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Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.ORCID iD: 0000-0002-5496-9664
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
2012 (English)In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 116, no 5, 3793-3801 p.Article in journal (Refereed) Published
Abstract [en]

Prediction of the redox behavior of electroactive molecules enables screening of a variety of compounds and can serve as a guideline in the search for organic molecules for use as cathode materials in, for example, Li ion batteries. In this study, we present a computational strategy, based on density functional theory, to calculate redox potentials and acid dissociation constants for a series of 16 isoindole-4,7-dione (IID) derivatives. The calculations take all possible electron and proton transfers into account, and the results were found to correlate very well with electrochemical and spectroscopic measurements. The possibility of polymerizing the IID derivatives was also assessed computationally, as polymerization serves as a straightforward route to immobilize the active material. Three of the considered IIDs (5,6-dicyano-2-methyl-isoindole-4,7-dione, 5,6-dihydroxy-2-methyl-isoindole-4,7-dione, and 2-methyl-5-(trifluoromethyl)-isoindole-4,7-dione) are predicted to be particularly interesting for making polymers for organic cathodes because these are calculated to have high redox potentials and high specific capacities and to be readily polymerizable. The presented strategy is general and can be applied in the prediction of the electrochemical behavior of quinones as well as other systems involving proton and electron transfers.

Place, publisher, year, edition, pages
American Chemical Society , 2012. Vol. 116, no 5, 3793-3801 p.
National Category
Other Chemistry Topics Nano Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
URN: urn:nbn:se:uu:diva-168889DOI: 10.1021/jp211851fISI: 000299985300073OAI: oai:DiVA.org:uu-168889DiVA: diva2:503877
Available from: 2012-02-17 Created: 2012-02-17 Last updated: 2017-12-07Bibliographically approved
In thesis
1. Conducting Redox Polymers for Electrical Energy Storage: Backbone - Substituent Interactions in Quinone Polypyrrole Model Systems
Open this publication in new window or tab >>Conducting Redox Polymers for Electrical Energy Storage: Backbone - Substituent Interactions in Quinone Polypyrrole Model Systems
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Organic electrical energy storage (EES) is a growing field of research that is expected to play an important role in the future, as the need for sustainable EES increases. Conducting redox polymers (CRPs), i.e. conducting polymers with incorporated redox active moieties e.g. as pendant groups (PGs), are proposed as a promising class of compounds for this purpose. Redox cycling of the PGs can be utilized for high charge storage capacity, while the conducting polymer backbone provides fast charge transport through the material. Some of the major challenges with small-molecule systems for EES could be solved by using CRPs, e.g. capacity fading due to dissolution of the active compound, and high resistance due to slow charge transport between molecules. The latter issue is often solved by adding large amounts of conducting additives to the active material, drastically lowering the specific capacity. In this project, CRPs are shown to be able to function in battery cells without any additives, making both high capacity and high power possible. Although several CRPs have been reported in the literature, very few detailed studies have been conducted on the electrochemical processes of the two systems (i.e. the conducting polymer backbone and the redox active PGs). An important factor to consider in CRP design is the possibility for interaction between the two redox systems, which could be either beneficial or detrimental to the function as EES material. In this thesis, CRP model systems composed of hydroquinone functionalized polypyrrole have been studied, and they exhibit separate redox reactions for the PGs and the backbone, overlapping in potential. Significant interaction between them was observed, as oxidation of the PGs has severe impact on the backbone: When the oxidized and hydrophobic p-benzoquinone PGs are formed, they pack and force the polymer backbone to twist, localizing the bipolarons, and decreasing the conductivity. This is accompanied by a contraction of the polymer film and expulsion of electrolyte. Overall, the interaction in these polymers is destructive for their EES function, and it could be eliminated by introduction of a long linker unit between the PGs and the backbone.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2014. 72 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1177
Keyword
Organic energy storage, Hydroquinone polymers, Functionalized polypyrrole, Spectroelectrochemistry, Electrochemical quartz crystal microbalance, In situ conductivity
National Category
Nano Technology
Identifiers
urn:nbn:se:uu:diva-230647 (URN)978-91-554-9033-1 (ISBN)
Public defence
2014-10-30, Polhemssalen, Ångströmslaboratoriet, Lägerhyddsvägen 1, Uppsala, 13:30 (English)
Opponent
Supervisors
Available from: 2014-10-03 Created: 2014-08-27 Last updated: 2015-01-23Bibliographically approved

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Karlsson, ChristofferJämstorp, ErikStrømme, MariaSjödin, Martin

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