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dc.contributor.authorDouglas, Jessica D.
dc.contributor.authorGriffini, Gianmarco
dc.contributor.authorHolcombe, Thomas W.
dc.contributor.authorYoung, Eric P.
dc.contributor.authorLee, Olivia P.
dc.contributor.authorChen, Mark S.
dc.contributor.authorFrechet, Jean
dc.date.accessioned2015-08-03T09:46:53Z
dc.date.available2015-08-03T09:46:53Z
dc.date.issued2012-05-03
dc.identifier.citationDouglas, J. D., Griffini, G., Holcombe, T. W., Young, E. P., Lee, O. P., Chen, M. S., & Fréchet, J. M. J. (2012). Functionalized Isothianaphthene Monomers That Promote Quinoidal Character in Donor–Acceptor Copolymers for Organic Photovoltaics. Macromolecules, 45(10), 4069–4074. doi:10.1021/ma300589k
dc.identifier.issn00249297
dc.identifier.doi10.1021/ma300589k
dc.identifier.urihttp://hdl.handle.net/10754/562190
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.
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.
dc.publisherAmerican Chemical Society (ACS)
dc.titleFunctionalized isothianaphthene monomers that promote quinoidal character in donor-acceptor copolymers for organic photovoltaics
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentOffice of the VP
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalMacromolecules
dc.contributor.institutionDepartment of Chemistry, University of California, Berkeley, CA 94720-1460, United States
dc.contributor.institutionMaterials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States
dc.contributor.institutionDepartment of Chemical Engineering, University of California, Berkeley, CA 94720-1460, United States
kaust.personFrechet, Jean
dc.date.published-online2012-05-03
dc.date.published-print2012-05-22


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