Grafting of Quinones on Carbons as Active Electrode Materials in Electrochemical Capacitors

The electrochemical performance of electrochemical capacitors can be improved with electroactive quinone molecules. Systems based on redox active electrolyte as well as physisorbed and chemically grafted molecules have been investigated. In all these cases, carbon materials were used as substrate and electrode material. This short review will mainly describe work related to these systems and materials from the authors' laboratories. Nonetheless, some important studies from other research groups will be discussed.

Keywords:
electrochemical capacitors; quinone; diazonium; grafting; energy storage

Authorship

Thierry Brousse ^**e-mail: thierry.brousse@univ-nantes.fr; charles.cougnon@univ-angers.fr; belanger.daniel@uqam.ca

Institut des Matériaux Jean Rouxel, Université de Nantes, CNRS UMR 6502, 2 rue de la Houssinière BP32229, 44322 Nantes Cedex 3, FranceUniversité de NantesFranceNantes, FranceInstitut des Matériaux Jean Rouxel, Université de Nantes, CNRS UMR 6502, 2 rue de la Houssinière BP32229, 44322 Nantes Cedex 3, France

Réseau sur le Stockage Electrochimique de l'Energie, CNRS FR 3459, 80039 Amiens Cedex, FranceRéseau sur le Stockage Electrochimique de l'EnergieFranceAmiens, FranceRéseau sur le Stockage Electrochimique de l'Energie, CNRS FR 3459, 80039 Amiens Cedex, France

Thierry Brousse is a Professor of Materials Science at the University of Nantes. He received his PhD degree in 1991. After being a chemical engineer in a company, he joined the University of Nantes in 1994. His research at IMN focuses on innovative materials for electrochemical capacitors and related devices. He is Associate Editor for the Journal of The Electrochemical Society. He has mentored 23 PhD students. With his team as well as international collaborators, he co-authored more than 160 peer-reviewed journal publications and book chapters. He is currently vice-dean of the University of Nantes in charge of Technology Transfer.

Charles Cougnon ^**e-mail: thierry.brousse@univ-nantes.fr; charles.cougnon@univ-angers.fr; belanger.daniel@uqam.ca

Laboratoire MOLTECH-Anjou, Université d'Angers, UMR CNRS 6200, 2 bd Lavoisier, 49045 Angers Cedex, FranceUniversité d'AngersFranceAngers, FranceLaboratoire MOLTECH-Anjou, Université d'Angers, UMR CNRS 6200, 2 bd Lavoisier, 49045 Angers Cedex, France

Charles Cougnon was born in Royan, France, in 1974. He received his undergraduate education at the Universities of Poitiers and Rennes in France and obtained his PhD from the University of Rennes in 2002. Dr Cougnon joined the Centre National de la Recherche (CNRS) in 2003 as Chargé de Recherche. After having exercised in Le Mans up to 2008, he moved to the Université du Québec à Montréal (UQAM) as a visiting researcher in the group of Prof D. Bélanger. On his return to France in 2009, he joined the University of Angers. His research interests are centered on modified electrodes with particular recent emphasis on the electrochemical charge storage.

Daniel Bélanger ^**e-mail: thierry.brousse@univ-nantes.fr; charles.cougnon@univ-angers.fr; belanger.daniel@uqam.ca

Département de Chimie, Université du Québec à Montréal (UQAM), Case Postale 8888, succursale Centre-Ville, H3C 3P8 Montréal, Québec, CanadaUniversité du Québec à MontréalCanadaMontréal, Québec, CanadaDépartement de Chimie, Université du Québec à Montréal (UQAM), Case Postale 8888, succursale Centre-Ville, H3C 3P8 Montréal, Québec, Canada

Daniel Bélanger is currently Professor and holder of a “Chaire de recherche sur les nouveaux matériaux pour les technologies de l'énergie” in the Département de Chimie de l'Université du Québec à Montréal. His current research interests in the area of electrochemistry include chemical and electrochemical modification of surfaces and electrochemical energy storage and conversion systems. He has published over 185 publications, which have been cited more than 12000 times (h-index = 51, Scopus). He is currently Associate Editor for Electrochemistry Communications.

