Importance of the Donor:Fullerene intermolecular arrangement for high-efficiency organic photovoltaics

Handle URI:
http://hdl.handle.net/10754/563627
Title:
Importance of the Donor:Fullerene intermolecular arrangement for high-efficiency organic photovoltaics
Authors:
Graham, Kenneth; Cabanetos, Clement; Jahnke, Justin P.; Idso, Matthew N.; El Labban, Abdulrahman ( 0000-0001-9891-0851 ) ; Ngongang Ndjawa, Guy Olivier ( 0000-0001-7400-9540 ) ; Heumueller, Thomas; Vandewal, Koen; Salleo, Alberto; Chmelka, Bradley F.; Amassian, Aram ( 0000-0002-5734-1194 ) ; Beaujuge, Pierre; McGehee, Michael D.
Abstract:
The performance of organic photovoltaic (OPV) material systems are hypothesized to depend strongly on the intermolecular arrangements at the donor:fullerene interfaces. A review of some of the most efficient polymers utilized in polymer:fullerene PV devices, combined with an analysis of reported polymer donor materials wherein the same conjugated backbone was used with varying alkyl substituents, supports this hypothesis. Specifically, the literature shows that higher-performing donor-acceptor type polymers generally have acceptor moieties that are sterically accessible for interactions with the fullerene derivative, whereas the corresponding donor moieties tend to have branched alkyl substituents that sterically hinder interactions with the fullerene. To further explore the idea that the most beneficial polymer:fullerene arrangement involves the fullerene docking with the acceptor moiety, a family of benzo[1,2-b:4,5-b]dithiophene-thieno[3,4-c]pyrrole-4,6-dione polymers (PBDTTPD derivatives) was synthesized and tested in a variety of PV device types with vastly different aggregation states of the polymer. In agreement with our hypothesis, the PBDTTPD derivative with a more sterically accessible acceptor moiety and a more sterically hindered donor moiety shows the highest performance in bulk-heterojunction, bilayer, and low-polymer concentration PV devices where fullerene derivatives serve as the electron-accepting materials. Furthermore, external quantum efficiency measurements of the charge-transfer state and solid-state two-dimensional (2D) 13C{1H} heteronuclear correlation (HETCOR) NMR analyses support that a specific polymer:fullerene arrangement is present for the highest performing PBDTTPD derivative, in which the fullerene is in closer proximity to the acceptor moiety of the polymer. This work demonstrates that the polymer:fullerene arrangement and resulting intermolecular interactions may be key factors in determining the performance of OPV material systems. © 2014 American Chemical Society.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Solar and Photovoltaic Engineering Research Center (SPERC); Materials Science and Engineering Program; Chemical Science Program; Organic Electronics and Photovoltaics Group
Publisher:
American Chemical Society (ACS)
Journal:
Journal of the American Chemical Society
Issue Date:
9-Jul-2014
DOI:
10.1021/ja502985g
Type:
Article
ISSN:
00027863
Sponsors:
This publication was supported by the Center for Advanced Molecular Photovoltaics (Award No KUS-C1-015-21) and was made possible by King Abdullah University of Science and Technology (KAUST). K.R.G. and A.A. acknowledge SABIC for a postdoctoral fellowship. G.O.N.N., K.R.G., M.D.M., and A.A. acknowledge the Office of Competitive Research Funds for a GRP-CF award. T.H. gratefully acknowledges a "DAAD Doktorantenstipendium" and the SFB 953 "Synthetic Carbon Allotropes". Use of the Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, is supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Contract No. DE-AC02-76SF00515. The NMR experiments were conducted in the Central Facilities of the UCSB Materials Research Laboratory supported by the MRSEC program of the U.S. NSF under Award No. DMR-1121053. The work at UCSB was supported by the USARO through the Institute for Collaborative Biotechnologies under Contract No. W911NF-09-D-0001. The authors also thank Dr. Chad Risko and Prof. Jean-Luc Bredas for helpful discussions.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Materials Science and Engineering Program; Solar and Photovoltaic Engineering Research Center (SPERC)

