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A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
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.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för fysikalisk och analytisk kemi, Analytisk kemi.
Vise andre og tillknytning
2016 (engelsk)Inngår i: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 12, s. 2682-2688Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) (3), is prepared from glycidol in four steps in 28% overall yield. pyEDOT features an ethynyl group on its ethylenedioxy bridge, allowing further functionalization by alkyne chemistry. Its usefulness is demonstrated by a series of functionalized polythiophene derivatives that were obtained by pre- and post-electropolymerization transformations, provided by the synthetic ease of the Sonogashira coupling and click chemistry.

sted, utgiver, år, opplag, sider
2016. Vol. 12, s. 2682-2688
Emneord [en]
electropolymerization, functional polymers, polythiophene, Sonogashira coupling, thiophene
HSV kategori
Forskningsprogram
Teknisk fysik med inriktning mot nanoteknologi och funktionella material
Identifikatorer
URN: urn:nbn:se:uu:diva-310098DOI: 10.3762/bjoc.12.265ISI: 000391506600001OAI: oai:DiVA.org:uu-310098DiVA, id: diva2:1054890
Forskningsfinansiär
Swedish Research Council, VR 621-2011-4423 2015-4870Swedish Foundation for Strategic Research Swedish Energy AgencyTilgjengelig fra: 2016-12-09 Laget: 2016-12-09 Sist oppdatert: 2017-11-29bibliografisk kontrollert
Inngår i avhandling
1. Conducting Redox Polymers for Electrode Materials: Synthetic Strategies and Electrochemical Properties
Åpne denne publikasjonen i ny fane eller vindu >>Conducting Redox Polymers for Electrode Materials: Synthetic Strategies and Electrochemical Properties
2017 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

Organic electrode materials represent an intriguing alternative to their inorganic counterparts due to their sustainable and environmental-friendly properties. Their plastic character allows for the realization of light-weight, versatile and disposable devices for energy storage. Conducting redox polymers (CRPs) are one type of the organic electrode materials involved, which consist of a π-conjugated polymer backbone and covalently attached redox units, the so-called pendant. The polymer backbone can provide conductivity while it is oxidized or reduced (i. e., p- or n-doped) and the concurrent redox chemistry of the pendant provides charge capacity. The combination of these two components enables CRPs to provide both high charge capacity and high power capability. This dyad polymeric framework provides a solution to the two main problems associated with organic electrode materials based on small molecules: the dissolution of the active material in the electrolyte, and the sluggish charge transport within the material. This thesis introduces a general synthetic strategy to obtain the monomeric CRPs building blocks, followed by electrochemical polymerization to afford the active CRPs material. The choice of pendant and of polymer backbone depends on the potential match between these two components, i.e. the redox reaction of the pendant and the doping of backbone occurring within the same potential region. In the thesis, terephthalate and polythiophene were selected as the pendant and polymer backbone respectively, to get access to low potential CRPs. It was found that the presence of a non-conjugated linker between polymer backbone and pendant is essential for the polymerizability of the monomers as well as for the preservation of individual redox activities. The resulting CRPs exhibited fast charge transport within the polymer film and low activation barriers for charge propagation. These low potential CRPs were designed as the anode materials for energy storage applications. The combination of redox active pendant as charge carrier and a conductive polymer backbone reveals new insights into the requirements of organic matter based electrical energy storage materials.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2017. s. 83
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1604
Emneord
Organic electrode material, Energy storage, Conducting redox polymer, Polythiophene, Terephthalate, PEDOT
HSV kategori
Forskningsprogram
Kemi med inriktning mot organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-334562 (URN)978-91-513-0168-6 (ISBN)
Disputas
2018-01-19, B41, BMC, Husargatan, Uppsala, 09:15 (engelsk)
Opponent
Veileder
Forskningsfinansiär
SweGRIDS - Swedish Centre for Smart Grids and Energy StorageSwedish Research CouncilSwedish Foundation for Strategic Research
Tilgjengelig fra: 2017-12-21 Laget: 2017-11-23 Sist oppdatert: 2018-03-08

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