Dichlorinated Dithienylethene-Based Copolymers for Air-Stable n-Type Conductivity and Thermoelectricity
Abstract
Here, two donor-acceptor polymers were obtained by coupling difluoro- and dichloro-substituted forms of the electron-deficient unit BDOPV and the relatively weak donor moiety dichlorodithienylethene (ClTVT). The conductivity and power factors of doped devices are different for the chlorinated and fluorinated BDOPV polymers. High electron conductivity of 38.3 and 16.1 S cm-1 were obtained from the chlorinated and fluorinated polymers with N-DMBI, respectively, and 12.4 and 2.4 S cm-1 were obtained from the chlorinated and fluorinated polymers with CoCp2, respectively, from drop-cast devices. The corresponding power factors are 22.7, 7.6, 39.5 and 8.0 μW m-1 K-2, respectively. Doping of PClClTVT with N-DMBI results in excellent air-stability; the electron conductivity of devices with 50 mol% N-DMBI as dopant remained up to 4.9 S m-1 after 222 days in the air, the longest for an n-doped polymer stored in air, with a thermoelectric power factor of 9.3 μW m-1 K-2. However, the conductivity of PFClTVT-based devices can hardly be measured after 103 days. These observations are consistent with morphologies determined by grazing incidence wide angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM). The results demonstrate that chemical structures leading to dense and ordered packing can enhance electron conductivity and air stability ofmore »
- Authors:
-
- Johns Hopkins Univ., Baltimore, MD (United States)
- Univ. of Massachusetts, Amherst, MA (United States)
- Univ. of Massachusetts, Amherst, MA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Publication Date:
- Research Org.:
- Johns Hopkins Univ., Baltimore, MD (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); US Department of the Navy, Office of Naval Research (ONR)
- OSTI Identifier:
- 1773756
- Alternate Identifier(s):
- OSTI ID: 1804245
- Grant/Contract Number:
- FG02-07ER46465; 1708245; N00014-17-1-2241
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Advanced Functional Materials
- Additional Journal Information:
- Journal Volume: 31; Journal Issue: 5; Journal ID: ISSN 1616-301X
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 30 DIRECT ENERGY CONVERSION; 36 MATERIALS SCIENCE; dichlorinated dithienylethene; air stability; n-type; organic thermoelectricity
Citation Formats
Han, Jinfeng, Fan, Huidong, Zhang, Qingyang, Hu, Qin, Russell, Thomas P., and Katz, Howard E. Dichlorinated Dithienylethene-Based Copolymers for Air-Stable n-Type Conductivity and Thermoelectricity. United States: N. p., 2020.
Web. doi:10.1002/adfm.202005901.
Han, Jinfeng, Fan, Huidong, Zhang, Qingyang, Hu, Qin, Russell, Thomas P., & Katz, Howard E. Dichlorinated Dithienylethene-Based Copolymers for Air-Stable n-Type Conductivity and Thermoelectricity. United States. https://doi.org/10.1002/adfm.202005901
Han, Jinfeng, Fan, Huidong, Zhang, Qingyang, Hu, Qin, Russell, Thomas P., and Katz, Howard E. Fri .
"Dichlorinated Dithienylethene-Based Copolymers for Air-Stable n-Type Conductivity and Thermoelectricity". United States. https://doi.org/10.1002/adfm.202005901. https://www.osti.gov/servlets/purl/1773756.
@article{osti_1773756,
title = {Dichlorinated Dithienylethene-Based Copolymers for Air-Stable n-Type Conductivity and Thermoelectricity},
author = {Han, Jinfeng and Fan, Huidong and Zhang, Qingyang and Hu, Qin and Russell, Thomas P. and Katz, Howard E.},
abstractNote = {Here, two donor-acceptor polymers were obtained by coupling difluoro- and dichloro-substituted forms of the electron-deficient unit BDOPV and the relatively weak donor moiety dichlorodithienylethene (ClTVT). The conductivity and power factors of doped devices are different for the chlorinated and fluorinated BDOPV polymers. High electron conductivity of 38.3 and 16.1 S cm-1 were obtained from the chlorinated and fluorinated polymers with N-DMBI, respectively, and 12.4 and 2.4 S cm-1 were obtained from the chlorinated and fluorinated polymers with CoCp2, respectively, from drop-cast devices. The corresponding power factors are 22.7, 7.6, 39.5 and 8.0 μW m-1 K-2, respectively. Doping of PClClTVT with N-DMBI results in excellent air-stability; the electron conductivity of devices with 50 mol% N-DMBI as dopant remained up to 4.9 S m-1 after 222 days in the air, the longest for an n-doped polymer stored in air, with a thermoelectric power factor of 9.3 μW m-1 K-2. However, the conductivity of PFClTVT-based devices can hardly be measured after 103 days. These observations are consistent with morphologies determined by grazing incidence wide angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM). The results demonstrate that chemical structures leading to dense and ordered packing can enhance electron conductivity and air stability of n-type donor-acceptor polymers.},
doi = {10.1002/adfm.202005901},
journal = {Advanced Functional Materials},
number = 5,
volume = 31,
place = {United States},
year = {Fri Oct 23 00:00:00 EDT 2020},
month = {Fri Oct 23 00:00:00 EDT 2020}
}
Works referenced in this record:
Solubility-Limited Extrinsic n-Type Doping of a High Electron Mobility Polymer for Thermoelectric Applications
journal, January 2014
- Schlitz, Ruth A.; Brunetti, Fulvio G.; Glaudell, Anne M.