Full metadata record

DC FieldValue Language
dc.contributor.authorGraham, Kennethen
dc.contributor.authorCabanetos, Clementen
dc.contributor.authorJahnke, Justin P.en
dc.contributor.authorIdso, Matthew N.en
dc.contributor.authorEl Labban, Abdulrahmanen
dc.contributor.authorNgongang Ndjawa, Guy Olivieren
dc.contributor.authorHeumueller, Thomasen
dc.contributor.authorVandewal, Koenen
dc.contributor.authorSalleo, Albertoen
dc.contributor.authorChmelka, Bradley F.en
dc.contributor.authorAmassian, Aramen
dc.contributor.authorBeaujuge, Pierreen
dc.contributor.authorMcGehee, Michael D.en
dc.date.accessioned2015-08-03T12:04:49Zen
dc.date.available2015-08-03T12:04:49Zen
dc.date.issued2014-07-09en
dc.identifier.issn00027863en
dc.identifier.doi10.1021/ja502985gen
dc.identifier.urihttp://hdl.handle.net/10754/563627en
dc.description.abstractThe performance of organic photovoltaic (OPV) material systems are hypothesized to depend strongly on the intermolecular arrangements at the donor:fullerene interfaces. A review of some of the most efficient polymers utilized in polymer:fullerene PV devices, combined with an analysis of reported polymer donor materials wherein the same conjugated backbone was used with varying alkyl substituents, supports this hypothesis. Specifically, the literature shows that higher-performing donor-acceptor type polymers generally have acceptor moieties that are sterically accessible for interactions with the fullerene derivative, whereas the corresponding donor moieties tend to have branched alkyl substituents that sterically hinder interactions with the fullerene. To further explore the idea that the most beneficial polymer:fullerene arrangement involves the fullerene docking with the acceptor moiety, a family of benzo[1,2-b:4,5-b]dithiophene-thieno[3,4-c]pyrrole-4,6-dione polymers (PBDTTPD derivatives) was synthesized and tested in a variety of PV device types with vastly different aggregation states of the polymer. In agreement with our hypothesis, the PBDTTPD derivative with a more sterically accessible acceptor moiety and a more sterically hindered donor moiety shows the highest performance in bulk-heterojunction, bilayer, and low-polymer concentration PV devices where fullerene derivatives serve as the electron-accepting materials. Furthermore, external quantum efficiency measurements of the charge-transfer state and solid-state two-dimensional (2D) 13C{1H} heteronuclear correlation (HETCOR) NMR analyses support that a specific polymer:fullerene arrangement is present for the highest performing PBDTTPD derivative, in which the fullerene is in closer proximity to the acceptor moiety of the polymer. This work demonstrates that the polymer:fullerene arrangement and resulting intermolecular interactions may be key factors in determining the performance of OPV material systems. © 2014 American Chemical Society.en
dc.description.sponsorshipThis publication was supported by the Center for Advanced Molecular Photovoltaics (Award No KUS-C1-015-21) and was made possible by King Abdullah University of Science and Technology (KAUST). K.R.G. and A.A. acknowledge SABIC for a postdoctoral fellowship. G.O.N.N., K.R.G., M.D.M., and A.A. acknowledge the Office of Competitive Research Funds for a GRP-CF award. T.H. gratefully acknowledges a "DAAD Doktorantenstipendium" and the SFB 953 "Synthetic Carbon Allotropes". Use of the Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, is supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Contract No. DE-AC02-76SF00515. The NMR experiments were conducted in the Central Facilities of the UCSB Materials Research Laboratory supported by the MRSEC program of the U.S. NSF under Award No. DMR-1121053. The work at UCSB was supported by the USARO through the Institute for Collaborative Biotechnologies under Contract No. W911NF-09-D-0001. The authors also thank Dr. Chad Risko and Prof. Jean-Luc Bredas for helpful discussions.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleImportance of the Donor:Fullerene intermolecular arrangement for high-efficiency organic photovoltaicsen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentSolar and Photovoltaic Engineering Research Center (SPERC)en
dc.contributor.departmentMaterials Science and Engineering Programen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentOrganic Electronics and Photovoltaics Groupen
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 Chemical Engineering, University of California, Santa Barbara, CA 93106, United Statesen
kaust.authorGraham, Kennethen
kaust.authorCabanetos, Clementen
kaust.authorEl Labban, Abdulrahmanen
kaust.authorAmassian, Aramen
kaust.authorBeaujuge, Pierreen
kaust.authorNgongang Ndjawa, Guy Olivieren
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