Redox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devices

Handle URI:
http://hdl.handle.net/10754/627277
Title:
Redox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devices
Authors:
Giovannitti, Alexander ( 0000-0003-4778-3615 ) ; Thorley, Karl J.; Nielsen, Christian B.; Li, Jun; Donahue, Mary J.; Malliaras, George G.; Rivnay, Jonathan; McCulloch, Iain ( 0000-0002-6340-7217 )
Abstract:
Organic semiconductors can be employed as the active layer in accumulation mode organic electrochemical transistors (OECTs), where redox stability in aqueous electrolytes is important for long-term recordings of biological events. It is observed that alkoxy-benzo[1,2-b:4,5-b′]dithiophene (BDT) copolymers can be extremely unstable when they are oxidized in aqueous solutions. The redox stability of these copolymers can be improved by molecular design of the copolymer where it is observed that the electron rich comonomer 3,3′-dimethoxy-2,2′-bithiophene (MeOT2) lowers the oxidation potential and also stabilizes positive charges through delocalization and resonance effects. For copolymers where the comonomers do not have the same ability to stabilize positive charges, irreversible redox reactions are observed with the formation of quinone structures, being detrimental to performance of the materials in OECTs. Charge distribution along the copolymer from density functional theory calculations is seen to be an important factor in the stability of the charged copolymer. As a result of the stabilizing effect of the comonomer, a highly stable OECT performance is observed with transconductances in the mS range. The analysis of the decomposition pathway also raises questions about the general stability of the alkoxy-BDT unit, which is heavily used in donor-acceptor copolymers in the field of photovoltaics.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Solar Center (KSC)
Citation:
Giovannitti A, Thorley KJ, Nielsen CB, Li J, Donahue MJ, et al. (2018) Redox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devices. Advanced Functional Materials: 1706325. Available: http://dx.doi.org/10.1002/adfm.201706325.
Publisher:
Wiley-Blackwell
Journal:
Advanced Functional Materials
Issue Date:
23-Feb-2018
DOI:
10.1002/adfm.201706325
Type:
Article
ISSN:
1616-301X
Sponsors:
The authors thank King Abdullah University of Science and Technology, Badische Anilin and Soda Fabrik, Engineering and Physical Sciences Research Council Project EP/G037515/1, EP/M005143/1, EP/N509486/1, EC FP7 Project SC2 (610115), and EC H2020 Project SOLEDLIGHT (643791) for the financial support.
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/adfm.201706325/full
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Solar Center (KSC)

Full metadata record

DC FieldValue Language
dc.contributor.authorGiovannitti, Alexanderen
dc.contributor.authorThorley, Karl J.en
dc.contributor.authorNielsen, Christian B.en
dc.contributor.authorLi, Junen
dc.contributor.authorDonahue, Mary J.en
dc.contributor.authorMalliaras, George G.en
dc.contributor.authorRivnay, Jonathanen
dc.contributor.authorMcCulloch, Iainen
dc.date.accessioned2018-03-11T06:54:14Z-
dc.date.available2018-03-11T06:54:14Z-
dc.date.issued2018-02-23en
dc.identifier.citationGiovannitti A, Thorley KJ, Nielsen CB, Li J, Donahue MJ, et al. (2018) Redox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devices. Advanced Functional Materials: 1706325. Available: http://dx.doi.org/10.1002/adfm.201706325.en
dc.identifier.issn1616-301Xen
dc.identifier.doi10.1002/adfm.201706325en
dc.identifier.urihttp://hdl.handle.net/10754/627277-
dc.description.abstractOrganic semiconductors can be employed as the active layer in accumulation mode organic electrochemical transistors (OECTs), where redox stability in aqueous electrolytes is important for long-term recordings of biological events. It is observed that alkoxy-benzo[1,2-b:4,5-b′]dithiophene (BDT) copolymers can be extremely unstable when they are oxidized in aqueous solutions. The redox stability of these copolymers can be improved by molecular design of the copolymer where it is observed that the electron rich comonomer 3,3′-dimethoxy-2,2′-bithiophene (MeOT2) lowers the oxidation potential and also stabilizes positive charges through delocalization and resonance effects. For copolymers where the comonomers do not have the same ability to stabilize positive charges, irreversible redox reactions are observed with the formation of quinone structures, being detrimental to performance of the materials in OECTs. Charge distribution along the copolymer from density functional theory calculations is seen to be an important factor in the stability of the charged copolymer. As a result of the stabilizing effect of the comonomer, a highly stable OECT performance is observed with transconductances in the mS range. The analysis of the decomposition pathway also raises questions about the general stability of the alkoxy-BDT unit, which is heavily used in donor-acceptor copolymers in the field of photovoltaics.en
dc.description.sponsorshipThe authors thank King Abdullah University of Science and Technology, Badische Anilin and Soda Fabrik, Engineering and Physical Sciences Research Council Project EP/G037515/1, EP/M005143/1, EP/N509486/1, EC FP7 Project SC2 (610115), and EC H2020 Project SOLEDLIGHT (643791) for the financial support.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/adfm.201706325/fullen
dc.subjectOrganic bioelectronicsen
dc.subjectOrganic electrochemical transistorsen
dc.subjectOrganic semiconductorsen
dc.subjectQuinonesen
dc.subjectStabilityen
dc.titleRedox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devicesen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentKAUST Solar Center (KSC)en
dc.identifier.journalAdvanced Functional Materialsen
dc.contributor.institutionDepartment of Chemistry and Centre for Plastic Electronics Imperial College London Exhibition Road London SW7 2AZ UKen
dc.contributor.institutionMaterials Research Institute and School of Biological and Chemical Sciences Queen Mary University of London Mile End Road London E1 4NS UKen
dc.contributor.institutionDepartment of Bioelectronics École Nationale Supérieure des Mines CMP-EMSE MOC Gardanne 13541 Franceen
dc.contributor.institutionElectrical Engineering Division University of Cambridge 9 JJ Thomson Ave Cambridge CB3 0FA UKen
dc.contributor.institutionSimpson Querrey Institute Northwestern University 303 E, Superior, Suite 11-131 Chicago 60611IL USAen
dc.contributor.institutionDepartment of Biomedical Engineering Northwestern University 2145 Sheridan Road Evanston 60208-3109IL USAen
kaust.authorMcCulloch, Iainen
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