Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units

Handle URI:
http://hdl.handle.net/10754/622756
Title:
Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units
Authors:
Zhang, Lei; Rose, Bradley Daniel ( 0000-0002-1774-3981 ) ; Liu, Yao; Nahid, Masrur M.; Gann, Eliot; Ly, Jack; Zhao, Wei; Rosa, Stephen J.; Russell, Thomas P.; Facchetti, Antonio; McNei, Christopher R.; Bredas, Jean-Luc ( 0000-0001-7278-4471 ) ; Briseno, Alejandro L.
Abstract:
We demonstrate a new method to reverse the polarity and charge transport behavior of naphthalenediimide (NDI)-based copolymers by inserting a vinylene linker between the donor and acceptor units. The vinylene linkers minimize the intrinsic steric congestion between the NDI and thiophene moieties to prompt backbone planarity. The polymers with vinylene linkers exhibit electron n-channel transport characteristics under vacuum, similar to the benchmark polymer, P(NDI2OD-T2). To our surprise, when the polymers are measured in air, the dominant carrier type switches from n- to p-type and yield hole mobilities up to 0.45 cm(2) s(-1) with hole to electron mobility ratio of three (mu(h)/mu(e), similar to 3), which indicates that the hole density in the active layer can be significantly increased by exposure to air. This increase is consistent with the intrinsic more delocalized nature of the highest occupied molecular orbital of the charged vinylene polymer, as estimated by density functional theory (DFT) calculations, which facilitates hole transport within the polymer chains. This is the first demonstration of an efficient NDI-based hole semiconducting polymer, which will enable new developments in all-polymer solar cells, complementary circuits, and dopable polymers for use in thermoelectrics.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Solar and Photovoltaic Engineering Research Center (SPERC)
Citation:
Zhang L, Rose BD, Liu Y, Nahid MM, Gann E, et al. (2016) Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units. Chemistry of Materials 28: 8580–8590. Available: http://dx.doi.org/10.1021/acs.chemmater.6b03379.
Publisher:
American Chemical Society (ACS)
Journal:
Chemistry of Materials
Issue Date:
4-Nov-2016
DOI:
10.1021/acs.chemmater.6b03379
Type:
Article
ISSN:
0897-4756; 1520-5002
Sponsors:
L.Z., J. L., S.J.R., and A.L.B thank the Office of Naval Research (N0001471410053) and the National Science Foundation (DMR-1508627) for support of this work; Y.L. and T.P.R. acknowledge the support of the Office of Naval Research under contract N00014-15-1-2244; C.M. acknowledges funding from the Australian Research Council (FT10010075, DP130102616); B.D.R. and J.L.B. acknowledge the support from ONR-Global, Award N62909-15-1-2003, and from competitive research funding of King Abdullah University of Science and Technology. Parts of this research were undertaken on the soft X-ray and SAXS/WAXS beamlines of the Australian Synchrotron. L.Z. thanks the Fundamental Research Funds for the Central Universities (ZY1636).
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.chemmater.6b03379
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorZhang, Leien
dc.contributor.authorRose, Bradley Danielen
dc.contributor.authorLiu, Yaoen
dc.contributor.authorNahid, Masrur M.en
dc.contributor.authorGann, Elioten
dc.contributor.authorLy, Jacken
dc.contributor.authorZhao, Weien
dc.contributor.authorRosa, Stephen J.en
dc.contributor.authorRussell, Thomas P.en
dc.contributor.authorFacchetti, Antonioen
dc.contributor.authorMcNei, Christopher R.en
dc.contributor.authorBredas, Jean-Lucen
dc.contributor.authorBriseno, Alejandro L.en
dc.date.accessioned2017-01-29T13:51:36Z-
dc.date.available2017-01-29T13:51:36Z-
dc.date.issued2016-11-04en
dc.identifier.citationZhang L, Rose BD, Liu Y, Nahid MM, Gann E, et al. (2016) Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units. Chemistry of Materials 28: 8580–8590. Available: http://dx.doi.org/10.1021/acs.chemmater.6b03379.en
dc.identifier.issn0897-4756en
dc.identifier.issn1520-5002en
dc.identifier.doi10.1021/acs.chemmater.6b03379en
dc.identifier.urihttp://hdl.handle.net/10754/622756-
dc.description.abstractWe demonstrate a new method to reverse the polarity and charge transport behavior of naphthalenediimide (NDI)-based copolymers by inserting a vinylene linker between the donor and acceptor units. The vinylene linkers minimize the intrinsic steric congestion between the NDI and thiophene moieties to prompt backbone planarity. The polymers with vinylene linkers exhibit electron n-channel transport characteristics under vacuum, similar to the benchmark polymer, P(NDI2OD-T2). To our surprise, when the polymers are measured in air, the dominant carrier type switches from n- to p-type and yield hole mobilities up to 0.45 cm(2) s(-1) with hole to electron mobility ratio of three (mu(h)/mu(e), similar to 3), which indicates that the hole density in the active layer can be significantly increased by exposure to air. This increase is consistent with the intrinsic more delocalized nature of the highest occupied molecular orbital of the charged vinylene polymer, as estimated by density functional theory (DFT) calculations, which facilitates hole transport within the polymer chains. This is the first demonstration of an efficient NDI-based hole semiconducting polymer, which will enable new developments in all-polymer solar cells, complementary circuits, and dopable polymers for use in thermoelectrics.en
dc.description.sponsorshipL.Z., J. L., S.J.R., and A.L.B thank the Office of Naval Research (N0001471410053) and the National Science Foundation (DMR-1508627) for support of this work; Y.L. and T.P.R. acknowledge the support of the Office of Naval Research under contract N00014-15-1-2244; C.M. acknowledges funding from the Australian Research Council (FT10010075, DP130102616); B.D.R. and J.L.B. acknowledge the support from ONR-Global, Award N62909-15-1-2003, and from competitive research funding of King Abdullah University of Science and Technology. Parts of this research were undertaken on the soft X-ray and SAXS/WAXS beamlines of the Australian Synchrotron. L.Z. thanks the Fundamental Research Funds for the Central Universities (ZY1636).en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.chemmater.6b03379en
dc.titleEfficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Unitsen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.identifier.journalChemistry of Materialsen
dc.contributor.institutionCollege of Energy, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of Chinaen
dc.contributor.institutionDepartment of Polymer Science and Engineering, University of Massachusetts, 120 Governors Drive, Amherst, Massachusetts 01003, United Statesen
dc.contributor.institutionDepartment of Materials Science and Engineering, Monash University, Clayton, Victoria 3800, Australiaen
dc.contributor.institutionAustralian Synchrotron, 800 Blackburn Road, Clayton, Victoria 3168, Australiaen
dc.contributor.institutionPolyera Corporation, 8045 Lamon Avenue, Skokie, Illinois 60077, United Statesen
kaust.authorRose, Bradley Danielen
kaust.authorBredas, Jean-Lucen
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