Facile Synthesis of Polycyclic Aromatic Hydrocarbon (PAH)–Based Acceptors with Fine-Tuned Optoelectronic Properties

Toward Efficient Additive-Free Nonfullerene Organic Solar Cells

Yang Wang, Bin Liu, Chang Woo Koh, Xin Zhou, Huiliang Sun, Jianwei Yu, Kun Yang, Hang Wang, Qiaogan Liao, Han Young Woo, Xugang Guo

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A series of polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated cores (from naphthalene, anthracene, pyrene, to perylene) are incorporated into nonfullerene acceptors for the first time. Four different fused-ring electron acceptors (FREAs), i.e., DTN-IC-2Ph, DTA-IC-3Ph, DTP-IC-4Ph, and DTPy-IC-5Ph, are prepared via simple and facile synthetic procedures, yielding a remarkable platform to study the structure–property relationship for nonfullerene solar cells. With the PAH core being extended systematically, the gradually redshifted absorption with enhanced molar extinction coefficient (ε) is realized, the energy level of the highest occupied molecular orbital is up-shifted, and the electron mobility is greatly enhanced. Meanwhile, the solubility decreases and the molecular packing becomes strengthened. As a result, with an optimized combination of these characteristics, DTP-IC-4Ph attains good solubility, high molar extinction coefficient, complementary absorption, suitable morphology, well-matched energy levels, as well as efficient charge dissociation and transport in blend film. Consequently, the DTP-IC-4Ph-based solar cells with a donor polymer, poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b′]dithiophene))-alt-(5,5-(1′,3′-di-2-thienyl-5′,7′-bis(2-ethylhexyl)benzo[1′,2′-c:4′,5′-c′]dithiophene-4,8-dione))] (PBDB-T) exhibit a promising power conversion efficiency of 10.37% without any additives, which is close to the best performance achieved in additive-free nonfullerene solar cells (NFSCs). The results demonstrate that the PAH building blocks have great potential for the construction of novel FREAs for efficient additive-free NFSCs.

Original languageEnglish
Article number1803976
JournalAdvanced Energy Materials
DOIs
Publication statusPublished - 2019 Jan 1

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Polycyclic Aromatic Hydrocarbons
Polycyclic aromatic hydrocarbons
Optoelectronic devices
Solar cells
Electron energy levels
Solubility
Perylene
Electrons
Anthracene
Electron mobility
Pyrene
Molecular orbitals
Naphthalene
Differential thermal analysis
Conversion efficiency
Polymers
Organic solar cells

Keywords

  • additive-free
  • low-cost
  • nonfullerene organic solar cells
  • polycyclic aromatic hydrocarbon
  • structure–property relationship

ASJC Scopus subject areas

  • Renewable Energy, Sustainability and the Environment
  • Materials Science(all)

Cite this

Facile Synthesis of Polycyclic Aromatic Hydrocarbon (PAH)–Based Acceptors with Fine-Tuned Optoelectronic Properties : Toward Efficient Additive-Free Nonfullerene Organic Solar Cells. / Wang, Yang; Liu, Bin; Koh, Chang Woo; Zhou, Xin; Sun, Huiliang; Yu, Jianwei; Yang, Kun; Wang, Hang; Liao, Qiaogan; Woo, Han Young; Guo, Xugang.

In: Advanced Energy Materials, 01.01.2019.

Research output: Contribution to journalArticle

Wang, Yang ; Liu, Bin ; Koh, Chang Woo ; Zhou, Xin ; Sun, Huiliang ; Yu, Jianwei ; Yang, Kun ; Wang, Hang ; Liao, Qiaogan ; Woo, Han Young ; Guo, Xugang. / Facile Synthesis of Polycyclic Aromatic Hydrocarbon (PAH)–Based Acceptors with Fine-Tuned Optoelectronic Properties : Toward Efficient Additive-Free Nonfullerene Organic Solar Cells. In: Advanced Energy Materials. 2019.
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abstract = "A series of polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated cores (from naphthalene, anthracene, pyrene, to perylene) are incorporated into nonfullerene acceptors for the first time. Four different fused-ring electron acceptors (FREAs), i.e., DTN-IC-2Ph, DTA-IC-3Ph, DTP-IC-4Ph, and DTPy-IC-5Ph, are prepared via simple and facile synthetic procedures, yielding a remarkable platform to study the structure–property relationship for nonfullerene solar cells. With the PAH core being extended systematically, the gradually redshifted absorption with enhanced molar extinction coefficient (ε) is realized, the energy level of the highest occupied molecular orbital is up-shifted, and the electron mobility is greatly enhanced. Meanwhile, the solubility decreases and the molecular packing becomes strengthened. As a result, with an optimized combination of these characteristics, DTP-IC-4Ph attains good solubility, high molar extinction coefficient, complementary absorption, suitable morphology, well-matched energy levels, as well as efficient charge dissociation and transport in blend film. Consequently, the DTP-IC-4Ph-based solar cells with a donor polymer, poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b′]dithiophene))-alt-(5,5-(1′,3′-di-2-thienyl-5′,7′-bis(2-ethylhexyl)benzo[1′,2′-c:4′,5′-c′]dithiophene-4,8-dione))] (PBDB-T) exhibit a promising power conversion efficiency of 10.37{\%} without any additives, which is close to the best performance achieved in additive-free nonfullerene solar cells (NFSCs). The results demonstrate that the PAH building blocks have great potential for the construction of novel FREAs for efficient additive-free NFSCs.",
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author = "Yang Wang and Bin Liu and Koh, {Chang Woo} and Xin Zhou and Huiliang Sun and Jianwei Yu and Kun Yang and Hang Wang and Qiaogan Liao and Woo, {Han Young} and Xugang Guo",
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AU - Liu, Bin

