Download PDF
CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 223-228
DOI: 10.1055/s-0040-1714145
Short Communication

A Water-Dispersible Quinoid-Resonant Conducting Polymer for Organic Electronics

Dafei Yuan 
a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
,
Xiaozhang Zhu 
a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
› Author Affiliations Funding Information We thank the National Key Research and Development Program of China (No. 2019YFA0705900 and 2017YFA0204701) funded by MOST and the National Natural Science Foundation of China (No. 21661132006, 21572234, and 91833304) for the financial support.
› Further Information
   Permissions and Reprints All articles of this category


Abstract

Developing stable and solution-processable highly conductive polymers has been the research goal in organic electronics since the first demonstration of metallic conductive polyacetylene. Here, we used a unique quinoid-resonant building block thieno[3,4-b]thiophene (TbT) to develop a new water-dispersible conducting polymer, PTbT-Me:PSS. Linear polymerization and large surfactant counterion, poly(styrenesulfonate) (PSS−), were introduced, which enabled a high electrical conductivity of 68 S cm−1 and exhibited water-dispersible property. Interchain bipolaron was found in PTbT-Me:PSS when compared with polaron in PEDOT:PSS in their conducting mechanism. Moreover, we applied this highly conductive PTbT-Me:PSS as the solution-processed polymer thermoelectric material and a decent power factor of 3.1 μW m−1 K−2 was achieved.

Key words

conducting polymers - solution-processed - electronic devices - organic thermoelectric materials - energy conversion

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1714145.


