Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores

Handle URI:
http://hdl.handle.net/10754/625759
Title:
Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores
Authors:
Zhang, Siyuan; Zhang, Junxiang; Abdelsamie, Maged ( 0000-0002-4631-5409 ) ; Shi, Qinqin; Zhang, Yadong; Parker, Timothy C. ( 0000-0002-0270-0364 ) ; Jucov, Evgheni V.; Timofeeva, Tatiana V. ( 0000-0001-7475-3206 ) ; Amassian, Aram ( 0000-0002-5734-1194 ) ; Bazan, Guillermo C. ( 0000-0002-2537-0310 ) ; Blakey, Simon B. ( 0000-0002-4100-8610 ) ; Barlow, Stephen ( 0000-0001-9059-9974 ) ; Marder, Seth R. ( 0000-0001-6921-2536 )
Abstract:
Two intermediate-sized donor molecules, BBTz-X and BDT-X, have been synthesized by the Stille coupling between 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b′]dithiophen-2-yl)-7-(5′-hexyl-[2,2′-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine and either 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-2,6-diiodobenzo[1,2-d:4,5-d′]bis(thiazole) or 2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene, respectively. Both oxidation and reduction potentials for BBTz-X are anodically shifted relative to those for BDT-X, but the oxidation potential is more sensitive to the identity of the core; this is consistent with what is seen for DFT-calculated HOMO and LUMO energies and with a slightly blue-shifted absorption maximum for BBTz-X. Although DFT calculations, along with crystal structures of related compounds, suggest more planar molecular structures for BBTz-X than for BDT-X, film structures and the effects of various annealing processes on these films, as revealed by GIWAXS, are similar. The performance of BDT-X:PC61BM bulk-heterojunction solar cells is more sensitive to annealing conditions than that of BBTz-X:PC61BM cells, but under appropriate conditions, both yield power conversion efficiencies of >7%.
KAUST Department:
KAUST Solar Center (KSC); Physical Sciences and Engineering (PSE) Division
Citation:
Zhang S, Zhang J, Abdelsamie M, Shi Q, Zhang Y, et al. (2017) Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores. Chemistry of Materials 29: 7880–7887. Available: http://dx.doi.org/10.1021/acs.chemmater.7b02665.
Publisher:
American Chemical Society (ACS)
Journal:
Chemistry of Materials
Issue Date:
5-Sep-2017
DOI:
10.1021/acs.chemmater.7b02665
Type:
Article
ISSN:
0897-4756; 1520-5002
Sponsors:
The research was partly supported by the National Science Foundation, through the CCI Center for Selective C–H Functionalization (CHE-1205646 and CHE-1700982) and through the PREM program (DMR-1523611), and by the Department of the Navy, Office of Naval Research, through Award No. N00014-14-1-0580 (CAOP MURI).
Additional Links:
http://pubs.acs.org/doi/full/10.1021/acs.chemmater.7b02665
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, Siyuanen
dc.contributor.authorZhang, Junxiangen
dc.contributor.authorAbdelsamie, Mageden
dc.contributor.authorShi, Qinqinen
dc.contributor.authorZhang, Yadongen
dc.contributor.authorParker, Timothy C.en
dc.contributor.authorJucov, Evgheni V.en
dc.contributor.authorTimofeeva, Tatiana V.en
dc.contributor.authorAmassian, Aramen
dc.contributor.authorBazan, Guillermo C.en
dc.contributor.authorBlakey, Simon B.en
dc.contributor.authorBarlow, Stephenen
dc.contributor.authorMarder, Seth R.en
dc.date.accessioned2017-10-03T12:49:38Z-
dc.date.available2017-10-03T12:49:38Z-
dc.date.issued2017-09-05en
dc.identifier.citationZhang S, Zhang J, Abdelsamie M, Shi Q, Zhang Y, et al. (2017) Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores. Chemistry of Materials 29: 7880–7887. Available: http://dx.doi.org/10.1021/acs.chemmater.7b02665.en
dc.identifier.issn0897-4756en
dc.identifier.issn1520-5002en
dc.identifier.doi10.1021/acs.chemmater.7b02665en
dc.identifier.urihttp://hdl.handle.net/10754/625759-
dc.description.abstractTwo intermediate-sized donor molecules, BBTz-X and BDT-X, have been synthesized by the Stille coupling between 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b′]dithiophen-2-yl)-7-(5′-hexyl-[2,2′-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine and either 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-2,6-diiodobenzo[1,2-d:4,5-d′]bis(thiazole) or 2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene, respectively. Both oxidation and reduction potentials for BBTz-X are anodically shifted relative to those for BDT-X, but the oxidation potential is more sensitive to the identity of the core; this is consistent with what is seen for DFT-calculated HOMO and LUMO energies and with a slightly blue-shifted absorption maximum for BBTz-X. Although DFT calculations, along with crystal structures of related compounds, suggest more planar molecular structures for BBTz-X than for BDT-X, film structures and the effects of various annealing processes on these films, as revealed by GIWAXS, are similar. The performance of BDT-X:PC61BM bulk-heterojunction solar cells is more sensitive to annealing conditions than that of BBTz-X:PC61BM cells, but under appropriate conditions, both yield power conversion efficiencies of >7%.en
dc.description.sponsorshipThe research was partly supported by the National Science Foundation, through the CCI Center for Selective C–H Functionalization (CHE-1205646 and CHE-1700982) and through the PREM program (DMR-1523611), and by the Department of the Navy, Office of Naval Research, through Award No. N00014-14-1-0580 (CAOP MURI).en
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttp://pubs.acs.org/doi/full/10.1021/acs.chemmater.7b02665en
dc.titleIntermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Coresen
dc.typeArticleen
dc.contributor.departmentKAUST Solar Center (KSC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalChemistry of Materialsen
dc.contributor.institutionCenter for Organic Photonics and Electronics and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, United Statesen
dc.contributor.institutionDepartment of Chemistry, Emory University, Atlanta, Georgia 30322, United Statesen
dc.contributor.institutionDepartment of Chemistry, New Mexico Highlands University, Las Vegas, New Mexico 87701, United Statesen
dc.contributor.institutionCenter for Polymers and Organic Solids, Department of Chemistry and Biochemistry, and Department of Physics, University of California, Santa Barbara, California 93106, United Statesen
kaust.authorAbdelsamie, Mageden
kaust.authorAmassian, Aramen
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