Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance

Maryam Alsufyani; Marc-Antoine Stoeckel; Xingxing Chen; Karl Thorely; Rawad K Hallani; Yuttapoom Puttisong; Xudong Ji; Dilara Meli; Bryan D Paulsen; Joseph Strzalka; Khrystyna Regeta; Craig Combe; Hu Chen; Junfu Tian; Jonathan Rivnay; Simone Fabiano; Iain McCulloch

doi:10.1002/anie.202113078

Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance

Maryam Alsufyani, Marc-Antoine Stoeckel, Xingxing Chen, Karl Thorely, Rawad K Hallani, Yuttapoom Puttisong, Xudong Ji, Dilara Meli, Bryan D Paulsen, Joseph Strzalka, Khrystyna Regeta, Craig Combe, Hu Chen, Junfu Tian, Jonathan Rivnay, Simone Fabiano, Iain McCulloch

King Abdullah University of Science and Technology

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0% benzene (P-0), to 50% (P-50), and 75% (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S/cm and Power factors of 13.2 μWm−1 K−2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.

Original language	English (US)
Journal	Angewandte Chemie International Edition
DOIs	https://doi.org/10.1002/anie.202113078
State	Published - Nov 19 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-11-24
Acknowledged KAUST grant number(s): OSR-2018-CRG/CCF-3079, OSR-2018-CRG7-3749, OSR-2019-CRG8-4086
Acknowledgements: We acknowledge financial support from KAUST, including Office of Sponsored Research (OSR) awards no. OSR-2018-CRG/CCF-3079, OSR-2019-CRG8-4086 and OSR-2018-CRG7-3749. We acknowledge funding from ERC Synergy Grant SC2 (610115), the european union horizon 2020 research and innovation programme under grant agreement n°952911, project BOOSTER and grant agreement n°862474, project RoLA-FLEX, as well as EPSRC Project EP/T026219/1B.D.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308. This research used resources of the Advanced Photon Source (beamline 8-ID-E), a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357. The work at Linköping University was financially supported by the Knut and Alice Wallenberg foundation, the Swedish Research Council (2020 03243), Olle Engkvists Stiftelse (204-0256), the EC for the ITN projects HORATES (GA-955837), and the Swedish Government Strategic Research Area in Materials Science on Functional Materials at Linköping University (Faculty Grant SFO-Mat-LiU 2009-00971).

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.202113078

https://repository.kaust.edu.sa/bitstream/10754/673728/1/Lactone%20backbone_anie.202113078.pdf

Cite this

Alsufyani, M., Stoeckel, M.-A., Chen, X., Thorely, K., Hallani, R. K., Puttisong, Y., Ji, X., Meli, D., Paulsen, B. D., Strzalka, J., Regeta, K., Combe, C., Chen, H., Tian, J., Rivnay, J., Fabiano, S., & McCulloch, I. (2021). Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202113078

@article{60912c1f8f0548589397cc4ecd622359,

title = "Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance",

abstract = "Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0% benzene (P-0), to 50% (P-50), and 75% (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S/cm and Power factors of 13.2 μWm−1 K−2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.",

author = "Maryam Alsufyani and Marc-Antoine Stoeckel and Xingxing Chen and Karl Thorely and Hallani, {Rawad K} and Yuttapoom Puttisong and Xudong Ji and Dilara Meli and Paulsen, {Bryan D} and Joseph Strzalka and Khrystyna Regeta and Craig Combe and Hu Chen and Junfu Tian and Jonathan Rivnay and Simone Fabiano and Iain McCulloch",

note = "KAUST Repository Item: Exported on 2021-11-24 Acknowledged KAUST grant number(s): OSR-2018-CRG/CCF-3079, OSR-2018-CRG7-3749, OSR-2019-CRG8-4086 Acknowledgements: We acknowledge financial support from KAUST, including Office of Sponsored Research (OSR) awards no. OSR-2018-CRG/CCF-3079, OSR-2019-CRG8-4086 and OSR-2018-CRG7-3749. We acknowledge funding from ERC Synergy Grant SC2 (610115), the european union horizon 2020 research and innovation programme under grant agreement n°952911, project BOOSTER and grant agreement n°862474, project RoLA-FLEX, as well as EPSRC Project EP/T026219/1B.D.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308. This research used resources of the Advanced Photon Source (beamline 8-ID-E), a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357. The work at Link{\"o}ping University was financially supported by the Knut and Alice Wallenberg foundation, the Swedish Research Council (2020 03243), Olle Engkvists Stiftelse (204-0256), the EC for the ITN projects HORATES (GA-955837), and the Swedish Government Strategic Research Area in Materials Science on Functional Materials at Link{\"o}ping University (Faculty Grant SFO-Mat-LiU 2009-00971).",

year = "2021",

month = nov,

day = "19",

doi = "10.1002/anie.202113078",

language = "English (US)",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

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Alsufyani, M, Stoeckel, M-A, Chen, X, Thorely, K, Hallani, RK, Puttisong, Y, Ji, X, Meli, D, Paulsen, BD, Strzalka, J, Regeta, K, Combe, C, Chen, H, Tian, J, Rivnay, J, Fabiano, S & McCulloch, I 2021, 'Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance', Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202113078

TY - JOUR

T1 - Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance

AU - Alsufyani, Maryam

AU - Stoeckel, Marc-Antoine

AU - Chen, Xingxing

AU - Thorely, Karl

AU - Hallani, Rawad K

AU - Puttisong, Yuttapoom

AU - Ji, Xudong

AU - Meli, Dilara

AU - Paulsen, Bryan D

AU - Strzalka, Joseph

AU - Regeta, Khrystyna

AU - Combe, Craig

AU - Chen, Hu

AU - Tian, Junfu

AU - Rivnay, Jonathan

AU - Fabiano, Simone

AU - McCulloch, Iain

N1 - KAUST Repository Item: Exported on 2021-11-24 Acknowledged KAUST grant number(s): OSR-2018-CRG/CCF-3079, OSR-2018-CRG7-3749, OSR-2019-CRG8-4086 Acknowledgements: We acknowledge financial support from KAUST, including Office of Sponsored Research (OSR) awards no. OSR-2018-CRG/CCF-3079, OSR-2019-CRG8-4086 and OSR-2018-CRG7-3749. We acknowledge funding from ERC Synergy Grant SC2 (610115), the european union horizon 2020 research and innovation programme under grant agreement n°952911, project BOOSTER and grant agreement n°862474, project RoLA-FLEX, as well as EPSRC Project EP/T026219/1B.D.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308. This research used resources of the Advanced Photon Source (beamline 8-ID-E), a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357. The work at Linköping University was financially supported by the Knut and Alice Wallenberg foundation, the Swedish Research Council (2020 03243), Olle Engkvists Stiftelse (204-0256), the EC for the ITN projects HORATES (GA-955837), and the Swedish Government Strategic Research Area in Materials Science on Functional Materials at Linköping University (Faculty Grant SFO-Mat-LiU 2009-00971).

PY - 2021/11/19

Y1 - 2021/11/19

N2 - Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0% benzene (P-0), to 50% (P-50), and 75% (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S/cm and Power factors of 13.2 μWm−1 K−2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.

AB - Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0% benzene (P-0), to 50% (P-50), and 75% (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S/cm and Power factors of 13.2 μWm−1 K−2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.

UR - http://hdl.handle.net/10754/673728

UR - https://onlinelibrary.wiley.com/doi/10.1002/anie.202113078

U2 - 10.1002/anie.202113078

DO - 10.1002/anie.202113078

M3 - Article

C2 - 34797584

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance

Abstract

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