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

Title: 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 ^[1]; Jones, Leighton ^[1]; Fu, Bo ^[1]; Aldrich, Thomas J. ^[1]; Kohlstedt, Kevin L. ^[1]; Schatz, George C. ^[1]; Facchetti, Antonio ^[1];

^[1]

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.

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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, Vol. 20, Issue 20; ISSN 1439-4235

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 41 works

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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
Ultrafast Long-Range Charge Separation in Organic Semiconductor Photovoltaic Diodes Gelinas, Simon; Rao, Akshay; Kumar, Abhishek 19th International Conference on Ultrafast Phenomena https://doi.org/10.1364/up.2014.07.mon.c.7	conference	January 2014
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
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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Fluoro-alkyl substituted isothianaphthene bisimides as stable n-type semiconductors Chen, Xiaolong; Zhang, Dongwei; He, Yaowu Materials Chemistry Frontiers, Vol. 4, Issue 12 https://doi.org/10.1039/d0qm00137f	journal	January 2020

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Related Subjects

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

CCDC 1946198: Experimental Crystal Structure Determination M., Swick, Steven; Tim, Gebraad,; Leighton, Jones, https://doi.org/10.5517/ccdc.csd.cc23b5l7 The current record is supplemented by this dataset	dataset	January 2020
CCDC 1946199: Experimental Crystal Structure Determination M., Swick, Steven; Tim, Gebraad,; Leighton, Jones, https://doi.org/10.5517/ccdc.csd.cc23b5m8 The current record is supplemented by this dataset	dataset	January 2020
CCDC 1946200: Experimental Crystal Structure Determination M., Swick, Steven; Tim, Gebraad,; Leighton, Jones, https://doi.org/10.5517/ccdc.csd.cc23b5n9 The current record is supplemented by this dataset	dataset	January 2020