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 in | Macromolecules Vol. 52; no. 10; pp. 3909 - 3917 |
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Main Authors | , |
Format | Journal Article |
Language | English |
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. |
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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 |
AuthorAffiliation_xml | – name: Department of Applied Chemistry, Graduate School of Engineering – name: Hiroshima University |
Author_xml | – sequence: 1 givenname: Tsubasa surname: Mikie fullname: Mikie, Tsubasa – sequence: 2 givenname: Itaru orcidid: 0000-0002-9879-2098 surname: Osaka fullname: Osaka, Itaru email: iosaka@hiroshima-u.ac.jp |
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CitedBy_id | crossref_primary_10_1021_acs_chemmater_1c00204 crossref_primary_10_1246_bcsj_20220093 crossref_primary_10_1002_adfm_202402974 crossref_primary_10_1016_j_solener_2021_03_004 crossref_primary_10_1246_bcsj_20200091 crossref_primary_10_1016_j_matchemphys_2022_126225 crossref_primary_10_1021_acs_macromol_1c00248 crossref_primary_10_1021_acsapm_9b00998 crossref_primary_10_1021_acs_chemmater_1c04196 |
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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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