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Title: Intra-molecular Charge Transfer and Electron Delocalization in Non-fullerene Organic Solar Cells

Abstract

Two types of electron acceptors were synthesized by coupling two kinds of electron-rich cores with four equivalent perylene diimides (PDIs) at the a position. With fully aromatic cores, TPB and TPSe have pi-orbitals spread continuously over the whole aromatic conjugated backbone, unlike TPC and TPSi, which contain isolated PDI units due to the use of a tetrahedron carbon or silicon linker. Density functional theory calculations of the projected density of states showed that the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) for TPB are localized in separate regions of space. Further, the LUMO of TPB shows a greater contribution from the orbitals belonging to the connective core of the molecules than that of TPC. Overall, the properties of the HOMO and LUMO point at increased intra-molecular delocalization of negative charge carriers for TPB and TPSe than for TPC and TPSi and hence at a more facile intra-molecular charge transfer for the former. The film absorption and emission spectra showed evidences for the inter -molecular electron delocalization in TPB and TPSe, which is consistent with the network structure revealed by X-ray diffraction studies on single crystals of TPB. These features benefit the formation of charge transfer statesmore » and/or facilitate charge transport. Thus, higher electron mobility and higher charge dissociation probabilities under Jsc condition were observed in blend films of TPB:PTB7-Th and TPSe:PTB7-Th than those in TPC:PTB7Th and TPSi:PTB7-Th blend films. As a result, the Jsc and fill factor values of 15.02 mA/cm2, 0.58 and 14.36 mA/cm2, 0.55 for TPB- and TPSe-based solar cell are observed, whereas those for TPC and TPSi are 11.55 mA/cm2, 0.47 and 10.35 mA/cm2, 0.42, respectively.« less

Authors:
ORCiD logo [1];  [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [2];  [4]; ORCiD logo [2]; ORCiD logo [4]; ORCiD logo [4];  [4];  [2]
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  1. Shantou Univ., Guangdong (China). Dept. of Chemistry, Key Lab. for Preparation and Application of Ordered Structural Materials of Guangdong Province
  2. Univ. of Chicago, IL (United States). Dept. of Chemistry, The James Franck Inst.
  3. Univ. of Chicago, IL (United States). Inst. for Molecular Engineering
  4. Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division, Inst. for Molecular Engineering; 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)
OSTI Identifier:
1433912
Grant/Contract Number:  
AC02-06CH11357; SC0001059; DMR-1263006; CHE-1346572
Resource Type:
Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 10; Journal Issue: 12; Journal ID: ISSN 1944-8244
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
25 ENERGY STORAGE; 14 SOLAR ENERGY; electron delocalization; intra-molecular charge transfer; non-fullerene electron acceptor; organic solar cell; perylene diimide

