Synthesis and Photophysical and Photovoltaic Properties of Porphyrin−Furan and −Thiophene Alternating Copolymers
Abstract
Conjugated polymers with alternating main chain structures of zinc porphyrin−furan (PZnPF) and zinc porphyrin−thiophene (PZnPT) have been synthesized by palladium(0)-catalyzed Stille coupling reaction. The optical, electrochemical, photophysical, and photovoltaic properties of PZnPF and PZnPT were investigated to elucidate the effects of the heterole bridges (i.e., furan vs. thiophene) in the porphyrin polymers. The optical bandgap of PZnPF (1.75 eV) is smaller than that of PZnPT (1.90 eV), implying the high delocalization of the π-electrons along the polymer main chain of PZnPF relative to PZnPT. The more extended π-conjugation in PZnPF results from the smaller steric repulsion of the meso -furan moiety with the porphyrin rings than that of the meso -thiophene. The time-resolved fluorescence spectrum of PZnPF showed a gradual Stokes shift to the longer wavelength in the subnanosecond time domain due to the relaxation from a twisted conformation with the large dihedral angles between the porphyrins and the furan rings to a coplanar conformation with the small dihedral angles, whereas the fluorescence spectrum of PZnPT did not exhibit the dynamic Stokes shift. Both PZnPF and PZnPT are electrochemically active in the oxidation and reduction regions and have suitable HOMO/LUMO levels that enable photoinduced electron transfer from the polymer to [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) in the blend films. Indeed, the blend films displayed strong fluorescence quenching…
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Porphyrins exhibit efficient electron transfer.
“they also exhibit e ffi cient electron transfer. 7,8”
From Recent progress in porphyrin-based materials for organic solar cells (2018) · cites this paper as [7]
Even when the efficiency of BHJ devices was inferior, these devices showed strong fluorescence quenching and charge-transfer emissions, indicating strong interactions between fullerenes and porphyrins.
“Even the e ffi ciency of BHJ devices was inferior; these devices showed strong uorescence quenching and chargetransfer (CT) emissions, which indicate strong interactions between fullerenes and porphyrins.”
From Recent progress in porphyrin-based materials for organic solar cells (2018) · cites this paper as [7]
A9 showed a PCE of 0.048%, which is higher than that of A10 (0.027%).
“A9 showed a PCE of 0.048%, which is higher than that of A10 (0.027%).”
From Recent progress in porphyrin-based materials for organic solar cells (2018) · cites this paper as [7]
Imahori et al. synthesized two porphyrin-furan (A9) and porphyrin-thiophene (A10) polymers using the Stille polycondensation reaction.
“Later, Imahori et al. synthesized two porphyrin -furan ( A9 ) and porphyrin -thiophene ( A10 ) polymers 7 using the Stille polycondensation reaction.”
From Recent progress in porphyrin-based materials for organic solar cells (2018) · cites this paper as [7]
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Recent progress in porphyrin-based materials for organic solar cells
Mahmood, A., Hu, J.-Y., Xiao, B., Tang, A., Wang, X., & Zhou, E. (2018) · Journal of Materials Chemistry A · doi:10.1039/c8ta06392c · Cited by 311 · see citing works
Wang, L., Shi, S., Ma, D., Chen, S., Gao, C., Wang, M., Shi, K., Li, Y., Li, X., & Wang, H. (2015) · Macromolecules · doi:10.1021/ma502050b · Cited by 39 · see citing works
- Authors
- Umeyama, T., Takamatsu, T., Tezuka, N., Matano, Y., Araki, Y., Wada, T., Yoshikawa, O., Sagawa, T., Yoshikawa, S., & Imahori, H.
- Affiliations
- Kyoto University (JP)
- Corresponding author
- Araki, Yasuyuki
- Imahori, Hiroshi
- Venue
- The Journal of Physical Chemistry C
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-05-21
- Volume
- 113
- Issue
- 24
- Pages
- 10798-10806
- ISSN
- 1932-7447 (ISSN-L)
- 1932-7455
- OpenAlex
- W2094747122
- Cited by
- 119
- References
- 0
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 3 · 2023: 3 · 2022: 2 · 2021: 4 · 2020: 7 · 2019: 3 · 2018: 2 · 2017: 8 · 2016: 7 · 2015: 11 · 2014: 10 · 2013: 7 · 2012: 20
- FWCI
- 7.73
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Physical Chemistry C (publishedVersion)
- Institutional Repositories DataBase (IRDB) (submittedVersion)
- Kyoto University Research Information Repository (Kyoto University) (submittedVersion)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Electronics and Photovoltaics
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Keywords
- alternating copolymers, π-conjugation, fluorescence quenching, photoinduced electron transfer, PCBM blends, bulk heterojunction solar cells, power conversion efficiency, photovoltaic performance, photophysical properties
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