Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications

Serife O. Hacioglu

doi:10.1007/s10118-019-2306-0

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Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications

ARTICLE | Updated：2019-09-04

- Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications
- Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications
- Chinese Journal of Polymer Science 2020年38卷第2期页码：109-117
- Affiliations：
  
  Iskenderun Technical University, Department of Engineering Science, 31200, Hatay, Turkey
- Author bio：
  
  serife.hacioglu@iste.edu.tr
- Funds：
  
  I would like to thank and appreciate Prof. Dr. Levent Toppare (Department of Chemistry, Middle East Technical University, Turkey) for his guidance and support for my academic carrier.
- DOI：10.1007/s10118-019-2306-0
  中图分类号：
- 收稿：2019-04-30，
  
  修回：2019-5-20，
  
  录用：2019-5-25，
  
  网络首发：2019-09-04，
  
  纸质出版：2020-02
- Accepted：
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Hacioglu, S. O. Copolymerization of azobenzene-bearing monomer and 3,4-ethylenedioxythiophene (EDOT): improved electrochemical performance for electrochromic device applications. Chinese J. Polym. Sci. 2020, 38, 109–117.

Serife O. Hacioglu. Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications[J]. Chinese Journal of Polymer Science, 2020, 38(2): 109-117.
Hacioglu, S. O. Copolymerization of azobenzene-bearing monomer and 3,4-ethylenedioxythiophene (EDOT): improved electrochemical performance for electrochromic device applications. Chinese J. Polym. Sci. 2020, 38, 109–117. DOI： 10.1007/s10118-019-2306-0.

Serife O. Hacioglu. Copolymerization of Azobenzene-bearing Monomer and 3,4-Ethylenedioxythiophene (EDOT): Improved Electrochemical Performance for Electrochromic Device Applications[J]. Chinese Journal of Polymer Science, 2020, 38(2): 109-117. DOI： 10.1007/s10118-019-2306-0.

摘要

Abstract

In this study

novel electrochromic copolymers of 3

4-ethylenedioxythiophene (EDOT) and (

)-1

2-bis(2-fluoro-4-(4-hexylthiophen-2-yl)phenyl)diazene (M1) with different monomer feed ratios were designed and synthesized electrochemically. Electrochemical and spectroelectrochemical characterizations were performed using voltammetry and UV-Vis-NIR spectrophotometry techniques to test the applicability of copolymers for electrochromic applications. In terms of electrochemical behaviors

addition of an electron-rich EDOT unit into the azobenzene-containing copolymer increased the electron density on the polymer chain and afforded copolymers with very low oxidation potentials at around 0.30 V. While the homopolymers (P1 and PEDOT) exhibited neutral state absorptions centered at 510 and 583 nm

EDOT-bearing copolymers showed red shifted absorptions compared to those of P1 with narrower optical band gaps. In addition

the poor optical contrast and switching times of azobenzene-bearing homopolymer were significantly improved with EDOT addition into the copolymer chain. As a result of the promising electrochromic and kinetic preperties

CoP1.5-bearing single layer electrochromic device that works between purple and light greenish blue colors was constructed and characterized.

关键词

Keywords

references

Cheng, X.; Fu, Y.; Zhao, J.; Zhang, Y . Polyaniline with high crystallinity degree: synthesis, structure, and electrochemical properties . J. Appl. Polym. Sci. , 2014 . 131 39770 - 39777 . .

Cansu-Ergun, E. G . Covering the more visible region by electrochemical copolymerization of carbazole and benzothiadiazole based donor-acceptor type monomers . Chinese J. Polym. Sci. , 2019 . 37 28 - 35 . DOI: 10.1007/s10118-019-2181-8 http://doi.org/10.1007/s10118-019-2181-8 .

Guo, B.; Li, W.; Guo, X.; Meng, X.; Ma, W.; Zhang, M.; Li, Y . High efficiency nonfullerene polymer solar cells with thick active layer and large area . Adv. Mater. , 2017 . 29 1702291 - 1702297 . DOI: 10.1002/adma.201702291 http://doi.org/10.1002/adma.201702291 .

Azeri, O.; Aktas, E.; Istanbulluoglu, C.; Hacioglu, S. O.; Cevher, S. C.; Toppare, L.; Cirpan, A . Efficient benzodithiophene and thienopyrroledione containing random polymers as components for organic solar cells . Polymer , 2017 . 133 60 - 67 . DOI: 10.1016/j.polymer.2017.11.024 http://doi.org/10.1016/j.polymer.2017.11.024 .

Kamtekar, K. J.; Vaughan, H. L.; Lyons, B. P.; Monkman, A. P.; Pandya, S. U.; Bryce, M. R . Synthesis and spectroscopy of poly(9,9-dioctylfluorene-2,7-diyl- co -2,8-dihexyldibenzothiophene- S , S -dioxide-3,7-diyl)s: solution-processable, deep-blue emitters with a high triplet energy . Macromolecules, , 2010 . 43 4481 - 4488 . DOI: 10.1021/ma100566p http://doi.org/10.1021/ma100566p .

Lee, K.; Povlich, L. K.; Kim, J . