Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

Zhou, Nanjia; Guo, Xugang; Ortiz, Rocio Ponce; Harschneck, Tobias; Manley, Eric F.; Lou, Sylvia J.; Hartnett, Patrick E.; Yu, Xinge; Horwitz, Noah E.; Burrezo, Paula Mayorga; Aldrich, Thomas J.; López Navarrete, Juan T.; Wasielewski, Michael R.; Chen, Lin X.; Chang, Robert. P.  H.; Facchetti, Antonio; Marks, Tobin J.

doi:10.1021/jacs.5b06462

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

Journal Article · Tue Sep 08 00:00:00 EDT 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b06462· OSTI ID:1386284

Zhou, Nanjia ^[1]; Guo, Xugang ^[2]; Ortiz, Rocio Ponce ^[3]; Harschneck, Tobias ^[1]; Manley, Eric F. ^[4]; Lou, Sylvia J. ^[1]; Hartnett, Patrick E. ^[1]; Yu, Xinge ^[1]; Horwitz, Noah E. ^[1]; Burrezo, Paula Mayorga ^[5]; Aldrich, Thomas J. ^[1]; López Navarrete, Juan T. ^[5]; Wasielewski, Michael R. ^[1]; Chen, Lin X. ^[4]; Chang, Robert. P. H. ^[1]; Facchetti, Antonio ^[6]; Marks, Tobin J. ^[1]

Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States)
Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States); South Univ. of Science and Technology of China, Guangdong (China)
Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, Málaga 29071, Spain
Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, Málaga 29071, Spain
Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States); Polyera Corporation, Skokie, IL (United States)

As effective building blocks for high-mobility transistor polymers, oligothiophenes are receiving attention for polymer solar cells (PSCs) because the resulting polymers can effectively suppress charge recombination. In this work we investigate two series of in-chain donor–acceptor copolymers, PTPDnT and PBTInT, based on thieno[3,4-c]pyrrole-4,6-dione (TPD) or bithiopheneimide (BTI) as electron acceptor units, respectively, and oligothiophenes (nTs) as donor counits, for high-performance PSCs. Intramolecular S···O interaction leads to more planar TPD polymer backbones, however backbone torsion yields greater open-circuit voltages for BTI polymers. Thiophene addition progressively raises polymer HOMOs but marginally affects their band gaps. FT-Raman spectra indicate that PTPDnT and PBTInT conjugation lengths scale with nT catenation up to $$n$$ = 3 and then saturate for longer oligomer. Furthermore, the effects of oligothiophene alkylation position are explored, revealing that the alkylation pattern greatly affects film morphology and PSC performance. The 3T with “outward” alkylation in PTPD3T and PBTI3T affords optimal $$π$$-conjugation, close stacking, long-range order, and high hole mobilities (0.1 cm²/(V s)). These characteristics contribute to the exceptional ~80% fill factors for PTPD3T-based PSCs with PCE = 7.7%. The results demonstrate that 3T is the optimal donor unit among nTs ($$n$$ = 1–4) for photovoltaic polymers. Grazing incidence wide-angle X-ray scattering, transmission electron microscopy, and time-resolved microwave conductivity measurements reveal that the terthiophene-based PTPD3T blend maintains high crystallinity with appreciable local mobility and long charge carrier lifetime. These results provide fundamental materials structure-device performance correlations and suggest guidelines for designing oligothiophene-based polymers with optimal thiophene catenation and appropriate alkylation pattern to maximize PSC performance.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)

Sponsoring Organization:: Basic Research Funds; Ministry of Economy and Competitiveness (MINECO); National Science Foundation (NSF); Peacock Team Project; Polyera Corp.; US Air Force Office of Scientific Research (AFOSR); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357; SC0001059

OSTI ID:: 1386284

Alternate ID(s):: OSTI ID: 1245962

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 39 Vol. 137; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

Journal Article · Tue Sep 08 00:00:00 EDT 2015 · Journal of the American Chemical Society · OSTI ID:1245962

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alcohols
bio-inspired
catalysis (heterogeneous)
catalysis (homogeneous)
charge transport
defects
electrodes - solar
hydrogen and fuel cells
materials and chemistry by design
membrane
optics
photosynthesis (natural and artificial)
polymer films
polymers
solar (fuels)
solar (photovoltaic)
spin dynamics
synthesis (novel materials)
synthesis (self-assembly)
thermoresponsive polymers
thiophenes

Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4-c]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers

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