   ScienceOn
74 Eigen, M. Discuss. Faraday Soc. 1965, 39, 7.   DOI
75 Quan, M.; Sanchez, D.; Wasylkiw, M. F.; Smith, D. K. J. Am. Chem. Soc. 2007, 129, 12847.   DOI   ScienceOn
76 Shim, Y.-B.; Park, S.-M. J. Electroanal. Chem. 1997, 425, 201.   DOI   ScienceOn
77 Laviron, E. J. Electroanal Chem Interfacial Electrochem. 1984, 164, 213.   DOI   ScienceOn
78 Bailey, S. I.; Ritchie, I. M. Electrochimica Acta 1985, 30, 3.   DOI
79 Song, Y.; Buettner, G. R. Free Radic. Biol. Med. 2010, 49, 919.   DOI   ScienceOn
80 Roginsky, V. A.; Pisarenko, L. M.; Bors, W.; Michel, C. J. Chem. Soc. Perkin Trans. 2 1999, 871.
81 Hong, H.-G.; Park, W. Langmuir 2001, 17, 2485.   DOI   ScienceOn
82 Trammell, S. A.; Lebedev, N. J. Electroanal. Chem. 2009, 632, 127.   DOI   ScienceOn
83 Lemmer, C.; Bouvet, M.; Meunier-Prest, R. Phys. Chem. Chem. Phys. 2011, 13, 13327.   DOI   ScienceOn
84 Laviron, E. J. Electroanal. Chem. Interfacial Electrochem. 1983, 146, 15.   DOI   ScienceOn
85 Laviron, E. J. Electroanal. Chem. 1979, 101, 19.   DOI   ScienceOn
86 Zhang, W.; Burgess, I. J. Phys. Chem. Chem. Phys. 2011, 13, 2151.   DOI   ScienceOn
87 Marchal, D.; Boireau, W.; Laval, J. M.; Bourdillon, C.; Moiroux, J. J. Electroanal. Chem. 1998, 451, 139.   DOI   ScienceOn
88 Batchelor-McAuley, C.; Li, Q.; Dapin, S. M.; Compton, R. G. J. Phys. Chem. B 2010, 114, 4094.   DOI   ScienceOn
89 Costentin, C.; Louault, C.; Robert, M.; Saveant, J.-M. Proc. Natl. Acad. Sci. 2009, 106, 18143.   DOI   ScienceOn
90 Bae, J. H.; Kim, Y.-R.; Kim, R. S.; Chung, T. D. Phys. Chem. Chem. Phys. 2013, 15, 10645.   DOI   ScienceOn
91 Medina-Ramos, J.; Oyesanya, O.; Alvarez, J. C. J. Phys. Chem. C 2013, 117, 902.   DOI
92 Song, N.; Gagliardi, C. J.; Binstead, R. A.; Zhang, M.-T.; Thorp, H.; Meyer, T. J. J. Am. Chem. Soc. 2012, 134, 18538.   DOI   ScienceOn
93 Moncelli, M. R.; Herrero, R.; Becucci, L.; Guidelli, R. Biochim. Biophys. Acta BBA - Bioenerg. 1998, 1364, 373.   DOI   ScienceOn
94 Gamage, R. S. K. A.; McQuillan, A. J.; Peake, B. M. J. Chem. Soc. Faraday Trans. 1991, 87, 3653.   DOI
95 Trammell, S. A.; Lowy, D. A.; Seferos, D. S.; Moore, M.; Bazan, G. C.; Lebedev, N. J. Electroanal. Chem. 2007, 606, 33.   DOI   ScienceOn
96 Bailey, S. I.; Ritchie, I. M.; Hewgill, F. R. J. Chem. Soc. Perkin Trans. 2 1983, 645.
97 Anxolabehere-Mallart, E.; Costentin, C.; Policar, C.; Robert, M.; Saveant, J.-M.; Teillout, A.-L. Faraday Discuss. 2010, 148, 83.
98 Darwish, N.; Eggers, P. K.; Ciampi, S.; Tong, Y.; Ye, S.; Paddon- Row, M. N.; Gooding, J. J. J. Am. Chem. Soc. 2012, 134, 18401.   DOI   ScienceOn
99 He, X.-P.; Wang, X.-W.; Jin, X.-P.; Zhou, H.; Shi, X.-X.; Chen, G.- R.; Long, Y.-T. J. Am. Chem. Soc. 2011, 133, 3649.   DOI   ScienceOn
100 Feng, C.; Ma, L.; Li, F.; Mai, H.; Lang, X.; Fan, S. Biosens. Bioelectron. 2010, 25, 1516.   DOI   ScienceOn
101 Yu, H.; Wu, J.; Fan, L.; Lin, Y.; Xu, K.; Tang, Z.; Cheng, C.; Tang, S.; Lin, J.; Huang, M. et al. J. Power Sources 2012, 198, 402.   DOI   ScienceOn
102 Chambers, J. Q. The Chemistry of Quinonoid Compounds; Patai, S., Rappaport, Z., Eds.; Great Britain: John Wiley & Sons: pp 719-757.