Supporting Information



Publication History

Received: 11 May 2020

Accepted: 04 June 2020

Article published online:
20 August 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Heeger AJ. Angew. Chem. Int. Ed. 2001; 40: 2591
    CrossrefPubMed
      • 2
    • 2a Shirakawa H, Louis EJ, MacDiarmid AG, Chiang CK, Heeger AJ. J. Chem. Soc., Chem. Commun. 1977; 578
      CrossrefPubMed
    • 2b Naarmann H, Theophilou N. Synth. Met. 1987; 22: 1
      CrossrefPubMed
    • 2c Park YW. Synth. Met. 1991; 45: 173
      CrossrefPubMed
      3
    • 3a Cao Y, Treacy GM, Smith P, Heeger AJ. Synth. Met. 1993; 57: 3526
      CrossrefPubMed
    • 3b Toshima N. Macromol. Symp. 2002; 186: 81
      CrossrefPubMed
    • 3c Li J, Tang X, Li H, Yan Y, Zhang Q. Synth. Met. 2010; 160: 1153
      CrossrefPubMed
  • 4 Yan H, Ohta T, Toshima N. Macromol. Mater. Eng. 2001; 286: 139
    CrossrefPubMed
  • 5 Kirchmeyer S, Reuter K. J. Mater. Chem. 2005; 15: 2077
    CrossrefPubMed
  • 6 Chen R, Sun K, Zhang Q, Zhou Y, Li M, Sun Y, Wu Z, Wu Y, Li X, Xi J, Ma C, Zhang Y, Ouyang J. iScience 2019; 12: 66
    CrossrefPubMed
      • 7
    • 7a Yano H, Kudo K, Marumo K, Okuzaki H. Sci. Adv. 2019; 5: v9492
      CrossrefPubMed
    • 7b Zotti G, Zecchin S, Schiavon G, Groenendaal LB. Macromol. Chem. Phys. 2002; 203: 1958
      CrossrefPubMed
    • 7c Persson KM, Karlsson R, Svennersten K, Loffler S, Jager EW, Richter-Dahlfors A, Konradsson P, Berggren M. Adv. Mater. 2011; 23: 4403
      CrossrefPubMed
      8
    • 8a Kawase T, Sirringhaus H, Friend RH, Shimoda T. Adv. Mater. 2001; 13: 1601
      CrossrefPubMed
    • 8b Okuzaki H, Ishihara M, Ashizawa S. Synth. Met. 2003; 137: 947
      CrossrefPubMed
  • 9 Gustafsson JC, Liedberg B, Inganäs O. Solid State Ionics 1994; 69: 145
    CrossrefPubMed
  • 10 Zhang F, Johansson M, Andersson MR, Hummelen JC, Inganäs O. Adv. Mater. 2002; 14: 662
    CrossrefPubMed
  • 11 Burroughes JH, Bradley DD. C, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB. Nature 1990; 347: 539
    CrossrefPubMed
  • 12 Jonas F, Morrison JT. Synth. Met. 1997; 85: 1397
    CrossrefPubMed
      • 13
    • 13a Kim B, Shin H, Park T, Lim H, Kim E. Adv. Mater. 2013; 25: 5483
      CrossrefPubMed
    • 13b Kim GH, Shao L, Zhang K, Pipe KP. Nat. Mater. 2013; 12: 719
      CrossrefPubMed
    • 13c Bubnova O, Khan ZU, Wang H, Braun S, Evans DR, Fabretto M, Hojati-Talemi P, Dagnelund D, Arlin JB, Geerts YH, Desbief S, Breiby DW, Andreasen JW, Lazzaroni R, Chen WM, Zozoulenko I, Fahlman M, Murphy PJ, Berggren M, Crispin X. Nat. Mater. 2014; 13: 190
      CrossrefPubMed
    • 13d Shi W, Zhao T, Xi J, Wang D, Shuai Z. J. Am. Chem. Soc. 2015; 137: 12929
      CrossrefPubMed
    • 13e Weathers A, Khan ZU, Brooke R, Evans D, Pettes MT, Andreasen JW, Crispin X, Shi L. Adv. Mater. 2015; 27: 2101
      CrossrefPubMed
      14
    • 14a Neef CJ, Brotherston ID, Ferraris JP. Chem. Mater. 1999; 11: 1957
      CrossrefPubMed
    • 14b Pomerantz M, Gu X, Zhang SX. Macromolecules 2001; 34: 1817
      CrossrefPubMed
    • 14c Sotzing GA, Lee K. Macromolecules 2002; 35: 7281
      CrossrefPubMed
    • 14d Lee B, Seshadri V, Sotzing GA. Langmuir 2005; 21: 10797
      CrossrefPubMed
    • 14e Patra A, Wijsboom YH, Leitus G, Bendikov M. Chem. Mater. 2011; 23: 896
      CrossrefPubMed
    • 14f Yuan D, Liu L, Jiao X, Zou Y, McNeill CR, Xu W, Zhu X, Zhu D. Adv. Sci. 2018; 5: 1800947
      CrossrefPubMed
    • 14g Zhang C, Zang Y, Gann E, McNeill CR, Zhu X, Di CA, Zhu D. J. Am. Chem. Soc. 2014; 136: 16176
      CrossrefPubMed
    • 14h Ren L, Liu F, Shen X, Zhang C, Yi Y, Zhu X. J. Am. Chem. Soc. 2015; 137: 11294
      CrossrefPubMed
    • 14i Liu F, Zhou Z, Zhang C, Vergote T, Fan H, Liu F, Zhu X. J. Am. Chem. Soc. 2016; 138: 15523
      CrossrefPubMed
      15