Citation Formats

Wu, Qinghe, Zhao, Donglin, Goldey, Matthew B., Filatov, Alexander S., Sharapov, Valerii, Colon, Yamil J., Cai, Zhengxu, Chen, Wei, de Pablo, Juan, Galli, Giulia, and Yu, Luping. Intra-molecular Charge Transfer and Electron Delocalization in Non-fullerene Organic Solar Cells. United States: N. p., 2018. Web. doi:10.1021/acsami.7b18717.
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Wu, Qinghe, Zhao, Donglin, Goldey, Matthew B., Filatov, Alexander S., Sharapov, Valerii, Colon, Yamil J., Cai, Zhengxu, Chen, Wei, de Pablo, Juan, Galli, Giulia, & Yu, Luping. Intra-molecular Charge Transfer and Electron Delocalization in Non-fullerene Organic Solar Cells. United States. doi:10.1021/acsami.7b18717.
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Wu, Qinghe, Zhao, Donglin, Goldey, Matthew B., Filatov, Alexander S., Sharapov, Valerii, Colon, Yamil J., Cai, Zhengxu, Chen, Wei, de Pablo, Juan, Galli, Giulia, and Yu, Luping. Fri . "Intra-molecular Charge Transfer and Electron Delocalization in Non-fullerene Organic Solar Cells". United States. doi:10.1021/acsami.7b18717. https://www.osti.gov/servlets/purl/1433912.
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@article{osti_1433912,
title = {Intra-molecular Charge Transfer and Electron Delocalization in Non-fullerene Organic Solar Cells},
author = {Wu, Qinghe and Zhao, Donglin and Goldey, Matthew B. and Filatov, Alexander S. and Sharapov, Valerii and Colon, Yamil J. and Cai, Zhengxu and Chen, Wei and de Pablo, Juan and Galli, Giulia and Yu, Luping},
abstractNote = {Two types of electron acceptors were synthesized by coupling two kinds of electron-rich cores with four equivalent perylene diimides (PDIs) at the a position. With fully aromatic cores, TPB and TPSe have pi-orbitals spread continuously over the whole aromatic conjugated backbone, unlike TPC and TPSi, which contain isolated PDI units due to the use of a tetrahedron carbon or silicon linker. Density functional theory calculations of the projected density of states showed that the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) for TPB are localized in separate regions of space. Further, the LUMO of TPB shows a greater contribution from the orbitals belonging to the connective core of the molecules than that of TPC. Overall, the properties of the HOMO and LUMO point at increased intra-molecular delocalization of negative charge carriers for TPB and TPSe than for TPC and TPSi and hence at a more facile intra-molecular charge transfer for the former. The film absorption and emission spectra showed evidences for the inter -molecular electron delocalization in TPB and TPSe, which is consistent with the network structure revealed by X-ray diffraction studies on single crystals of TPB. These features benefit the formation of charge transfer states and/or facilitate charge transport. Thus, higher electron mobility and higher charge dissociation probabilities under Jsc condition were observed in blend films of TPB:PTB7-Th and TPSe:PTB7-Th than those in TPC:PTB7Th and TPSi:PTB7-Th blend films. As a result, the Jsc and fill factor values of 15.02 mA/cm2, 0.58 and 14.36 mA/cm2, 0.55 for TPB- and TPSe-based solar cell are observed, whereas those for TPC and TPSi are 11.55 mA/cm2, 0.47 and 10.35 mA/cm2, 0.42, respectively.},
doi = {10.1021/acsami.7b18717},
journal = {ACS Applied Materials and Interfaces},
number = 12,
volume = 10,
place = {United States},
year = {2018},
month = {3}
}
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Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI:  10.1021/acsami.7b18717
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Cited by: 11 works
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Figures / Tables:

Figure 1 Figure 1: (a) J-V curves, (b) External quantum efficiency spectrum and (c) Photocurrent density (Jph) versus effective voltage (Veff) characteristics for solar cells with PTB7-Th as donor and TPC, TPSi, TPB or TPSe as acceptor.
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Works referencing / citing this record:

Meta-analysis: the molecular organization of non-fullerene acceptors
journal, January 2020

  • Mondelli, Pierluigi; Boschetto, Gabriele; Horton, Peter N.
  • Materials Horizons
  • DOI: 10.1039/c9mh01439j

Meta-analysis: the molecular organization of non-fullerene acceptors
journal, January 2020

  • Mondelli, Pierluigi; Boschetto, Gabriele; Horton, Peter N.
  • Materials Horizons
  • DOI: 10.1039/c9mh01439j

Perylene diimide based star-shaped small molecular acceptors for high efficiency organic solar cells
journal, January 2019

  • Wang, Hang; Li, Miao; Liu, Yahui
  • Journal of Materials Chemistry C, Vol. 7, Issue 4
  • DOI: 10.1039/c8tc05332d

Electronic and optical properties of π-bridged perylenediimide derivatives: the role of π-bridges
journal, January 2019

  • Guo, Yuan; Han, Guangchao; Tu, Zeyi
  • Journal of Materials Chemistry A, Vol. 7, Issue 20
  • DOI: 10.1039/c9ta03124c

Electronic structure at coarse-grained resolutions from supervised machine learning
journal, March 2019

  • Jackson, Nicholas E.; Bowen, Alec S.; Antony, Lucas W.
  • Science Advances, Vol. 5, Issue 3
  • DOI: 10.1126/sciadv.aav1190

Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood
journal, March 2019

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