A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics
Abstract
Abstract The synthesis of a novel naphthalenediimide (NDI)‐bithiazole (Tz2)‐based polymer [P(NDI2OD‐Tz2)] is reported, and structural, thin‐film morphological, as well as charge transport and thermoelectric properties are compared to the parent and widely investigated NDI‐bithiophene (T2) polymer [P(NDI2OD‐T2)]. Since the steric repulsions in Tz2 are far lower than in T2, P(NDI2OD‐Tz2) exhibits a more planar and rigid backbone, enhancing π–π chain stacking and intermolecular interactions. In addition, the electron‐deficient nature of Tz2 enhances the polymer electron affinity, thus reducing the polymer donor–acceptor character. When n‐doped with amines, P(NDI2OD‐Tz2) achieves electrical conductivity (≈0.1 S cm −1 ) and a power factor (1.5 µW m −1 K −2 ) far greater than those of P(NDI2OD‐T2) (0.003 S cm −1 and 0.012 µW m −1 K −2 , respectively). These results demonstrate that planarized NDI‐based polymers with reduced donor–acceptor character can achieve substantial electrical conductivity and thermoelectric response.
- Authors:
-
[9];
- Laboratory of Organic Electronics Department of Science and Technology Linköping University SE‐601 74 Norrköping Sweden
- Technische Universität Dresden Center for Advancing Electronics Dresden D‐01062 Dresden Germany, Leibniz‐Institut für Polymerforschung Dresden e.V. D‐010 69 Dresden Germany, Flexterra Corporation 8025 Lamon Avenue Skokie IL 60077 USA
- Department of Chemistry and the Materials Research Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
- Max‐Planck‐Institut für Kohlenforschung Kaiser‐Wilhelm‐Platz 1 D‐45470 Mülheim an der Ruhr Germany
- Leibniz‐Institut für Polymerforschung Dresden e.V. D‐010 69 Dresden Germany
- Department of Physics Chemistry and Biology Linköping University SE‐581 83 Linköping Sweden
- Flexterra Corporation 8025 Lamon Avenue Skokie IL 60077 USA
- Technische Universität Dresden Center for Advancing Electronics Dresden D‐01062 Dresden Germany, Leibniz‐Institut für Polymerforschung Dresden e.V. D‐010 69 Dresden Germany
- Laboratory of Organic Electronics Department of Science and Technology Linköping University SE‐601 74 Norrköping Sweden, Flexterra Corporation 8025 Lamon Avenue Skokie IL 60077 USA, Department of Chemistry and the Materials Research Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
- Flexterra Corporation 8025 Lamon Avenue Skokie IL 60077 USA, Department of Chemistry and the Materials Research Center Northwestern University 2145 Sheridan Road Evanston IL 60208 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1456281
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Advanced Materials
- Additional Journal Information:
- Journal Name: Advanced Materials Journal Volume: 30 Journal Issue: 31; Journal ID: ISSN 0935-9648
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Wang, Suhao, Sun, Hengda, Erdmann, Tim, Wang, Gang, Fazzi, Daniele, Lappan, Uwe, Puttisong, Yuttapoom, Chen, Zhihua, Berggren, Magnus, Crispin, Xavier, Kiriy, Anton, Voit, Brigitte, Marks, Tobin J., Fabiano, Simone, and Facchetti, Antonio. A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics. Germany: N. p., 2018.
Web. doi:10.1002/adma.201801898.
Wang, Suhao, Sun, Hengda, Erdmann, Tim, Wang, Gang, Fazzi, Daniele, Lappan, Uwe, Puttisong, Yuttapoom, Chen, Zhihua, Berggren, Magnus, Crispin, Xavier, Kiriy, Anton, Voit, Brigitte, Marks, Tobin J., Fabiano, Simone, & Facchetti, Antonio. A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics. Germany. https://doi.org/10.1002/adma.201801898
Wang, Suhao, Sun, Hengda, Erdmann, Tim, Wang, Gang, Fazzi, Daniele, Lappan, Uwe, Puttisong, Yuttapoom, Chen, Zhihua, Berggren, Magnus, Crispin, Xavier, Kiriy, Anton, Voit, Brigitte, Marks, Tobin J., Fabiano, Simone, and Facchetti, Antonio. Thu .
"A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics". Germany. https://doi.org/10.1002/adma.201801898.
@article{osti_1456281,
title = {A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics},
author = {Wang, Suhao and Sun, Hengda and Erdmann, Tim and Wang, Gang and Fazzi, Daniele and Lappan, Uwe and Puttisong, Yuttapoom and Chen, Zhihua and Berggren, Magnus and Crispin, Xavier and Kiriy, Anton and Voit, Brigitte and Marks, Tobin J. and Fabiano, Simone and Facchetti, Antonio},
abstractNote = {Abstract The synthesis of a novel naphthalenediimide (NDI)‐bithiazole (Tz2)‐based polymer [P(NDI2OD‐Tz2)] is reported, and structural, thin‐film morphological, as well as charge transport and thermoelectric properties are compared to the parent and widely investigated NDI‐bithiophene (T2) polymer [P(NDI2OD‐T2)]. Since the steric repulsions in Tz2 are far lower than in T2, P(NDI2OD‐Tz2) exhibits a more planar and rigid backbone, enhancing π–π chain stacking and intermolecular interactions. In addition, the electron‐deficient nature of Tz2 enhances the polymer electron affinity, thus reducing the polymer donor–acceptor character. When n‐doped with amines, P(NDI2OD‐Tz2) achieves electrical conductivity (≈0.1 S cm −1 ) and a power factor (1.5 µW m −1 K −2 ) far greater than those of P(NDI2OD‐T2) (0.003 S cm −1 and 0.012 µW m −1 K −2 , respectively). These results demonstrate that planarized NDI‐based polymers with reduced donor–acceptor character can achieve substantial electrical conductivity and thermoelectric response.},
doi = {10.1002/adma.201801898},
journal = {Advanced Materials},
number = 31,
volume = 30,
place = {Germany},
year = {Thu Jun 21 00:00:00 EDT 2018},
month = {Thu Jun 21 00:00:00 EDT 2018}
}
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