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Investigation of the Redox Chemistry of Isoindole-4,7-diones
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, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
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.
2013 (English)In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 117, no 2, 894-901 p.Article in journal (Refereed) Published
Abstract [en]

Quinone derivatives have been proposed as active components in lithium ion battery (LIB) electrode materials. In this work the electrochemistry of a series of substituted isoindole-4,7-diones (IIDs) was investigated. Three new IID derivatives were synthesized and characterized by various electrochemical and spectroscopic techniques. Polymerization was attempted to achieve a conducting polymer with redox active quinone side groups, which would be advantageous in a LIB application. A combination of in situ spectroelectrochemical measurements and density functional theory (DFT) calculations was used to investigate the proton coupled redox reactions of the IIDs. Results from a previous computational study of the IIDs were compared with experimental data here, and the agreement was very good. The energy of the spectroscopic transitions in the UV and in the visible region showed different correlation with redox potential and quinone substituent in the series of IIDs. This behavior was rationalized by examination of the involved molecular orbitals. The results indicated that the properties of the quinone unit, such as the redox potential, could be selectively varied by substitution.

Place, publisher, year, edition, pages
2013. Vol. 117, no 2, 894-901 p.
National Category
Physical Chemistry Engineering and Technology
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
URN: urn:nbn:se:uu:diva-192605DOI: 10.1021/jp311009zISI: 000313932800017OAI: oai:DiVA.org:uu-192605DiVA: diva2:600163
Available from: 2013-01-23 Created: 2013-01-23 Last updated: 2017-12-06Bibliographically 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, ChristofferGogoll, AdolfStrømme, MariaSjödin, Martin

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