Building Blocks for High-Efficiency Organic Photovoltaics: Interplay of Molecular, Crystal, and Electronic Properties in Post-Fullerene ITIC Ensembles

Swick, Steven M.; Gebraad, Tim; Jones, Leighton; Fu, Bo; Aldrich, Thomas J.; Kohlstedt, Kevin L.; Schatz, George C.; Facchetti, Antonio; Marks, Tobin J.

doi:10.1002/cphc.201900793

Building Blocks for High-Efficiency Organic Photovoltaics: Interplay of Molecular, Crystal, and Electronic Properties in Post-Fullerene ITIC Ensembles

Journal Article · Wed Sep 11 00:00:00 EDT 2019 · ChemPhysChem

DOI:https://doi.org/10.1002/cphc.201900793· OSTI ID:1767532

Swick, Steven M. ^[1]; Gebraad, Tim ^[2]; Jones, Leighton ^[2]; Fu, Bo ^[2]; Aldrich, Thomas J. ^[2]; Kohlstedt, Kevin L. ^[2]; Schatz, George C. ^[2]; Facchetti, Antonio ^[2]; ^[2]

Northwestern Univ., Evanston, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Light Energy Activated Redox Processes (LEAP); OSTI
Northwestern Univ., Evanston, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Light Energy Activated Redox Processes (LEAP)

Accurate single-crystal X-ray diffraction data offer a unique opportunity to compare and contrast the atomistic details of bulk heterojunction photovoltaic small-molecule acceptor structure and packing, as well as provide an essential starting point for computational electronic structure and charge transport analysis. Herein, we report diffraction-derived crystal structures and computational analyses on the n-type semiconductors which enable some of the highest efficiency organic solar cells produced to date, 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene (ITIC) and seven derivatives (including three new crystal structures: 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-propylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene (ITIC-C3), 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(3-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene (m-ITIC-C6), and 3,9-bis(2-methylene-((3-(1,1-dicyanomethylene)-6,7-difluoro)-indanone))-5,5,11,11-tetrakis(4-butylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene (ITIC-C4-4F). IDTT acceptors typically pack in a face-to-face fashion with π–π distances ranging from 3.28–3.95 Å. Additionally, edge-to-face packing is observed with S...π interactions as short as 3.21–3.24 Å. Moreover, ITIC end group identities and side chain substituents influence the nature and strength of noncovalent interactions (e.g. H-bonding, π–π) and thus correlate with the observed packing motif, electronic structure, and charge transport properties of the crystals. Furthermore, density functional theory (DFT) calculations reveal relatively large nearest-neighbor intermolecular π-π electronic couplings (5.85–56.8 meV) and correlate the nature of the band structure with the dispersion interactions in the single crystals and core–end group polarization effects. Overall, this combined experimental and theoretical work reveals key insights into crystal engineering strategies for indacenodithienothiophene (IDTT) acceptors, as well as general design rules for high-efficiency post-fullerene small molecule acceptors.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Light Energy Activated Redox Processes (LEAP)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001059

OSTI ID:: 1767532

Alternate ID(s):: OSTI ID: 1571304

Journal Information:: ChemPhysChem, Journal Name: ChemPhysChem Journal Issue: 20 Vol. 20; ISSN 1439-4235

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Single-Junction Binary-Blend Nonfullerene Polymer Solar Cells with 12.1% Efficiency Fuwen, Zhao,; Li, Jiang,; Shuixing, Dai, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/2de3-a253	text	January 2017
Delineation of Thermodynamic and Kinetic Factors that Control Stability in Non-fullerene Organic Solar Cells S. J., Stuard,; J. H., Carpenter,; H., Hu, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/kn59-0e59	text	January 2019
Organic solar cells based on non-fullerene acceptors. Hou, Jianhui; Inganäs, Olle; Friend, Richard Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.22015	text	January 2018
Organic solar cells based on non-fullerene acceptors. Hou, Jianhui; Inganäs, Olle; Friend, Richard Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.47720	text	January 2018

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
bio-inspired
catalysis (heterogeneous)
catalysis (homogeneous)
charge transport
crystal structure
density functional calculations
hydrogen and fuel cells
magnetism and spin physics
materials and chemistry by design
mesostructured materials
molecular modelling
non-fullerene
optics
phonons
photosynthesis (natural and artificial)
solar (fuels)
solar (photovoltaic)
solar cells
synthesis (novel materials)
synthesis (scalable processing)
synthesis (self-assembly)

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