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Title: Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells

Abstract

The ortho-position functionalized perylene diimide derivatives (αPPID, αPBDT) were synthesized and used as the electron acceptors in nonfullerene organic photovoltaics. Due to the good planarity of ortho-position functionalized PDI, the αPPID and αPBDT show strong tendency to form aggregate because of their enhanced intermolecular pie-pie interaction. Moreover, they maintain the pure domains and the same packing order as in the pure film if they are blended with PBT7-TH and the SCLC measurement also shows the high electron mobility. The inverted OPVs employing αPDI-based compounds as acceptor and PBT7-TH as the donor give the highest PCE of 4.92 % for αPBDT based device and 3.61 % for αPPID based device, which is 39 % and 4 % higher than that for their counterpart βPBDT and βPPID. The charge separation study shows the more efficient exciton dissociation at interfaces between PDI based compounds and PBT7-TH. In conclusion, the results suggest that compared to beta-substituted ones, alpha-substituted PDI derivatives are more promising electron acceptors for OPV.

Authors:
 [1];  [1];  [1];  [1];  [2];  [1];  [1]
+ Show Author Affiliations
  1. Univ. of Chicago, IL (United States). James Franck Inst., Dept. of Chemistry
  2. Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division; Univ. of Chicago, IL (United States). Inst. for Molecular Engineering
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); National Institute of Standards and Technology (NIST)
OSTI Identifier:
1245464
Grant/Contract Number:  
AC02-06CH11357; SC0001059; DMR-1263006; KC020301
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry of Materials
Additional Journal Information:
Journal Volume: 28; Journal Issue: 4; Journal ID: ISSN 0897-4756
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 14 SOLAR ENERGY

Citation Formats

Zhao, Donglin, Wu, Qinghe, Cai, Zhengxu, Zheng, Tianyue, Chen, Wei, Lu, Jessica, and Yu, Luping. Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells. United States: N. p., 2016. Web. doi:10.1021/acs.chemmater.5b04570.
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Zhao, Donglin, Wu, Qinghe, Cai, Zhengxu, Zheng, Tianyue, Chen, Wei, Lu, Jessica, & Yu, Luping. Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells. United States. https://doi.org/10.1021/acs.chemmater.5b04570
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Zhao, Donglin, Wu, Qinghe, Cai, Zhengxu, Zheng, Tianyue, Chen, Wei, Lu, Jessica, and Yu, Luping. Sat . "Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells". United States. https://doi.org/10.1021/acs.chemmater.5b04570. https://www.osti.gov/servlets/purl/1245464.
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@article{osti_1245464,
title = {Electron Acceptors Based on α-Substituted Perylene Diimide (PDI) for Organic Solar Cells},
author = {Zhao, Donglin and Wu, Qinghe and Cai, Zhengxu and Zheng, Tianyue and Chen, Wei and Lu, Jessica and Yu, Luping},
abstractNote = {The ortho-position functionalized perylene diimide derivatives (αPPID, αPBDT) were synthesized and used as the electron acceptors in nonfullerene organic photovoltaics. Due to the good planarity of ortho-position functionalized PDI, the αPPID and αPBDT show strong tendency to form aggregate because of their enhanced intermolecular pie-pie interaction. Moreover, they maintain the pure domains and the same packing order as in the pure film if they are blended with PBT7-TH and the SCLC measurement also shows the high electron mobility. The inverted OPVs employing αPDI-based compounds as acceptor and PBT7-TH as the donor give the highest PCE of 4.92 % for αPBDT based device and 3.61 % for αPPID based device, which is 39 % and 4 % higher than that for their counterpart βPBDT and βPPID. The charge separation study shows the more efficient exciton dissociation at interfaces between PDI based compounds and PBT7-TH. In conclusion, the results suggest that compared to beta-substituted ones, alpha-substituted PDI derivatives are more promising electron acceptors for OPV.},
doi = {10.1021/acs.chemmater.5b04570},
journal = {Chemistry of Materials},
number = 4,
volume = 28,
place = {United States},
year = {2016},
month = {2}
}
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https://doi.org/10.1021/acs.chemmater.5b04570
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    journal, January 2016

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    • Journal of Materials Chemistry C, Vol. 4, Issue 38
    • DOI: 10.1039/c6tc03476d

    9,9′-Bifluorenylidene-Core Perylene Diimide Acceptors for As-Cast Non-Fullerene Organic Solar Cells: The Isomeric Effect on Optoelectronic Properties
    journal, February 2018

    • Zhao, Yuan; Wang, Huan; Xia, Shengpeng
    • Chemistry - A European Journal, Vol. 24, Issue 16
    • DOI: 10.1002/chem.201705480

    Naphthalene core-based noncovalently fused-ring electron acceptors: effects of linkage positions on photovoltaic performances
    journal, January 2019

    • Zheng, Rui; Guo, Qingxin; Hao, Dan
    • Journal of Materials Chemistry C, Vol. 7, Issue 48
    • DOI: 10.1039/c9tc05013b

    Effects of conjugated bridges on the photovoltaic properties of ortho -functionalized perylene diimides for non-fullerene polymer solar cells
    journal, January 2018

    • Wu, Jiazun; Li, Xiangchun; Liu, Xiaodong
    • Journal of Materials Chemistry C, Vol. 6, Issue 48
    • DOI: 10.1039/c8tc03303j

    Isomeric N-Annulated Perylene Diimide Dimers for Organic Solar Cells
    journal, March 2018

    • Ma, Zetong; Fu, Huiting; Meng, Dong
    • Chemistry - An Asian Journal, Vol. 13, Issue 8
    • DOI: 10.1002/asia.201800058

    Synthesis and photophysical properties of pyridyl conjugated triazole appended naphthalenediimide derivatives
    journal, January 2019

    • Kumar, Girijesh; Guda, Ramu; Husain, Ahmad
    • Photochemical & Photobiological Sciences, Vol. 18, Issue 6
    • DOI: 10.1039/c9pp00003h

    Modulation of the power conversion efficiency of organic solar cells via architectural variation of a promising non-fullerene acceptor
    journal, January 2018

    • Mishra, Ruchika; Regar, Ramprasad; Singh, Varun
    • Journal of Materials Chemistry A, Vol. 6, Issue 2
    • DOI: 10.1039/c7ta08533h

    4,5,9,10-Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two-Photon Excited Emission
    journal, September 2017

    • Wu, Ze-Hua; Huang, Zhuo-Ting; Guo, Rui-Xue
    • Angewandte Chemie International Edition, Vol. 56, Issue 42
    • DOI: 10.1002/anie.201707529

    Simulations of absorption spectra of conjugated oligomers: role of planar conformation and aggregation in condensed phase
    journal, November 2017

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