uu.seUppsala University Publications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Synthesis and Characterization of Poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole: investigation on Backbone/Pendant Interactions in a Conducting Redox Polymer
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. (Nanoteknologi och Funktionella Material)
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials. (Nanoteknologi och Funktionella Material)ORCID iD: 0000-0003-2883-2696
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, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0002-9092-261X
Show others and affiliations
2017 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 19, no 16, 10427-10435 p.Article in journal (Refereed) Published
Abstract [en]

We herein report the synthesis and electrochemical characterization of poly-3-((2,5-hydroquinone)vinyl)-1H-pyrrole, consisting of a polypyrrole backbone derivatized at the beta position by a vinyl-hydroquinone pendant group. The structure of the polymer was characterized by solid state NMR spectroscopy. The interactions between the polypyrrole backbone and the oxidized quinone or reduced hydroquinone pendant groups are probed by several in situ methods. In situ attenuated total reflectance-Fourier transform infrared spectroscopy shows spectroscopic response from both the doping of the polymer backbone and the redox activity of the pendant groups. Using an in situ Electrochemical Quartz Crystal Microbalance we reveal that the polymer doping is unaffected by the pendant group redox chemistry, as opposed to previous reports. Despite the continuous doping the electrochemical conversion from the hydroquinone state to the quinone state results in a significant conductance drop, as observed by in situ conductivity measurements using an InterDigitated Array electrode set-up. Twisting of the conducting polymer backbone as a result of a decreased separation between pendant groups due to π-π stacking in the oxidized state is suggested as the cause of this conductance drop.

Place, publisher, year, edition, pages
2017. Vol. 19, no 16, 10427-10435 p.
National Category
Nano Technology
Identifiers
URN: urn:nbn:se:uu:diva-316490DOI: 10.1039/c6cp08736aISI: 000400117700025PubMedID: 28379225OAI: oai:DiVA.org:uu-316490DiVA: diva2:1077952
Funder
Swedish Foundation for Strategic Research Swedish Research CouncilCarl Tryggers foundation Stiftelsen Olle Engkvist ByggmästareSwedish Energy AgencyEU, Horizon 2020, 644631
Available from: 2017-03-01 Created: 2017-03-01 Last updated: 2017-05-29Bibliographically approved
In thesis
1. Quinone-Pyrrole Dyad Based Polymers for Organic Batteries: From Design to Application
Open this publication in new window or tab >>Quinone-Pyrrole Dyad Based Polymers for Organic Batteries: From Design to Application
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2017. 73 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1483
Keyword
Organic battery, conducting polymer, quinone, polypyrrole, spectroelectrochemistry, conductance
National Category
Nano Technology
Identifiers
urn:nbn:se:uu:diva-316492 (URN)978-91-554-9832-0 (ISBN)
Public defence
2017-04-21, Polhemsalen, Ångströmlaboratoriet, Lägerhyddsvägen 1, Uppsala, 09:15 (English)
Opponent
Supervisors
Available from: 2017-03-30 Created: 2017-03-01 Last updated: 2017-04-18

Open Access in DiVA

No full text

Other links

Publisher's full textPubMed

Search in DiVA

By author/editor
Hao, HuangKarlsson, ChristofferStrømme, MariaGogoll, AdolfSjödin, Martin
By organisation
Nanotechnology and Functional MaterialsOrganic Chemistry
In the same journal
Physical Chemistry, Chemical Physics - PCCP
Nano Technology

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 6740 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf