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Title: A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics

Authors:
 [1];  [1];  [2];  [3];  [4];  [5];  [6];  [7];  [1];  [1];  [8];  [8];  [3]; ORCiD logo [9];  [10]
  1. Laboratory of Organic Electronics, Department of Science and Technology, Linköping University, SE-601 74 Norrköping Sweden
  2. 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
  3. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Road Evanston IL 60208 USA
  4. Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr Germany
  5. Leibniz-Institut für Polymerforschung Dresden e.V., D-010 69 Dresden Germany
  6. Department of Physics, Chemistry and Biology, Linköping University, SE-581 83 Linköping Sweden
  7. Flexterra Corporation, 8025 Lamon Avenue Skokie IL 60077 USA
  8. Technische Universität Dresden, Center for Advancing Electronics Dresden, D-01062 Dresden Germany; Leibniz-Institut für Polymerforschung Dresden e.V., D-010 69 Dresden Germany
  9. 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
  10. 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:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
FOREIGN
OSTI Identifier:
1466048
Resource Type:
Journal Article
Journal Name:
Advanced Materials
Additional Journal Information:
Journal Volume: 30; Journal Issue: 31; Journal ID: ISSN 0935-9648
Publisher:
Wiley
Country of Publication:
United States
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. United States: 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. United States. 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, and Facchetti, Antonio. Wed . "A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics". United States. doi:10.1002/adma.201801898.
@article{osti_1466048,
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 = {},
doi = {10.1002/adma.201801898},
journal = {Advanced Materials},
issn = {0935-9648},
number = 31,
volume = 30,
place = {United States},
year = {2018},
month = {6}
}

Works referenced in this record:

Charge-transport model for conducting polymers
journal, November 2016

  • Kang, Stephen Dongmin; Snyder, G. Jeffrey
  • Nature Materials, Vol. 16, Issue 2
  • DOI: 10.1038/nmat4784

A high-mobility electron-transporting polymer for printed transistors
journal, January 2009

  • Yan, He; Chen, Zhihua; Zheng, Yan
  • Nature, Vol. 457, Issue 7230, p. 679-686
  • DOI: 10.1038/nature07727

Role of Polymer Structure on the Conductivity of N-Doped Polymers
journal, March 2016

  • Naab, Benjamin D.; Gu, Xiaodan; Kurosawa, Tadanori
  • Advanced Electronic Materials, Vol. 2, Issue 5
  • DOI: 10.1002/aelm.201600004

Conductivity and power factor enhancement of n-type semiconducting polymers using sodium silica gel dopant
journal, August 2017

  • Madan, Deepa; Zhao, Xingang; Ireland, Robert M.
  • APL Materials, Vol. 5, Issue 8
  • DOI: 10.1063/1.4990139

Materials and Applications for Large Area Electronics: Solution-Based Approaches
journal, January 2010

  • Arias, Ana Claudia; MacKenzie, J. Devin; McCulloch, Iain
  • Chemical Reviews, Vol. 110, Issue 1
  • DOI: 10.1021/cr900150b

Moderate doping leads to high performance of semiconductor/insulator polymer blend transistors
journal, March 2013

  • Lu, Guanghao; Blakesley, James; Himmelberger, Scott
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2587

Doped polymer semiconductors with ultrahigh and ultralow work functions for ohmic contacts
journal, November 2016

  • Tang, Cindy G.; Ang, Mervin C. Y.; Choo, Kim-Kian
  • Nature, Vol. 539, Issue 7630
  • DOI: 10.1038/nature20133

Unconventional, Chemically Stable, and Soluble Two-Dimensional Angular Polycyclic Aromatic Hydrocarbons: From Molecular Design to Device Applications
journal, December 2014

  • Zhang, Lei; Cao, Yang; Colella, Nicholas S.
  • Accounts of Chemical Research, Vol. 48, Issue 3, p. 500-509
  • DOI: 10.1021/ar500278w

Mechanistic Insight into Catalyst-Transfer Polymerization of Unusual Anion-Radical Naphthalene Diimide Monomers: An Observation of Ni(0) Intermediates
journal, September 2012

  • Senkovskyy, Volodymyr; Tkachov, Roman; Komber, Hartmut
  • Macromolecules, Vol. 45, Issue 19
  • DOI: 10.1021/ma301797w

Microfluidic Crystal Engineering of π-Conjugated Polymers
journal, July 2015


A Universal Method to Produce Low-Work Function Electrodes for Organic Electronics
journal, April 2012


Correlating the Seebeck coefficient of thermoelectric polymer thin films to their charge transport mechanism
journal, January 2018


