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Solution–Doped Donor–Acceptor Copolymers Based on Diketopyrrolopyrrole and 3, 3'–Bis (2–(2–(2–Methoxyethoxy) Ethoxy) ethoxy)–2, 2'–Bithiophene Exhibiting Outstanding Thermoelectric Power Factors with p–Dopants
Abstract
The design of polymeric semiconductors exhibiting high electrical conductivity (σ) and thermoelectric power factor (PF) will be vital for flexible large-area electronics. In this work, four polymers based on diketopyrrolopyrrole (DPP), 2,3-dihydrothieno[3,4-b][1,4]dioxine (EDOT), thieno[3,2-b]thiophene (TT), and 3, 3'-bis (2-(2-(2-methoxyethoxy) ethoxy) ethoxy)-2, 2'-bithiophene (MEET) are investigated as side-chains, with the MEET polymers newly synthesized for this study. These polymers are systematically doped with tetrafluorotetracyanoquinodimethane ( F4TCNQ), CF3SO3H, and the synthesized dopant Cp(CN)3-(COOMe)3, differing in geometry and electron affinity. The DPP-EDOT-based polymer containing MEET as side-chains exhibits the highest conductivity (σ) ≈700 S cm–1 in this series with the acidic dopant (CF3SO3H). This polymer also shows the lowest oxidation potential by cyclic voltammetry (CV), the strongest intermolecular interactions evidenced by differential scanning calorimetry (DSC), and has the most oxygen-based functionality for possible hydrogen bonding and ionic screening. Other polymers exhibit high σ ≈300–500 S cm–1 and power factor up to 300 µW m–1 K–2. The mechanism of conductivity is predominantly electronic, as validated by time-dependent conductance studies and transient thermo voltage monitoring over time, including for those doped with the acid. Furthermore, these materials maintain significant thermal stability and air stability over ≈6 weeks. Density functional theory calculations reveal molecular geometries andmore »
- Publication Date:
- Research Org.:
- Johns Hopkins University, Baltimore, MD (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 2309763
- Grant/Contract Number:
- FG02-07ER46465; 1708245; 2107360; OAC 1920103
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Advanced Functional Materials
- Additional Journal Information:
- Journal Volume: 34; Journal Issue: 7; Journal ID: ISSN 1616-301X
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; diketopyrrolopyrrole; conducting polymer; dopant; thermoelectric; power factor
Citation Formats
Mukhopadhyaya, Tushita, Wagner, Justine, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Melvin, Sophia J., Ji, Yuyang, Clancy, Paulette, Barman, Ishan, Thon, Susanna, Klausen, Rebekka S., and Katz, Howard E. Solution–Doped Donor–Acceptor Copolymers Based on Diketopyrrolopyrrole and 3, 3'–Bis (2–(2–(2–Methoxyethoxy) Ethoxy) ethoxy)–2, 2'–Bithiophene Exhibiting Outstanding Thermoelectric Power Factors with p–Dopants. United States: N. p., 2023.
Web. doi:10.1002/adfm.202309646.
Mukhopadhyaya, Tushita, Wagner, Justine, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Melvin, Sophia J., Ji, Yuyang, Clancy, Paulette, Barman, Ishan, Thon, Susanna, Klausen, Rebekka S., & Katz, Howard E. Solution–Doped Donor–Acceptor Copolymers Based on Diketopyrrolopyrrole and 3, 3'–Bis (2–(2–(2–Methoxyethoxy) Ethoxy) ethoxy)–2, 2'–Bithiophene Exhibiting Outstanding Thermoelectric Power Factors with p–Dopants. United States. https://doi.org/10.1002/adfm.202309646
Mukhopadhyaya, Tushita, Wagner, Justine, Lee, Taein D., Ganley, Connor, Tanwar, Swati, Raj, Piyush, Li, Lulin, Song, Yunjia, Melvin, Sophia J., Ji, Yuyang, Clancy, Paulette, Barman, Ishan, Thon, Susanna, Klausen, Rebekka S., and Katz, Howard E. Tue .
"Solution–Doped Donor–Acceptor Copolymers Based on Diketopyrrolopyrrole and 3, 3'–Bis (2–(2–(2–Methoxyethoxy) Ethoxy) ethoxy)–2, 2'–Bithiophene Exhibiting Outstanding Thermoelectric Power Factors with p–Dopants". United States. https://doi.org/10.1002/adfm.202309646.
@article{osti_2309763,
title = {Solution–Doped Donor–Acceptor Copolymers Based on Diketopyrrolopyrrole and 3, 3'–Bis (2–(2–(2–Methoxyethoxy) Ethoxy) ethoxy)–2, 2'–Bithiophene Exhibiting Outstanding Thermoelectric Power Factors with p–Dopants},
author = {Mukhopadhyaya, Tushita and Wagner, Justine and Lee, Taein D. and Ganley, Connor and Tanwar, Swati and Raj, Piyush and Li, Lulin and Song, Yunjia and Melvin, Sophia J. and Ji, Yuyang and Clancy, Paulette and Barman, Ishan and Thon, Susanna and Klausen, Rebekka S. and Katz, Howard E.},
abstractNote = {The design of polymeric semiconductors exhibiting high electrical conductivity (σ) and thermoelectric power factor (PF) will be vital for flexible large-area electronics. In this work, four polymers based on diketopyrrolopyrrole (DPP), 2,3-dihydrothieno[3,4-b][1,4]dioxine (EDOT), thieno[3,2-b]thiophene (TT), and 3, 3'-bis (2-(2-(2-methoxyethoxy) ethoxy) ethoxy)-2, 2'-bithiophene (MEET) are investigated as side-chains, with the MEET polymers newly synthesized for this study. These polymers are systematically doped with tetrafluorotetracyanoquinodimethane ( F4TCNQ), CF3SO3H, and the synthesized dopant Cp(CN)3-(COOMe)3, differing in geometry and electron affinity. The DPP-EDOT-based polymer containing MEET as side-chains exhibits the highest conductivity (σ) ≈700 S cm–1 in this series with the acidic dopant (CF3SO3H). This polymer also shows the lowest oxidation potential by cyclic voltammetry (CV), the strongest intermolecular interactions evidenced by differential scanning calorimetry (DSC), and has the most oxygen-based functionality for possible hydrogen bonding and ionic screening. Other polymers exhibit high σ ≈300–500 S cm–1 and power factor up to 300 µW m–1 K–2. The mechanism of conductivity is predominantly electronic, as validated by time-dependent conductance studies and transient thermo voltage monitoring over time, including for those doped with the acid. Furthermore, these materials maintain significant thermal stability and air stability over ≈6 weeks. Density functional theory calculations reveal molecular geometries and inform about frontier energy levels. Raman spectroscopy, in conjunction with scanning electron microscopy (SEM-EDS) and x-ray diffraction, provides insight into the solid-state microstructure and degree of phase separation of the doped polymer films. Infrared spectroscopy enables this study to further quantify the degree of charge transfer from polymer to dopant.},
doi = {10.1002/adfm.202309646},
journal = {Advanced Functional Materials},
number = 7,
volume = 34,
place = {United States},
year = {Tue Oct 31 00:00:00 EDT 2023},
month = {Tue Oct 31 00:00:00 EDT 2023}
}
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