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Probing Polymer-Pendant Interactions in the Conducting Redox Polymer Poly(pyrrol-3-ylhydroquinone)
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Nanoteknologi och funktionella material. (Nanoteknologi och Funktionella Material)
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Nanoteknologi och funktionella material.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Nanoteknologi och funktionella material.ORCID-id: 0000-0002-5496-9664
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.ORCID-id: 0000-0002-9092-261X
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2014 (Engelska)Ingår i: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 118, nr 41, s. 23499-23508Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Conducting polymers with redox active pendant groups show properties typical of both conducting polymers (i.e., capacitive charging and intrinsic conductivity) and redox polymers (i.e., electrochemical surface response at the formal potential of the pendant groups). The two components can also exert significant interaction on each other during their separate electrochemical reactions. In poly(pyrrol-3-ylhydroquinone), a polypyrrole derivative functionalized with hydroquinone units, the redox conversion of the pendant groups has a large impact on the polymer backbone. This interaction is manifested by a loss of bipolaron states during the hydroquinone oxidation, leading to a decreasing p-doping level with increasing potential, something which, to the best of our knowledge, has never been observed for a conducting polymer. Another effect is a contraction of the polymer film, and subsequent mass loss due to solvent expulsion upon hydroquinone oxidation, which counteracts the normal swelling of polypyrrole with increased potential. The conducting redox polymer under investigation has been synthesized via two routes, leading to different fractions of subunits bearing redox active hydroquinone groups. While the redox potentials are unaffected by the synthesis route, the backbone/pendant group interaction varies notably depending on the degree of quinone functionalization. This type of polymers could find use in, e.g., organic energy storage materials, since the polymer backbone both increases the electronic conductivity and prevents dissolution of the active material, as well as in actuator application, due to polymer contraction over the relatively narrow potential region where the pendant group redox chemistry occurs.

Ort, förlag, år, upplaga, sidor
2014. Vol. 118, nr 41, s. 23499-23508
Nationell ämneskategori
Fysikalisk kemi Teknik och teknologier
Forskningsämne
Teknisk fysik med inriktning mot nanoteknologi och funktionella material
Identifikatorer
URN: urn:nbn:se:uu:diva-230486DOI: 10.1021/jp506821zISI: 000343333600007OAI: oai:DiVA.org:uu-230486DiVA, id: diva2:745477
Tillgänglig från: 2014-09-10 Skapad: 2014-08-26 Senast uppdaterad: 2017-12-05Bibliografiskt granskad
Ingår i avhandling
1. Conducting Redox Polymers for Electrical Energy Storage: Backbone - Substituent Interactions in Quinone Polypyrrole Model Systems
Öppna denna publikation i ny flik eller fönster >>Conducting Redox Polymers for Electrical Energy Storage: Backbone - Substituent Interactions in Quinone Polypyrrole Model Systems
2014 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Uppsala: Acta Universitatis Upsaliensis, 2014. s. 72
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1177
Nyckelord
Organic energy storage, Hydroquinone polymers, Functionalized polypyrrole, Spectroelectrochemistry, Electrochemical quartz crystal microbalance, In situ conductivity
Nationell ämneskategori
Nanoteknik
Identifikatorer
urn:nbn:se:uu:diva-230647 (URN)978-91-554-9033-1 (ISBN)
Disputation
2014-10-30, Polhemssalen, Ångströmslaboratoriet, Lägerhyddsvägen 1, Uppsala, 13:30 (Engelska)
Opponent
Handledare
Tillgänglig från: 2014-10-03 Skapad: 2014-08-27 Senast uppdaterad: 2015-01-23Bibliografiskt granskad
2. Quinone-Pyrrole Dyad Based Polymers for Organic Batteries: From Design to Application
Öppna denna publikation i ny flik eller fönster >>Quinone-Pyrrole Dyad Based Polymers for Organic Batteries: From Design to Application
2017 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

Organic electrode materials are finding increasing use in energy storage devices due to their attractive properties that allow building of flexible and low weight devices in an environmentally friendlier manner than traditional alternatives. Among these organic electrode materials, conducting redox polymers (CRPs), consisting of conducing polymer (CP) with covalently attached redox active pendant groups (PG), have attracted our interests. This is due to the advantageous synergy between CP and PG, e.g. electronic conductivity, high stability and large charge storage capacity. In this thesis polypyrrole has been selected as CP and quinones as PGs. A series of quinone-pyrrole dyad polymers has been synthesized with a variety of quinone substituents, demonstrating the adjustability of quinone formal potentials by choice of substituents. Importantly, in this series we show that the CP-PG redox match, i.e. that the formal potential of the PG is within the conducting region of the CP, is a requirement for fast charge transfer from the electrode to the PGs. Moreover, a series of quinone-pyrrole dyad polymers with various linkers was synthesized, showing that the choice of linker has a pronounced impact on the interactions between the PG and CP. In addition, the temperature dependence of conductance during doping of the polymers reveals the charge transport mechanism. To summarize, the adjustability of the quinone formal potential as well as the fast charge transport in the bulk material ensures the applicability of the CRPs as electrode materials in organic batteries.

Ort, förlag, år, upplaga, sidor
Uppsala: Acta Universitatis Upsaliensis, 2017. s. 73
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1483
Nyckelord
Organic battery, conducting polymer, quinone, polypyrrole, spectroelectrochemistry, conductance
Nationell ämneskategori
Nanoteknik
Identifikatorer
urn:nbn:se:uu:diva-316492 (URN)978-91-554-9832-0 (ISBN)
Disputation
2017-04-21, Polhemsalen, Ångströmlaboratoriet, Lägerhyddsvägen 1, Uppsala, 09:15 (Engelska)
Opponent
Handledare
Tillgänglig från: 2017-03-30 Skapad: 2017-03-01 Senast uppdaterad: 2017-04-18

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