Thermoelectric Properties of Solution-Processed n-Doped Ladder-Type Conducting Polymers
journal, October 2016


Enhancing Molecular n-Type Doping of Donor-Acceptor Copolymers by Tailoring Side Chains
journal, January 2018


Experimental evidence that short-range intermolecular aggregation is sufficient for efficient charge transport in conjugated polymers
journal, August 2015

  • Wang, Suhao; Fabiano, Simone; Himmelberger, Scott
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 34
  • DOI: 10.1073/pnas.1501381112

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
  • DOI: 10.1039/C6CS00149A

Correlation of Seebeck coefficient and electric conductivity in polyaniline and polypyrrole
journal, March 1998

  • Mateeva, N.; Niculescu, H.; Schlenoff, J.
  • Journal of Applied Physics, Vol. 83, Issue 6
  • DOI: 10.1063/1.367119

Optimization of the thermoelectric figure of merit in the conducting polymer poly(3,4-ethylenedioxythiophene)
journal, May 2011

  • Bubnova, Olga; Khan, Zia Ullah; Malti, Abdellah
  • Nature Materials, Vol. 10, Issue 6, p. 429-433
  • DOI: 10.1038/nmat3012

Aggregation control in natural brush-printed conjugated polymer films and implications for enhancing charge transport
journal, November 2017

  • Wang, Gang; Huang, Wei; Eastham, Nicholas D.
  • Proceedings of the National Academy of Sciences, Vol. 114, Issue 47
  • DOI: 10.1073/pnas.1713634114

Defect-free Naphthalene Diimide Bithiophene Copolymers with Controlled Molar Mass and High Performance via Direct Arylation Polycondensation
journal, May 2015

  • Matsidik, Rukiya; Komber, Hartmut; Luzio, Alessandro
  • Journal of the American Chemical Society, Vol. 137, Issue 20
  • DOI: 10.1021/jacs.5b03355

High Conductivity and Electron-Transfer Validation in an n-Type Fluoride-Anion-Doped Polymer for Thermoelectrics in Air
journal, July 2017


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
  • DOI: 10.1002/adma.201304866

Control of Ambipolar and Unipolar Transport in Organic Transistors by Selective Inkjet-Printed Chemical Doping for High Performance Complementary Circuits
journal, August 2014

  • Khim, Dongyoon; Baeg, Kang-Jun; Caironi, Mario
  • Advanced Functional Materials, Vol. 24, Issue 40
  • DOI: 10.1002/adfm.201400850

How intermolecular geometrical disorder affects the molecular doping of donor–acceptor copolymers
journal, March 2015

  • Di Nuzzo, Daniele; Fontanesi, Claudio; Jones, Rebecca
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms7460

Impact of the Doping Method on Conductivity and Thermopower in Semiconducting Polythiophenes
journal, October 2014

  • Glaudell, Anne M.; Cochran, Justin E.; Patel, Shrayesh N.
  • Advanced Energy Materials, Vol. 5, Issue 4
  • DOI: 10.1002/aenm.201401072

Molecular Doping Enhances Photoconductivity in Polymer Bulk Heterojunction Solar Cells
journal, September 2013

  • Zhang, Yuan; Zhou, Huiqiong; Seifter, Jason
  • Advanced Materials, Vol. 25, Issue 48
  • DOI: 10.1002/adma.201302159

Rylene and Related Diimides for Organic Electronics
journal, December 2010

  • Zhan, Xiaowei; Facchetti, Antonio; Barlow, Stephen
  • Advanced Materials, Vol. 23, Issue 2, p. 268-284
  • DOI: 10.1002/adma.201001402

Molecular Design and Synthetic Approaches to Electron-Transporting Organic Transistor Semiconductors
journal, February 2011

  • Jung, Byung Jun; Tremblay, Noah J.; Yeh, Ming-Ling
  • Chemistry of Materials, Vol. 23, Issue 3
  • DOI: 10.1021/cm102296d

Quantum-Chemical Insights into the Prediction of Charge Transport Parameters for a Naphthalenetetracarboxydiimide-Based Copolymer with Enhanced Electron Mobility
journal, November 2011

  • Fazzi, Daniele; Caironi, Mario; Castiglioni., Chiara
  • Journal of the American Chemical Society, Vol. 133, Issue 47
  • DOI: 10.1021/ja208824d

Doping of organic semiconductors
journal, December 2012


Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics
journal, January 2018


Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers
journal, December 2011

  • Senkovskyy, Volodymyr; Tkachov, Roman; Komber, Hartmut
  • Journal of the American Chemical Society, Vol. 133, Issue 49
  • DOI: 10.1021/ja208710x

