The Crucial Role of Fluorine in Fully Alkylated Ladder Type Carbazole Based Non-fullerene Organic Solar Cells

Qiao He; Munazza Shahid; Xuechen Jiao; Eliot Gann; Flurin Eisner; Tingmang Wu; Zhuping Fei; Thomas D. Anthopoulos; Christopher R. McNeill; Martin J. Heeney

doi:10.1021/acsami.0c00981

The Crucial Role of Fluorine in Fully Alkylated Ladder Type Carbazole Based Non-fullerene Organic Solar Cells

Qiao He, Munazza Shahid, Xuechen Jiao, Eliot Gann, Flurin Eisner, Tingmang Wu, Zhuping Fei, Thomas D. Anthopoulos, Christopher R. McNeill, Martin J. Heeney

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

Two fused ladder type non-fullerene acceptors, DTCCIC and DTCCIC-4F, based on an electron-donating alkylated dithienocyclopentacarbazole core flanked by electron-withdrawing non-fluorinated or fluorinated 1,1-dicyanomethylene-3-indanone (IC or IC-4F), are prepared and utilized in organic solar cells (OSCs). The two new molecules reveal planar structures and strong aggregation behavior, and fluorination is shown to red shift the optical band gap and down shift energy levels. OSCs based on DTCCIC-4F exhibit a power conversion efficiency of 12.6 %, much higher than that of DTCCIC based devices (6.2 %). Microstructural studies reveal that while both acceptors are highly crystalline, bulk heterojunction blends based on the non-fluorinated DTCCIC result in overly coarse domains, while blends based on the fluorinated DTCCIC-4F exhibit a more optimal nanoscale morphology. These results highlight the importance of end group fluorination in controlling molecular aggregation and miscibility.

Original language	English (US)
Pages (from-to)	9555-9562
Number of pages	8
Journal	ACS Applied Materials & Interfaces
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/acsami.0c00981
State	Published - Jan 30 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Imperial College authors thank the China Scholarship Council (CSC) via the CSC Imperial Scholarship, the Daphne Jackson Trust (supported by RSC and EPSRC), the Global Research Laboratory Program of the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (NRF-2017K1A1A2013153), and the Royal Society and Wolfson Foundation (for Royal Society Wolfson Fellowship) for funding. ZF thanks 'the National Science Foundation of China (NSFC, Project No. 21975176). TA acknowledges the King Abdullah University
of Science and Technology (KAUST) for financial support. QH acknowledges valuable discussions with Dr Cenqi Yan. This work was performed in part on the SAXS/WAXS beamline47 at the Australian Synchrotron, part of ANSTO. This research used the Spectroscopy Soft and Tender (SST-1) beamline of the National Synchrotron Light Source II, a U.S. Department of Energy (DOE) Office of Science User
Facility operated for the DOE Office of Science by Brookhaven National Laboratory under Contract No. DE-
SC0012704. CRM acknowledges travel funding provided by the International Synchrotron Access Program (ISAP) managed by the Australian Synchrotron, part of ANSTO (AS/IA192/15608), and funded by the Australian Government

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https://repository.kaust.edu.sa/bitstream/10754/661462/1/acsami.0c00981.pdf

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@article{74aa196c294349cf86bb5f60a1db98a9,

title = "The Crucial Role of Fluorine in Fully Alkylated Ladder Type Carbazole Based Non-fullerene Organic Solar Cells",

abstract = "Two fused ladder type non-fullerene acceptors, DTCCIC and DTCCIC-4F, based on an electron-donating alkylated dithienocyclopentacarbazole core flanked by electron-withdrawing non-fluorinated or fluorinated 1,1-dicyanomethylene-3-indanone (IC or IC-4F), are prepared and utilized in organic solar cells (OSCs). The two new molecules reveal planar structures and strong aggregation behavior, and fluorination is shown to red shift the optical band gap and down shift energy levels. OSCs based on DTCCIC-4F exhibit a power conversion efficiency of 12.6 %, much higher than that of DTCCIC based devices (6.2 %). Microstructural studies reveal that while both acceptors are highly crystalline, bulk heterojunction blends based on the non-fluorinated DTCCIC result in overly coarse domains, while blends based on the fluorinated DTCCIC-4F exhibit a more optimal nanoscale morphology. These results highlight the importance of end group fluorination in controlling molecular aggregation and miscibility.",