    • 15a Liu F, Espejo GL, Qiu S, Oliva MM, Pina J, Seixas de Melo JS, Casado J, Zhu X. J. Am. Chem. Soc. 2015; 137: 10357
      CrossrefPubMed
    • 15b Mishra A, Ma CQ, Bäuerle P. Chem. Rev. 2009; 109: 1141
      CrossrefPubMed
    • 15c Zhang C, Zhu X. Acc. Chem. Res. 2017; 50: 1342
      CrossrefPubMed
    • 15d Yuan D. Chem 2019; 5: 744
      PubMed
    • 15e Yuan D, Huang D, Rivero SM, Carreras A, Zhang C, Zou Y, Jiao X, McNeill CR, Zhu X, Di CA, Zhu D, Casanova D, Casado J. Chem 2019; 5: 964
      CrossrefPubMed
    • 15f Ren L, Fan H, Huang D, Yuan D, Di CA, Zhu X. Chem. Eur. J. 2016; 22: 17136
      CrossrefPubMed
    • 15g Ren L, Yuan D, Gann E, Guo Y, Thomsen L, McNeill CR, Di CA, Yi Y, Zhu X, Zhu D. Chem. Mater. 2017; 29: 4999
      CrossrefPubMed
    • 15h Yuan D, Huang D, Zhang C, Zou Y, Di CA, Zhu X, Zhu D. ACS Appl. Mater. Interfaces 2017; 9: 28795
      CrossrefPubMed
    • 15i Ren L, Yuan D, Zhu X. Chem. Asian J. 2019; 14: 1717
      CrossrefPubMed
    • 15j Yuan D, Guo Y, Zeng Y, Fan Q, Wang J, Yi Y, Zhu X. Angew. Chem. Int. Ed. 2019; 58: 4958
      CrossrefPubMed
  • 16 Swager TM. Macromolecules 2017; 50: 4867
    CrossrefPubMed
  • 17 Synthesis of PT b T-Me:PSS: TbT-Me monomer, Fe2(SO4)3, and PSSH were added to a round-bottomed flask in deionized water (15 mg of TbT-Me in 1 mL of H2O) under ambient conditions. The mixture was vigorously stirred at room temperature in air for 2 days. The insoluble precipitate was leached by a filter membrane and a black solution was obtained as shown in Figure S1. The optimization details are shown in Figure S2
    CrossrefPubMed
  • 18 Aust RB, Bentley WH, Drickamer HG. J. Chem. Phys. 1964; 41: 1856
    CrossrefPubMed
  • 19 Park T, Park C, Kim B, Shin H, Kim E. Energy Environ. Sci. 2013; 6: 788
    CrossrefPubMed
  • 20 Fan Z, Li P, Du D, Ouyang J. Adv. Energy Mater. 2017; 7: 1602116
    CrossrefPubMed
  • 21 Kim YH, Sachse C, Machala ML, May C, Müller-Meskamp L, Leo K. Adv. Funct. Mater. 2011; 21: 1076
    CrossrefPubMed
  • 22 Bubnova O, Crispin X. Energy Environ. Sci. 2012; 5: 9345
    CrossrefPubMed
  • 23 Schwarze M, Gaul C, Scholz R, Bussolotti F, Hofacker A, Schellhammer KS, Nell B, Naab BD, Bao Z, Spoltore D, Vandewal K, Widmer J, Kera S, Ueno N, Ortmann F, Leo K. Nat. Mater. 2019; 18: 242
    CrossrefPubMed
  • 24 Bubnova O, Khan ZU, Malti A, Braun S, Fahlman M, Berggren M, Crispin X. Nat. Mater. 2011; 10: 429
    CrossrefPubMed
      • 25
    • 25a Poehler TO, Katz HE. Energy Environ. Sci. 2012; 5: 8110
      CrossrefPubMed
    • 25b Zhang Q, Sun Y, Xu W, Zhu D. Adv. Mater. 2014; 26: 6829
      CrossrefPubMed
    • 25c Russ B, Glaudell A, Urban JJ, Chabinyc ML, Segalman RA. Nat. Rev. Mater. 2016; 1: 16050
      CrossrefPubMed
    • 25d Sun Y, Di CA, Xu W, Zhu D. Adv. Electron. Mater. 2019; 5: 1800825
      CrossrefPubMed
    • 25e Zhang J, Song G, Qiu L, Feng Y, Chen J, Yan J, Liu L, Huang X, Cui Y, Sun Y, Xu W, Zhu D. Macromol. Rapid Commun. 2018; 39: 1800283
      CrossrefPubMed
    • 25f Kiefer D, Kroon R, Hofmann AI, Sun H, Liu X, Giovannitti A, Stegerer D, Cano A, Hynynen J, Yu L, Zhang Y, Nai D, Harrelson TF, Sommer M, Moule AJ, Kemerink M, Marder SR, McCulloch I, Fahlman M, Fabiano S, Müller C. Nat. Mater. 2019; 18: 149
      CrossrefPubMed
    • 25g Wu J, Sun Y, Pei WB, Huang L, Xu W, Zhang Q. Synth. Met. 2014; 196: 173
      CrossrefPubMed
    • 25h Yao CJ, Zhang HL, Zhang Q. Polymers 2019; 11: 107
      CrossrefPubMed
    • 25i Zeng YJ, Wu D, Cao XH, Zhou WX, Tang LM, Chen KQ. Adv. Funct. Mater. 2020; 30: 1903873
      CrossrefPubMed
    • 25j Lu Y, Wang J-Y, Pei J. Chem. Mater. 2019; 31: 6412
      CrossrefPubMed
    • 25k Kroon R, Mengistie DA, Kiefer D, Hynynen J, Ryan JD, Yu L, Müller C. Chem. Soc. Rev. 2016; 45: 6147
      CrossrefPubMed
    • 25l McGrail BT, Sehirlioglu A, Pentzer E. Angew. Chem. Int. Ed. 2015; 54: 1710
      CrossrefPubMed