*e-mail: thierry.brousse@univ-nantes.fr; charles.cougnon@univ-angers.fr; belanger.daniel@uqam.ca

Thierry Brousse is a Professor of Materials Science at the University of Nantes. He received his PhD degree in 1991. After being a chemical engineer in a company, he joined the University of Nantes in 1994. His research at IMN focuses on innovative materials for electrochemical capacitors and related devices. He is Associate Editor for the Journal of The Electrochemical Society. He has mentored 23 PhD students. With his team as well as international collaborators, he co-authored more than 160 peer-reviewed journal publications and book chapters. He is currently vice-dean of the University of Nantes in charge of Technology Transfer.

Charles Cougnon was born in Royan, France, in 1974. He received his undergraduate education at the Universities of Poitiers and Rennes in France and obtained his PhD from the University of Rennes in 2002. Dr Cougnon joined the Centre National de la Recherche (CNRS) in 2003 as Chargé de Recherche. After having exercised in Le Mans up to 2008, he moved to the Université du Québec à Montréal (UQAM) as a visiting researcher in the group of Prof D. Bélanger. On his return to France in 2009, he joined the University of Angers. His research interests are centered on modified electrodes with particular recent emphasis on the electrochemical charge storage.

Daniel Bélanger is currently Professor and holder of a “Chaire de recherche sur les nouveaux matériaux pour les technologies de l'énergie” in the Département de Chimie de l'Université du Québec à Montréal. His current research interests in the area of electrochemistry include chemical and electrochemical modification of surfaces and electrochemical energy storage and conversion systems. He has published over 185 publications, which have been cited more than 12000 times (h-index = 51, Scopus). He is currently Associate Editor for Electrochemistry Communications.

SCIMAGO INSTITUTIONS RANKINGS

Figures

Figures (8)

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Scheme 1
Redox reactions of anthraquinone in acidic (top) and alkaline (bottom) electrolytes.¹⁰10 Le Comte, A.; Brousse, T.; Bélanger, D.; Electrochim. Acta 2014, 137, 447.

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Scheme 2
Chemical structure of electroactive molecules used for electrochemical capacitor applications. From left to right; aminocatechol, aminopyrene-4,5,9,10-tetraone, amino-9,10-anthraquinone, amino-9,10-phenanthrenequinone and their respective theoretical capacity.

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Figure 1
Cyclic voltammograms of unmodified Black Pearls (—) and anthraquinone modified Black Pearls carbon black recorded in 0.1 M H₂SO₄ at a scan rate of 10 mV s^-1. The loading of anthraquinone is 11 wt.% (- - -).¹⁴14 Pognon, G.; Brousse, T.; Demarconnay, L.; Bélanger, D.; J. Power Sources 2011, 196, 4117.^,¹⁹19 Pognon, G.; Brousse, T.; Bélanger, D.; Carbon 2011, 49, 1340. (Reprinted with permission from Elsevier).

Thumbnail

Scheme 3
Grafting reaction of anthraquinone diazonium ions with a carbon substrate by spontaneaous reduction of the diazonium cations.¹⁹19 Pognon, G.; Brousse, T.; Bélanger, D.; Carbon 2011, 49, 1340.

Thumbnail

Scheme 4
Schematic cyclic voltammograms of carbon-based electrodes in the potential range swept during operation as negative and positive electrode in an electrochemical capacitor. The figure on the right hand side shows the additional Faradaic contributions of suitable molecules for the negative (red) and positive (green) electrodes.

Thumbnail

Figure 2
Illustration of a fully organic asymmetric charge storage system composed of two carbon-based electrodes modified with N-(2-aminoethyl)-1,8-naphthalimide and 4-amino-2,2,6,6-tetramethylpiperidine-N-oxyl. Cyclic voltammograms were recorded in propylene carbonate + 1 M Bu₄NBF₄ at a scan rate of 1 mV s^-1 (curves in dotted lines refer to unmodified carbon electrodes). (Adapted from Lebègue et al.).⁴⁵45 Lebègue, E.; Brousse, T.; Gaubicher, J.; Retoux, R.; Cougnon, C.; J. Mater. Chem. A 2014, 2, 8599.

