Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials

Handle URI:
http://hdl.handle.net/10754/575921
Title:
Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials
Authors:
Mateker, William R.; Heumueller, Thomas; Cheacharoen, Rongrong; Sachs-Quintana, I. T.; Warnan, Julien; Liu, Xiaofeng; Bazan, Guillermo C.; Beaujuge, Pierre; McGehee, Michael D.
Abstract:
For long-term performance chemically robust materials are desired for organic solar cells (OSCs). Illuminating neat films of OSC materials in air and tracking the rate of absorption loss, or photobleaching, can quickly screen a material’s photo-chemical stability. In this report, we photobleach neat films of OSC materials including polymers, solution-processed oligomers, solution-processed small molecules, and vacuum-deposited small molecules. Across the materials we test, we observe photobleaching rates that span seven orders of magnitude. Furthermore, we find that the film morphology of any particular material impacts the observed photobleaching rate, and that amorphous films photobleach faster than crystalline ones. In an extreme case, films of amorphous rubrene photobleach at a rate 2500 times faster than polycrystalline films. When we compare density to photobleaching rate, we find that stability increases with density. We also investigate the relationship between backbone planarity and chemical reactivity. The polymer PBDTTPD is more photostable than it’s more twisted and less ordered furan derivitative, PBDFTPD. Finally, we relate our work to what is known about the chemical stability of structural polymers, organic pigments, and organic light emitting diode materials. For the highest chemical stability, planar materials that form dense, crystalline film morphologies should be designed for OSCs.
KAUST Department:
Physical Sciences and Engineering (PSE) Division
Citation:
Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials 2015:150819120334006 Chemistry of Materials
Publisher:
American Chemical Society (ACS)
Journal:
Chemistry of Materials
Issue Date:
19-Aug-2015
DOI:
10.1021/acs.chemmater.5b02341
Type:
Article
ISSN:
0897-4756; 1520-5002
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/acs.chemmater.5b02341
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorMateker, William R.en
dc.contributor.authorHeumueller, Thomasen
dc.contributor.authorCheacharoen, Rongrongen
dc.contributor.authorSachs-Quintana, I. T.en
dc.contributor.authorWarnan, Julienen
dc.contributor.authorLiu, Xiaofengen
dc.contributor.authorBazan, Guillermo C.en
dc.contributor.authorBeaujuge, Pierreen
dc.contributor.authorMcGehee, Michael D.en
dc.date.accessioned2015-08-25T08:05:25Zen
dc.date.available2015-08-25T08:05:25Zen
dc.date.issued2015-08-19en
dc.identifier.citationMolecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials 2015:150819120334006 Chemistry of Materialsen
dc.identifier.issn0897-4756en
dc.identifier.issn1520-5002en
dc.identifier.doi10.1021/acs.chemmater.5b02341en
dc.identifier.urihttp://hdl.handle.net/10754/575921en
dc.description.abstractFor long-term performance chemically robust materials are desired for organic solar cells (OSCs). Illuminating neat films of OSC materials in air and tracking the rate of absorption loss, or photobleaching, can quickly screen a material’s photo-chemical stability. In this report, we photobleach neat films of OSC materials including polymers, solution-processed oligomers, solution-processed small molecules, and vacuum-deposited small molecules. Across the materials we test, we observe photobleaching rates that span seven orders of magnitude. Furthermore, we find that the film morphology of any particular material impacts the observed photobleaching rate, and that amorphous films photobleach faster than crystalline ones. In an extreme case, films of amorphous rubrene photobleach at a rate 2500 times faster than polycrystalline films. When we compare density to photobleaching rate, we find that stability increases with density. We also investigate the relationship between backbone planarity and chemical reactivity. The polymer PBDTTPD is more photostable than it’s more twisted and less ordered furan derivitative, PBDFTPD. Finally, we relate our work to what is known about the chemical stability of structural polymers, organic pigments, and organic light emitting diode materials. For the highest chemical stability, planar materials that form dense, crystalline film morphologies should be designed for OSCs.en
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.chemmater.5b02341en
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Chemistry of Materials, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.chemmater.5b02341.en
dc.titleMolecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materialsen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalChemistry of Materialsen
dc.eprint.versionPost-printen
dc.contributor.institutionDepartment of Materials Science and Engineering, Stanford University, Stanford, CA 94305, USAen
dc.contributor.institutionCenter for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106, USAen
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)en
kaust.authorWarnan, Julienen
kaust.authorBeaujuge, Pierreen
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