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Synthesis of 5 H-Dithieno[3,2-b:2′,3′-d]pyran as an Electron-Rich Building Block for Donor–Acceptor Type Low-Bandgap Polymers
Abstract
We describe the detailed synthesis and characterization of an electron-rich building block, dithienopyran (DTP), and its application as a donor unit in low-bandgap conjugated polymers. The electron-donating property of the DTP unit was found to be the strongest among the most frequently used donor units such as benzodithiophene (BDT) or cyclopentadithiophene (CPDT) units. When the DTP unit was polymerized with the strongly electron-deficient difluorobenzothiadiazole (DFBT) unit, a regiorandom polymer (PDTP–DFBT, bandgap = 1.38 eV) was obtained. For comparison with the DTP unit, polymers containing alternating benzodithiophene (BDT) or cyclopentadithiophene (CPDT) units and the DFBT unit were synthesized (PBDT–DFBT and PCPDT–DFBT). We found that the DTP based polymer PDTP–DFBT shows significantly improved solubility and processability compared to the BDT or CPDT based polymers. Consequently, very high molecular weight and soluble PDTP–DFBT can be obtained with less bulky side chains. Interestingly, PDTP–DFBT shows excellent performance in bulk-heterojunction solar cells with power conversion efficiencies reaching 8.0%, which is significantly higher than PBDT–DFBT and PCPDT–DFBT based devices. This study demonstrates that DTP is a promising building block for high-performance solar cell materials.
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Coffin, R. C., Peet, J., Rogers, J., & Bazan, G. C. (2009) · Nature Chemistry · doi:10.1038/nchem.403 · Cited by 597
Cited by
Porphyrin‐Based Bulk Heterojunction Organic Photovoltaics: The Rise of the Colors of Life
Kesters, J., Verstappen, P., Kelchtermans, M., Lutsen, L., Vanderzande, D., & Maes, W. (2015) · Advanced Energy Materials · doi:10.1002/aenm.201500218 · Cited by 193
Porphyrin‐Incorporated 2D D–A Polymers with Over 8.5% Polymer Solar Cell Efficiency
Chao, Y., Jheng, J., Wu, J., Wu, K., Peng, H., Tsai, M., Wang, C., Hsiao, Y., Wang, C., Lin, C., et al. (2014) · Advanced Materials · doi:10.1002/adma.201401345 · Cited by 119
Yang, K., Chen, Z., Wang, Y., & Guo, X. (2023) · Accounts of Materials Research · doi:10.1021/accountsmr.2c00237 · Cited by 72
Metadata
- Authors
- Dou, L., Chen, C.-C., Yoshimura, K., Ohya, K., Chang, W.-H., Gao, J., Liu, Y., Richard, E., & Yang, Y.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-04-26
- Volume
- 46
- Issue
- 9
- Pages
- 3384-3390
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W4242013550
- Cited by
- 310
- References
- 1
- FWCI
- 34.35
- Type
- journal article
- Language
- en
- Open access
- closed
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- Dou, L., Chen, C.-C., Yoshimura, K., Ohya, K., Chang, W.-H., Gao, J., Liu, Y., Richard, E., & Yang, Y. (2013). Synthesis of 5 H-Dithieno[3,2-b:2′,3′-d]pyran as an Electron-Rich Building Block for Donor–Acceptor Type Low-Bandgap Polymers. Macromolecules. https://doi.org/10.1021/ma400452j
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