Nonfullerene Acceptors Bearing Spiro‐Substituted Bithiophene Units in Organic Solar Cells: Tuning the Frontier Molecular Orbital Distribution to Reduce Exciton Binding Energy

Abstract The development of nonfullerene acceptors (NFAs), represented by ITIC , has contributed to improving the power conversion efficiency (PCE) of organic solar cells (OSCs). Although tuning the electronic structures to reduce the exciton binding energy ( E b ) is considered to promote photocharge generation, a rational molecular design for NFAs has not been established. In this study, we designed and developed two ITIC ‐based NFAs bearing spiro‐substituted bithiophene or biphenyl units (named SpiroT‐DCI and SpiroF‐DCI ) to tune the frontier molecular orbital (FMO) distribution of NFAs. While the highest occupied molecular orbitals (HOMOs) of SpiroF‐DCI and ITIC are delocalized in the main π‐conjugated framework, the HOMO of SpiroT‐DCI is distributed on the bithiophene unit. Reflecting this difference, SpiroT‐DCI exhibits a smaller E b than either SpiroF‐DCI or ITIC , and exhibits greater external quantum efficiency in single‐component OSCs. Furthermore, SpiroT‐DCI shows improved PCEs for bulk‐heterojunction OSCs with a donor of PBDB‐T, compared with that of either SpiroT‐DCI or ITIC . Time‐resolved spectroscopy measurements show that the photo‐induced intermolecular charge separation is effective even in pristine SpiroT‐DCI films. This study highlights the introduction of spiro‐substituted bithiophene units that are effective in tuning the FMOs of ITIC , which is desirable for reducing the E b and improving the PCE in OSCs.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-08-12
DOI
https://doi.org/10.1002/anie.202412691
Citations
11
Primary Topic
Organic Electronics and Photovoltaics
Type
article
Field-Weighted Citation Impact
2.30

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article

Nonfullerene Acceptors Bearing Spiro‐Substituted Bithiophene Units in Organic Solar Cells: Tuning the Frontier Molecular Orbital Distribution to Reduce Exciton Binding Energy

Takumi Urakami, Yasuhiro Kobori, Masahiro Higashi, Akira Yamakata et al.
11 citations
Angewandte Chemie International Edition
Organic Electronics and Photovoltaics
2.30
article

Nonfullerene Acceptors Bearing Spiro‐Substituted Bithiophene Units in Organic Solar Cells: Tuning the Frontier Molecular Orbital Distribution to Reduce Exciton Binding Energy

Takumi Urakami, Yasuhiro Kobori, Masahiro Higashi, Akira Yamakata, Hirofumi Sato, Seihou Jinnai, Yutaka Ie, Kai Wang, Sota Tsujimura, Rintaro Adachi
article en
11 citations

Abstract

Abstract The development of nonfullerene acceptors (NFAs), represented by ITIC , has contributed to improving the power conversion efficiency (PCE) of organic solar cells (OSCs). Although tuning the electronic structures to reduce the exciton binding energy ( E b ) is considered to promote photocharge generation, a rational molecular design for NFAs has not been established. In this study, we designed and developed two ITIC ‐based NFAs bearing spiro‐substituted bithiophene or biphenyl units (named SpiroT‐DCI and SpiroF‐DCI ) to tune the frontier molecular orbital (FMO) distribution of NFAs. While the highest occupied molecular orbitals (HOMOs) of SpiroF‐DCI and ITIC are delocalized in the main π‐conjugated framework, the HOMO of SpiroT‐DCI is distributed on the bithiophene unit. Reflecting this difference, SpiroT‐DCI exhibits a smaller E b than either SpiroF‐DCI or ITIC , and exhibits greater external quantum efficiency in single‐component OSCs. Furthermore, SpiroT‐DCI shows improved PCEs for bulk‐heterojunction OSCs with a donor of PBDB‐T, compared with that of either SpiroT‐DCI or ITIC . Time‐resolved spectroscopy measurements show that the photo‐induced intermolecular charge separation is effective even in pristine SpiroT‐DCI films. This study highlights the introduction of spiro‐substituted bithiophene units that are effective in tuning the FMOs of ITIC , which is desirable for reducing the E b and improving the PCE in OSCs.

Angewandte Chemie International EditionVol. 63(47)
Okayama University (JP), Kyoto University (JP), Kyoto University of Education (JP), Osaka Research Institute of Industrial Science and Technology (JP), Nagoya University (JP), Kobe University (JP), The University of Osaka (JP)
New Energy and Industrial Technology Development Organization, Mitsubishi Foundation
Affordable and clean energy
Openalex Percentile: Top 11%
Organic Electronics and Photovoltaics
2.30
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