Effective Solution- and Vacuum-Processed n-Doping by Dimers of Benzimidazoline Radicals
journal, April 2014

  • Naab, Benjamin D.; Zhang, Siyuan; Vandewal, Koen
  • Advanced Materials, Vol. 26, Issue 25
  • DOI: 10.1002/adma.201400668

Doping of Conjugated Polythiophenes with Alkyl Silanes
journal, June 2009

  • Kao, Chi Yueh; Lee, Bumsu; Wielunski, Leszek S.
  • Advanced Functional Materials, Vol. 19, Issue 12, p. 1906-1911
  • DOI: 10.1002/adfm.200900120

One-Pot Synthesis of All-Conjugated Block-Like Bisthiophene–Naphthalenediimide/Fluorene Copolymer
journal, July 2014

  • Tkachov, Roman; Komber, Hartmut; Rauch, Sebastian
  • Macromolecules, Vol. 47, Issue 15
  • DOI: 10.1021/ma5006588

Ultrahigh Mobility in Polymer Field-Effect Transistors by Design
journal, March 2011

  • Tsao, Hoi Nok; Cho, Don M.; Park, Insun
  • Journal of the American Chemical Society, Vol. 133, Issue 8
  • DOI: 10.1021/ja108861q

Semi-metallic polymers
journal, December 2013

  • Bubnova, Olga; Khan, Zia Ullah; Wang, Hui
  • Nature Materials, Vol. 13, Issue 2
  • DOI: 10.1038/nmat3824

Morphology controls the thermoelectric power factor of a doped semiconducting polymer
journal, June 2017

  • Patel, Shrayesh N.; Glaudell, Anne M.; Peterson, Kelly A.
  • Science Advances, Vol. 3, Issue 6
  • DOI: 10.1126/sciadv.1700434

Design of Semiconducting Indacenodithiophene Polymers for High Performance Transistors and Solar Cells
journal, January 2012

  • McCulloch, Iain; Ashraf, Raja Shahid; Biniek, Laure
  • Accounts of Chemical Research, Vol. 45, Issue 5
  • DOI: 10.1021/ar200208g

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
  • DOI: 10.1021/jacs.5b00945

π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications
journal, February 2011


Poly(ethylene imine) Impurities Induce n-doping Reaction in Organic (Semi)Conductors
journal, July 2014

  • Fabiano, Simone; Braun, Slawomir; Liu, Xianjie
  • Advanced Materials, Vol. 26, Issue 34
  • DOI: 10.1002/adma.201401986

Range and energetics of charge hopping in organic semiconductors
journal, December 2017


Preparation of halogenated derivatives of thiazolo[5,4- d ]thiazole via direct electrophilic aromatic substitution
journal, May 2008

  • Benin, Vladimir; Yeates, Alan T.; Dudis, Douglas
  • Journal of Heterocyclic Chemistry, Vol. 45, Issue 3
  • DOI: 10.1002/jhet.5570450328

Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers
journal, October 2017

  • Eckstein, Brian J.; Melkonyan, Ferdinand S.; Manley, Eric F.
  • Journal of the American Chemical Society, Vol. 139, Issue 41
  • DOI: 10.1021/jacs.7b07750

Asymmetric electron and hole transport in a high-mobility n -type conjugated polymer
journal, October 2012


Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units
journal, November 2016


High Conductivity in Molecularly p-Doped Diketopyrrolopyrrole-Based Polymer: The Impact of a High Dopant Strength and Good Structural Order
journal, May 2016

  • Karpov, Yevhen; Erdmann, Tim; Raguzin, Ivan
  • Advanced Materials, Vol. 28, Issue 28
  • DOI: 10.1002/adma.201506295

Tetraaminoethylenes
journal, May 1965

  • Winberg, H. E.; Carnahan, J. E.; Coffman, D. D.
  • Journal of the American Chemical Society, Vol. 87, Issue 9
  • DOI: 10.1021/ja01087a040

Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
journal, June 2017


Color Tuning in Polymer Light-Emitting Diodes with Lewis Acids
journal, June 2012

  • Zalar, Peter; Henson, Zachary B.; Welch, Gregory C.
  • Angewandte Chemie International Edition, Vol. 51, Issue 30
  • DOI: 10.1002/anie.201202570

Very Low Degree of Energetic Disorder as the Origin of High Mobility in an n-channel Polymer Semiconductor
journal, July 2011

  • Caironi, Mario; Bird, Matt; Fazzi, Daniele
  • Advanced Functional Materials, Vol. 21, Issue 17
  • DOI: 10.1002/adfm.201100592

The chemical and structural origin of efficient p-type doping in P3HT
journal, May 2013