Thumbnail

Figure 3
Cyclic voltammograms of unmodified BP (solid line) and catechol-modified carbons using aminocatechol two different concentrations of the amine precursor for the grafting reaction (dashed lines for the modification with 0.1 eq and dotted lines for 0.2 eq).³⁶36 Pognon, G.; Cougnon, C.; Mayilukila, D.; Bélanger, D.; ACS Appl. Mater. Interfaces 2012, 4, 3788. (Reprinted with permission from American Chemical Society© 2012).

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Figure 4
Schematic representation of the cyclic voltammograms of both positive and negative electrode in: a carbon/carbon symmetric (top) and both carbon and phenanthrenequinone (PQ)-modified carbon as negative electrode and Ni(OH)₂ as positive electrode.⁵⁴54 Le Comte, A.; Brousse, T.; Bélanger, D.; J. Power Sources 2016, 326, 702. (Reprinted with permission from Elsevier).

Scheme 1 Redox reactions of anthraquinone in acidic (top) and alkaline (bottom) electrolytes.¹⁰10 Le Comte, A.; Brousse, T.; Bélanger, D.; Electrochim. Acta 2014, 137, 447.

Scheme 2 Chemical structure of electroactive molecules used for electrochemical capacitor applications. From left to right; aminocatechol, aminopyrene-4,5,9,10-tetraone, amino-9,10-anthraquinone, amino-9,10-phenanthrenequinone and their respective theoretical capacity.

Figure 1 Cyclic voltammograms of unmodified Black Pearls (—) and anthraquinone modified Black Pearls carbon black recorded in 0.1 M H₂SO₄ at a scan rate of 10 mV s^-1. The loading of anthraquinone is 11 wt.% (- - -).¹⁴14 Pognon, G.; Brousse, T.; Demarconnay, L.; Bélanger, D.; J. Power Sources 2011, 196, 4117.^,¹⁹19 Pognon, G.; Brousse, T.; Bélanger, D.; Carbon 2011, 49, 1340. (Reprinted with permission from Elsevier).

Scheme 3 Grafting reaction of anthraquinone diazonium ions with a carbon substrate by spontaneaous reduction of the diazonium cations.¹⁹19 Pognon, G.; Brousse, T.; Bélanger, D.; Carbon 2011, 49, 1340.

Scheme 4 Schematic cyclic voltammograms of carbon-based electrodes in the potential range swept during operation as negative and positive electrode in an electrochemical capacitor. The figure on the right hand side shows the additional Faradaic contributions of suitable molecules for the negative (red) and positive (green) electrodes.

Figure 2 Illustration of a fully organic asymmetric charge storage system composed of two carbon-based electrodes modified with N-(2-aminoethyl)-1,8-naphthalimide and 4-amino-2,2,6,6-tetramethylpiperidine-N-oxyl. Cyclic voltammograms were recorded in propylene carbonate + 1 M Bu₄NBF₄ at a scan rate of 1 mV s^-1 (curves in dotted lines refer to unmodified carbon electrodes). (Adapted from Lebègue et al.).⁴⁵45 Lebègue, E.; Brousse, T.; Gaubicher, J.; Retoux, R.; Cougnon, C.; J. Mater. Chem. A 2014, 2, 8599.

Figure 3 Cyclic voltammograms of unmodified BP (solid line) and catechol-modified carbons using aminocatechol two different concentrations of the amine precursor for the grafting reaction (dashed lines for the modification with 0.1 eq and dotted lines for 0.2 eq).³⁶36 Pognon, G.; Cougnon, C.; Mayilukila, D.; Bélanger, D.; ACS Appl. Mater. Interfaces 2012, 4, 3788. (Reprinted with permission from American Chemical Society© 2012).

Figure 4 Schematic representation of the cyclic voltammograms of both positive and negative electrode in: a carbon/carbon symmetric (top) and both carbon and phenanthrenequinone (PQ)-modified carbon as negative electrode and Ni(OH)₂ as positive electrode.⁵⁴54 Le Comte, A.; Brousse, T.; Bélanger, D.; J. Power Sources 2016, 326, 702. (Reprinted with permission from Elsevier).

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Grafting of Quinones on Carbons as Active Electrode Materials in Electrochemical Capacitors

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[1] *e-mail: thierry.brousse@univ-nantes.fr; charles.cougnon@univ-angers.fr; belanger.daniel@uqam.ca