Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics

Handle URI:
http://hdl.handle.net/10754/562190
Title:
Functionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics
Authors:
Douglas, Jessica D.; Griffini, Gianmarco; Holcombe, Thomas W.; Young, Eric P.; Lee, Olivia P.; Chen, Mark S.; Frechet, Jean ( 0000-0001-6419-0163 )
Abstract:
A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.
KAUST Department:
Chemical Science Program; Physical Sciences and Engineering (PSE) Division
Publisher:
American Chemical Society (ACS)
Journal:
Macromolecules
Issue Date:
22-May-2012
DOI:
10.1021/ma300589k
Type:
Article
ISSN:
00249297
Sponsors:
This work was supported in part by the Director, Office of Science, Office of Basic Energy Sciences, Material Sciences and Engineering Division, of the U.S. Department of Energy under Contract DE-AC02-05CH11231 and the Frechet "Various Donors" gift fund for the support of research in new materials. G.G. thanks Fondazione Banca del Monte di Lombardia, T.W.H. thanks the National Science Foundation, and M.S.C. thanks the Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry for fellowships. The authors also thank Professors Robert Bergman and Peter Vollhardt for helpful discussions.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program

Full metadata record

DC FieldValue Language
dc.contributor.authorDouglas, Jessica D.en
dc.contributor.authorGriffini, Gianmarcoen
dc.contributor.authorHolcombe, Thomas W.en
dc.contributor.authorYoung, Eric P.en
dc.contributor.authorLee, Olivia P.en
dc.contributor.authorChen, Mark S.en
dc.contributor.authorFrechet, Jeanen
dc.date.accessioned2015-08-03T09:46:53Zen
dc.date.available2015-08-03T09:46:53Zen
dc.date.issued2012-05-22en
dc.identifier.issn00249297en
dc.identifier.doi10.1021/ma300589ken
dc.identifier.urihttp://hdl.handle.net/10754/562190en
dc.description.abstractA series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C 61-butyric acid methyl ester (PC 61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT). © 2012 American Chemical Society.en
dc.description.sponsorshipThis work was supported in part by the Director, Office of Science, Office of Basic Energy Sciences, Material Sciences and Engineering Division, of the U.S. Department of Energy under Contract DE-AC02-05CH11231 and the Frechet "Various Donors" gift fund for the support of research in new materials. G.G. thanks Fondazione Banca del Monte di Lombardia, T.W.H. thanks the National Science Foundation, and M.S.C. thanks the Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry for fellowships. The authors also thank Professors Robert Bergman and Peter Vollhardt for helpful discussions.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleFunctionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaicsen
dc.typeArticleen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalMacromoleculesen
dc.contributor.institutionDepartment of Chemistry, University of California, Berkeley, CA 94720-1460, United Statesen
dc.contributor.institutionMaterials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United Statesen
dc.contributor.institutionDepartment of Chemical Engineering, University of California, Berkeley, CA 94720-1460, United Statesen
kaust.authorFrechet, Jeanen
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.