Linear side chains in benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c] pyrrole-4,6-dione polymers direct self-assembly and solar cell performance

Handle URI:
http://hdl.handle.net/10754/562691
Title:
Linear side chains in benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c] pyrrole-4,6-dione polymers direct self-assembly and solar cell performance
Authors:
Cabanetos, Clement; El Labban, Abdulrahman ( 0000-0001-9891-0851 ) ; Bartelt, Jonathan A.; Douglas, Jessica D.; Mateker, William R.; Frechet, Jean ( 0000-0001-6419-0163 ) ; McGehee, Michael D.; Beaujuge, Pierre
Abstract:
While varying the size and branching of solubilizing side chains in π-conjugated polymers impacts their self-assembling properties in thin-film devices, these structural changes remain difficult to anticipate. This report emphasizes the determining role that linear side-chain substituents play in poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers for bulk heterojunction (BHJ) solar cell applications. We show that replacing branched side chains by linear ones in the BDT motifs induces a critical change in polymer self-assembly and backbone orientation in thin films that correlates with a dramatic drop in solar cell efficiency. In contrast, we show that for polymers with branched alkyl-substituted BDT motifs, controlling the number of aliphatic carbons in the linear N-alkyl-substituted TPD motifs is a major contributor to improved material performance. With this approach, PBDTTPD polymers were found to reach power conversion efficiencies of 8.5% and open-circuit voltages of 0.97 V in BHJ devices with PC71BM, making PBDTTPD one of the best polymer donors for use in the high-band-gap cell of tandem solar cells. © 2013 American Chemical Society.
KAUST Department:
Solar and Photovoltaic Engineering Research Center (SPERC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division
Publisher:
American Chemical Society
Journal:
Journal of the American Chemical Society
Issue Date:
27-Mar-2013
DOI:
10.1021/ja400365b
Type:
Article
ISSN:
00027863
Sponsors:
The authors acknowledge financial support under Baseline Research Funding from KAUST. Part of this work was supported by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by KAUST. The authors thank KAUST Analytical Core Laboratories for mass spectrometry and elemental analyses and Dr. Michael Toney, Dr. Kristin Schmidt, and Dr. Christopher Tassone for their support with the GIXS experiments. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource User Facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorCabanetos, Clementen
dc.contributor.authorEl Labban, Abdulrahmanen
dc.contributor.authorBartelt, Jonathan A.en
dc.contributor.authorDouglas, Jessica D.en
dc.contributor.authorMateker, William R.en
dc.contributor.authorFrechet, Jeanen
dc.contributor.authorMcGehee, Michael D.en
dc.contributor.authorBeaujuge, Pierreen
dc.date.accessioned2015-08-03T11:01:40Zen
dc.date.available2015-08-03T11:01:40Zen
dc.date.issued2013-03-27en
dc.identifier.issn00027863en
dc.identifier.doi10.1021/ja400365ben
dc.identifier.urihttp://hdl.handle.net/10754/562691en
dc.description.abstractWhile varying the size and branching of solubilizing side chains in π-conjugated polymers impacts their self-assembling properties in thin-film devices, these structural changes remain difficult to anticipate. This report emphasizes the determining role that linear side-chain substituents play in poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymers for bulk heterojunction (BHJ) solar cell applications. We show that replacing branched side chains by linear ones in the BDT motifs induces a critical change in polymer self-assembly and backbone orientation in thin films that correlates with a dramatic drop in solar cell efficiency. In contrast, we show that for polymers with branched alkyl-substituted BDT motifs, controlling the number of aliphatic carbons in the linear N-alkyl-substituted TPD motifs is a major contributor to improved material performance. With this approach, PBDTTPD polymers were found to reach power conversion efficiencies of 8.5% and open-circuit voltages of 0.97 V in BHJ devices with PC71BM, making PBDTTPD one of the best polymer donors for use in the high-band-gap cell of tandem solar cells. © 2013 American Chemical Society.en
dc.description.sponsorshipThe authors acknowledge financial support under Baseline Research Funding from KAUST. Part of this work was supported by the Center for Advanced Molecular Photovoltaics (CAMP) (Award KUS-C1-015-21) made possible by KAUST. The authors thank KAUST Analytical Core Laboratories for mass spectrometry and elemental analyses and Dr. Michael Toney, Dr. Kristin Schmidt, and Dr. Christopher Tassone for their support with the GIXS experiments. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource User Facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.en
dc.publisherAmerican Chemical Societyen
dc.titleLinear side chains in benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c] pyrrole-4,6-dione polymers direct self-assembly and solar cell performanceen
dc.typeArticleen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalJournal of the American Chemical Societyen
dc.contributor.institutionDepartment of Materials Science and Engineering, Stanford University, Stanford, CA 94305, United Statesen
dc.contributor.institutionDepartment of Chemistry, University of California, Berkeley, CA 94720, United Statesen
kaust.authorCabanetos, Clementen
kaust.authorEl Labban, Abdulrahmanen
kaust.authorFrechet, Jeanen
kaust.authorBeaujuge, Pierreen
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