- Advanced Materials, Vol. 26, Issue 18
Chloride transport in conductive polymer films for an n-type thermoelectric platform
journal, January 2020
- Kim, Byeonggwan; Hwang, Jong Un; Kim, Eunkyoung
- Energy & Environmental Science, Vol. 13, Issue 3
Conducting polymers: Efficient thermoelectric materials
journal, February 2011
- Dubey, Nidhi; Leclerc, Mario
- Journal of Polymer Science Part B: Polymer Physics, Vol. 49, Issue 7
Enhancing the n-Type Conductivity and Thermoelectric Performance of Donor-Acceptor Copolymers through Donor Engineering
journal, September 2018
- Yang, Chi-Yuan; Jin, Wen-Long; Wang, Jue
- Advanced Materials, Vol. 30, Issue 43
Thermoelectric generators: A review of applications
journal, May 2017
- Champier, Daniel
- Energy Conversion and Management, Vol. 140
Polymer Composites for Thermoelectric Applications
journal, December 2014
- McGrail, Brendan T.; Sehirlioglu, Alp; Pentzer, Emily
- Angewandte Chemie International Edition, Vol. 54, Issue 6
Organic Thermoelectric Materials: Emerging Green Energy Materials Converting Heat to Electricity Directly and Efficiently
journal, March 2014
- Zhang, Qian; Sun, Yimeng; Xu, Wei
- Advanced Materials, Vol. 26, Issue 40
Solution processed organic thermoelectrics: towards flexible thermoelectric modules
journal, January 2015
- Chen, Yani; Zhao, Yan; Liang, Ziqi
- Energy & Environmental Science, Vol. 8, Issue 2
Organic thermoelectric materials for energy harvesting and temperature control
journal, August 2016
- Russ, Boris; Glaudell, Anne; Urban, Jeffrey J.
- Nature Reviews Materials, Vol. 1, Issue 10
Thermoelectric Properties of PEDOT:PSS
journal, February 2019
- Fan, Zeng; Ouyang, Jianyong
- Advanced Electronic Materials, Vol. 5, Issue 11
Selenium‐Substituted Diketopyrrolopyrrole Polymer for High‐Performance p‐Type Organic Thermoelectric Materials
journal, December 2019
- Ding, Jiamin; Liu, Zitong; Zhao, Wenrui
- Angewandte Chemie International Edition, Vol. 58, Issue 52
Progress in Nickel‐Coordinated Polymers as Intrinsically Conducting n‐Type Thermoelectric Materials
journal, February 2019
- Menon, Akanksha K.; Wolfe, Rylan M. W.; Kommandur, Sampath
- Advanced Electronic Materials, Vol. 5, Issue 11
Thermally Driven Large N-Type Voltage Responses from Hybrids of Carbon Nanotubes and Poly(3,4-ethylenedioxythiophene) with Tetrakis(dimethylamino)ethylene
journal, October 2015
- Wang, Hong; Hsu, Jui-Hung; Yi, Su-In
- Advanced Materials, Vol. 27, Issue 43
Flexible n-Type High-Performance Thermoelectric Thin Films of Poly(nickel-ethylenetetrathiolate) Prepared by an Electrochemical Method
journal, March 2016
- Sun, Yuanhui; Qiu, Lin; Tang, Liangpo
- Advanced Materials, Vol. 28, Issue 17
Toward High Performance n -Type Thermoelectric Materials by Rational Modification of BDPPV Backbones
journal, May 2015
- Shi, Ke; Zhang, Fengjiao; Di, Chong-An
- Journal of the American Chemical Society, Vol. 137, Issue 22
Enhanced Molecular Packing of a Conjugated Polymer with High Organic Thermoelectric Power Factor
journal, September 2016
- Ma, Wei; Shi, Ke; Wu, Yang
- ACS Applied Materials & Interfaces, Vol. 8, Issue 37
Understanding the Effects of Molecular Dopant on n‐Type Organic Thermoelectric Properties
journal, May 2019
- Un, Hio‐Ieng; Gregory, Shawn A.; Mohapatra, Swagat K.