author = "Qiao He and Munazza Shahid and Xuechen Jiao and Eliot Gann and Flurin Eisner and Tingmang Wu and Zhuping Fei and Anthopoulos, {Thomas D.} and McNeill, {Christopher R.} and Heeney, {Martin J.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Imperial College authors thank the China Scholarship Council (CSC) via the CSC Imperial Scholarship, the Daphne Jackson Trust (supported by RSC and EPSRC), the Global Research Laboratory Program of the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (NRF-2017K1A1A2013153), and the Royal Society and Wolfson Foundation (for Royal Society Wolfson Fellowship) for funding. ZF thanks 'the National Science Foundation of China (NSFC, Project No. 21975176). TA acknowledges the King Abdullah University of Science and Technology (KAUST) for financial support. QH acknowledges valuable discussions with Dr Cenqi Yan. This work was performed in part on the SAXS/WAXS beamline47 at the Australian Synchrotron, part of ANSTO. This research used the Spectroscopy Soft and Tender (SST-1) beamline of the National Synchrotron Light Source II, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Brookhaven National Laboratory under Contract No. DE- SC0012704. CRM acknowledges travel funding provided by the International Synchrotron Access Program (ISAP) managed by the Australian Synchrotron, part of ANSTO (AS/IA192/15608), and funded by the Australian Government",

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AU - He, Qiao

AU - Shahid, Munazza

AU - Jiao, Xuechen

AU - Gann, Eliot

AU - Eisner, Flurin

AU - Wu, Tingmang

AU - Fei, Zhuping

AU - Anthopoulos, Thomas D.

AU - McNeill, Christopher R.

AU - Heeney, Martin J.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Imperial College authors thank the China Scholarship Council (CSC) via the CSC Imperial Scholarship, the Daphne Jackson Trust (supported by RSC and EPSRC), the Global Research Laboratory Program of the National Research Foundation (NRF) funded by the Ministry of Science, ICT & Future Planning (NRF-2017K1A1A2013153), and the Royal Society and Wolfson Foundation (for Royal Society Wolfson Fellowship) for funding. ZF thanks 'the National Science Foundation of China (NSFC, Project No. 21975176). TA acknowledges the King Abdullah University of Science and Technology (KAUST) for financial support. QH acknowledges valuable discussions with Dr Cenqi Yan. This work was performed in part on the SAXS/WAXS beamline47 at the Australian Synchrotron, part of ANSTO. This research used the Spectroscopy Soft and Tender (SST-1) beamline of the National Synchrotron Light Source II, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Brookhaven National Laboratory under Contract No. DE- SC0012704. CRM acknowledges travel funding provided by the International Synchrotron Access Program (ISAP) managed by the Australian Synchrotron, part of ANSTO (AS/IA192/15608), and funded by the Australian Government

PY - 2020/1/30

Y1 - 2020/1/30

N2 - Two fused ladder type non-fullerene acceptors, DTCCIC and DTCCIC-4F, based on an electron-donating alkylated dithienocyclopentacarbazole core flanked by electron-withdrawing non-fluorinated or fluorinated 1,1-dicyanomethylene-3-indanone (IC or IC-4F), are prepared and utilized in organic solar cells (OSCs). The two new molecules reveal planar structures and strong aggregation behavior, and fluorination is shown to red shift the optical band gap and down shift energy levels. OSCs based on DTCCIC-4F exhibit a power conversion efficiency of 12.6 %, much higher than that of DTCCIC based devices (6.2 %). Microstructural studies reveal that while both acceptors are highly crystalline, bulk heterojunction blends based on the non-fluorinated DTCCIC result in overly coarse domains, while blends based on the fluorinated DTCCIC-4F exhibit a more optimal nanoscale morphology. These results highlight the importance of end group fluorination in controlling molecular aggregation and miscibility.

AB - Two fused ladder type non-fullerene acceptors, DTCCIC and DTCCIC-4F, based on an electron-donating alkylated dithienocyclopentacarbazole core flanked by electron-withdrawing non-fluorinated or fluorinated 1,1-dicyanomethylene-3-indanone (IC or IC-4F), are prepared and utilized in organic solar cells (OSCs). The two new molecules reveal planar structures and strong aggregation behavior, and fluorination is shown to red shift the optical band gap and down shift energy levels. OSCs based on DTCCIC-4F exhibit a power conversion efficiency of 12.6 %, much higher than that of DTCCIC based devices (6.2 %). Microstructural studies reveal that while both acceptors are highly crystalline, bulk heterojunction blends based on the non-fluorinated DTCCIC result in overly coarse domains, while blends based on the fluorinated DTCCIC-4F exhibit a more optimal nanoscale morphology. These results highlight the importance of end group fluorination in controlling molecular aggregation and miscibility.

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DO - 10.1021/acsami.0c00981

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JO - ACS Applied Materials & Interfaces

JF - ACS Applied Materials & Interfaces

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ER -

The Crucial Role of Fluorine in Fully Alkylated Ladder Type Carbazole Based Non-fullerene Organic Solar Cells

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