AU - Koh, Chang Woo

AU - Zhou, Xin

AU - Sun, Huiliang

AU - Yu, Jianwei

AU - Yang, Kun

AU - Wang, Hang

AU - Liao, Qiaogan

AU - Woo, Han Young

AU - Guo, Xugang

PY - 2019/1/1

Y1 - 2019/1/1

N2 - A series of polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated cores (from naphthalene, anthracene, pyrene, to perylene) are incorporated into nonfullerene acceptors for the first time. Four different fused-ring electron acceptors (FREAs), i.e., DTN-IC-2Ph, DTA-IC-3Ph, DTP-IC-4Ph, and DTPy-IC-5Ph, are prepared via simple and facile synthetic procedures, yielding a remarkable platform to study the structure–property relationship for nonfullerene solar cells. With the PAH core being extended systematically, the gradually redshifted absorption with enhanced molar extinction coefficient (ε) is realized, the energy level of the highest occupied molecular orbital is up-shifted, and the electron mobility is greatly enhanced. Meanwhile, the solubility decreases and the molecular packing becomes strengthened. As a result, with an optimized combination of these characteristics, DTP-IC-4Ph attains good solubility, high molar extinction coefficient, complementary absorption, suitable morphology, well-matched energy levels, as well as efficient charge dissociation and transport in blend film. Consequently, the DTP-IC-4Ph-based solar cells with a donor polymer, poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b′]dithiophene))-alt-(5,5-(1′,3′-di-2-thienyl-5′,7′-bis(2-ethylhexyl)benzo[1′,2′-c:4′,5′-c′]dithiophene-4,8-dione))] (PBDB-T) exhibit a promising power conversion efficiency of 10.37% without any additives, which is close to the best performance achieved in additive-free nonfullerene solar cells (NFSCs). The results demonstrate that the PAH building blocks have great potential for the construction of novel FREAs for efficient additive-free NFSCs.

AB - A series of polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated cores (from naphthalene, anthracene, pyrene, to perylene) are incorporated into nonfullerene acceptors for the first time. Four different fused-ring electron acceptors (FREAs), i.e., DTN-IC-2Ph, DTA-IC-3Ph, DTP-IC-4Ph, and DTPy-IC-5Ph, are prepared via simple and facile synthetic procedures, yielding a remarkable platform to study the structure–property relationship for nonfullerene solar cells. With the PAH core being extended systematically, the gradually redshifted absorption with enhanced molar extinction coefficient (ε) is realized, the energy level of the highest occupied molecular orbital is up-shifted, and the electron mobility is greatly enhanced. Meanwhile, the solubility decreases and the molecular packing becomes strengthened. As a result, with an optimized combination of these characteristics, DTP-IC-4Ph attains good solubility, high molar extinction coefficient, complementary absorption, suitable morphology, well-matched energy levels, as well as efficient charge dissociation and transport in blend film. Consequently, the DTP-IC-4Ph-based solar cells with a donor polymer, poly[(2,6-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-b:4,5-b′]dithiophene))-alt-(5,5-(1′,3′-di-2-thienyl-5′,7′-bis(2-ethylhexyl)benzo[1′,2′-c:4′,5′-c′]dithiophene-4,8-dione))] (PBDB-T) exhibit a promising power conversion efficiency of 10.37% without any additives, which is close to the best performance achieved in additive-free nonfullerene solar cells (NFSCs). The results demonstrate that the PAH building blocks have great potential for the construction of novel FREAs for efficient additive-free NFSCs.

KW - additive-free

KW - low-cost

KW - nonfullerene organic solar cells

KW - polycyclic aromatic hydrocarbon

KW - structure–property relationship

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