- Advanced Energy Materials, Vol. 9, Issue 24
A thermally activated and highly miscible dopant for n-type organic thermoelectrics
journal, July 2020
- Yang, Chi-Yuan; Ding, Yi-Fan; Huang, Dazhen
- Nature Communications, Vol. 11, Issue 1
Doping Dependent In‐Plane and Cross‐Plane Thermoelectric Performance of Thin n‐Type Polymer P(NDI2OD‐T2) Films
journal, May 2020
- Kluge, Regina M.; Saxena, Nitin; Chen, Wei
- Advanced Functional Materials, Vol. 30, Issue 28
Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics
journal, November 2019
- Yan, Xinwen; Xiong, Miao; Li, Jia-Tong
- Journal of the American Chemical Society, Vol. 141, Issue 51
Naphthodithiophenediimide–Benzobisthiadiazole-Based Polymers: Versatile n-Type Materials for Field-Effect Transistors and Thermoelectric Devices
journal, January 2017
- Wang, Yang; Nakano, Masahiro; Michinobu, Tsuyoshi
- Macromolecules, Vol. 50, Issue 3
Strategies To Enhance the Conductivity of n-Type Polymer Thermoelectric Materials
journal, December 2018
- Lu, Yang; Wang, Jie-Yu; Pei, Jian
- Chemistry of Materials, Vol. 31, Issue 17
Development of n-type organic semiconductors for thin film transistors: a viewpoint of molecular design
journal, January 2014
- Gao, Xike; Hu, Yunbin
- J. Mater. Chem. C, Vol. 2, Issue 17
A Solution-Doped Polymer Semiconductor:Insulator Blend for Thermoelectrics
journal, September 2016
- Kiefer, David; Yu, Liyang; Fransson, Erik
- Advanced Science, Vol. 4, Issue 1
Solution-processed organic thermoelectric materials exhibiting doping-concentration-dependent polarity
journal, January 2016
- Hwang, Sunbin; Potscavage, William J.; Yang, Yu Seok
- Physical Chemistry Chemical Physics, Vol. 18, Issue 42
A Novel Solution-Processable n-Dopant Based on 1,4-Dihydropyridine Motif for High Electrical Conductivity of Organic Semiconductors
journal, August 2017
- Shi, Ke; Lu, Zuo-Yu; Yu, Zi-Di
- Advanced Electronic Materials, Vol. 3, Issue 11
Beating the thermodynamic limit with photo-activation of n-doping in organic semiconductors
journal, November 2017
- Lin, Xin; Wegner, Berthold; Lee, Kyung Min
- Nature Materials, Vol. 16, Issue 12
High Conductivity and Electron-Transfer Validation in an n-Type Fluoride-Anion-Doped Polymer for Thermoelectrics in Air
journal, July 2017
- Zhao, Xingang; Madan, Deepa; Cheng, Yan
- Advanced Materials, Vol. 29, Issue 34
N-type doping of an electron-transport material by controlled gas-phase incorporation of cobaltocene
journal, November 2006
- Chan, Calvin K.; Amy, Fabrice; Zhang, Qing
- Chemical Physics Letters, Vol. 431, Issue 1-3, p. 67-71
Modification of the Poly(bisdodecylquaterthiophene) Structure for High and Predominantly Nonionic Conductivity with Matched Dopants
journal, August 2017
- Li, Hui; DeCoster, Mallory E.; Ireland, Robert M.
- Journal of the American Chemical Society, Vol. 139, Issue 32
Self-Stabilized Nanoparticles of Intrinsically Conducting Copolymers from 5-Sulfonic-2-Anisidine
journal, August 2008
- Li, Xin-Gui; Lü, Qiu-Feng; Huang, Mei-Rong
- Small, Vol. 4, Issue 8
Optimization of Polymerization Conditions of Furan with Aniline for Variable Conducting Polymers
journal, September 2006
- Li, Xin-Gui; Kang, Yan; Huang, Mei-Rong
- Journal of Combinatorial Chemistry, Vol. 8, Issue 5
Novel Multifunctional Polymers from Aromatic Diamines by Oxidative Polymerizations
journal, September 2002
- Li, Xin-Gui; Huang, Mei-Rong; Duan, Wei
- Chemical Reviews, Vol. 102, Issue 9
Effect of Heteroatom and Doping on the Thermoelectric Properties of Poly(3-alkylchalcogenophenes)
journal, October 2018
- Gregory, Shawn A.; Menon, Akanksha K.; Ye, Shuyang
- Advanced Energy Materials, Vol. 8, Issue 34
Thermoelectric plastics: from design to synthesis, processing and structure–property relationships
journal, January 2016
- Kroon, Renee; Mengistie, Desalegn Alemu; Kiefer, David
- Chemical Society Reviews, Vol. 45, Issue 22