Ester-Functionalized Naphthobispyrazine as an Acceptor Building Unit for Semiconducting Polymers: Synthesis, Properties, and Photovoltaic Performance

Strongly electron-deficient π-conjugated systems are key building units for semiconducting polymers that are used in organic electronic devices, such as organic photovoltaic (OPV) cells. Here, we designed and synthesized a naphthobispyrazine derivative bearing four ester groups (eNPz) as a new elect...

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Published inMacromolecules Vol. 52; no. 10; pp. 3909 - 3917
Main Authors Mikie, Tsubasa, Osaka, Itaru
Format Journal Article
LanguageEnglish
Published American Chemical Society 28.05.2019
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Abstract Strongly electron-deficient π-conjugated systems are key building units for semiconducting polymers that are used in organic electronic devices, such as organic photovoltaic (OPV) cells. Here, we designed and synthesized a naphthobispyrazine derivative bearing four ester groups (eNPz) as a new electron-deficient building unit and three eNPz-based semiconducting polymers with different donor units, that is, bithiophene (PeNPz2T), terthiophene (PeNPz3T), and quaterthiophene (PeNPz4T). These new polymers have relatively deep lowest unoccupied molecular orbital (LUMO) energy levels of around −3.5 eV, along with narrow optical band gaps of around 1.5 eV. The LUMO energy levels and the optical band gaps are significantly deeper and narrower than those of a polymer based on alkylated naphthobispyrazine. The results indicate that eNPz has a strong electron deficiency. The polymers show reasonably high power conversion efficiency of more than 6% in OPV cells in combination with a fullerene derivative. This study demonstrates that eNPz can be a useful building unit for high-performance semiconducting polymers.
AbstractList Strongly electron-deficient π-conjugated systems are key building units for semiconducting polymers that are used in organic electronic devices, such as organic photovoltaic (OPV) cells. Here, we designed and synthesized a naphthobispyrazine derivative bearing four ester groups (eNPz) as a new electron-deficient building unit and three eNPz-based semiconducting polymers with different donor units, that is, bithiophene (PeNPz2T), terthiophene (PeNPz3T), and quaterthiophene (PeNPz4T). These new polymers have relatively deep lowest unoccupied molecular orbital (LUMO) energy levels of around −3.5 eV, along with narrow optical band gaps of around 1.5 eV. The LUMO energy levels and the optical band gaps are significantly deeper and narrower than those of a polymer based on alkylated naphthobispyrazine. The results indicate that eNPz has a strong electron deficiency. The polymers show reasonably high power conversion efficiency of more than 6% in OPV cells in combination with a fullerene derivative. This study demonstrates that eNPz can be a useful building unit for high-performance semiconducting polymers.
Author Osaka, Itaru
Mikie, Tsubasa
AuthorAffiliation Department of Applied Chemistry, Graduate School of Engineering
Hiroshima University
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Title Ester-Functionalized Naphthobispyrazine as an Acceptor Building Unit for Semiconducting Polymers: Synthesis, Properties, and Photovoltaic Performance
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