Fluorinating π‐Extended Molecular Acceptors Yields Highly Connected Crystal Structures and Low Reorganization Energies for Efficient Solar Cells

Swick, Steven M.; Alzola, Joaquin M.; Sangwan, Vinod K.; Amsterdam, Samuel H.; Zhu, Weigang; Jones, Leighton O.; Powers‐Riggs, Natalia; Facchetti, Antonio; Kohlstedt, Kevin L.; Schatz, George C.; Hersam, Mark C.; Wasielewski, Michael R.; Marks, Tobin J.

doi:10.1002/aenm.202000635

Fluorinating π‐Extended Molecular Acceptors Yields Highly Connected Crystal Structures and Low Reorganization Energies for Efficient Solar Cells

Journal Article · Mon May 04 00:00:00 EDT 2020 · Advanced Energy Materials

DOI:https://doi.org/10.1002/aenm.202000635· OSTI ID:1617075

^[1]; Alzola, Joaquin M. ^[1]; ^[2]; Amsterdam, Samuel H. ^[1]; ^[1]; ^[1]; ^[1]; ^[3]; ^[1]; ^[1]; ^[4]; ^[1]; ^[4]

Department of Chemistry Northwestern University Evanston IL 60208 USA, Center for Light Energy Activated Redox Processes Northwestern University Evanston IL 60208 USA
Department of Materials Science and Engineering Northwestern University Evanston IL 60208 USA
Center for Light Energy Activated Redox Processes Northwestern University Evanston IL 60208 USA
Department of Chemistry Northwestern University Evanston IL 60208 USA, Center for Light Energy Activated Redox Processes Northwestern University Evanston IL 60208 USA, Department of Materials Science and Engineering Northwestern University Evanston IL 60208 USA

Abstract

The synthesis and characterization of new semiconducting materials is essential for developing high‐efficiency organic solar cells. Here, the synthesis, physiochemical properties, thin film morphology, and photovoltaic response of ITN‐F4 and ITzN‐F4, the first indacenodithienothiophene nonfullerene acceptors that combine π‐extension and fluorination, are reported. The neat acceptors and bulk‐heterojunction blend films with fluorinated donor polymer poly{[4,8‐bis[5‐(2‐ethylhexyl)‐4‐fluoro‐2‐thienyl]benzo[1,2‐b:4,5‐ b ′]‐dithiophene‐2,6‐diyl]‐ alt ‐[2,5‐thiophenediyl[5,7‐bis(2‐ethylhexyl)‐4,8‐dioxo‐4 H ,8 H ‐benzo[1,2‐ c :4,5‐ c ′]dithiophene‐1,3‐diyl]]} (PBDB‐TF, also known as PM6) are investigated using a battery of techniques, including single crystal X‐ray diffraction, fs transient absorption spectroscopy (fsTA), photovoltaic response, space‐charge‐limited current transport, impedance spectroscopy, grazing incidence wide angle X‐ray scattering, and density functional theory level computation. ITN‐F4 and ITzN‐F4 are found to provide power conversion efficiencies greater and internal reorganization energies less than their non‐π‐extended and nonfluorinated counterparts when paired with PBDB‐TF. Additionally, ITN‐F4 and ITzN‐F4 exhibit favorable bulk‐heterojunction relevant single crystal packing architectures. fsTA reveals that both ITN‐F4 and ITzN‐F4 undergo ultrafast hole transfer (<300 fs) in films with PBDB‐TF, despite excimer state formation in both the neat and blend films. Taken together and in comparison to related structures, these results demonstrate that combined fluorination and π‐extension synergistically promote crystallographic π‐face‐to‐face packing, increase crystallinity, reduce internal reorganization energies, increase interplanar π–π electronic coupling, and increase power conversion efficiency.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0001059

OSTI ID:: 1617075

Alternate ID(s):: OSTI ID: 1638723

Journal Information:: Advanced Energy Materials, Journal Name: Advanced Energy Materials Journal Issue: 23 Vol. 10; ISSN 1614-6832

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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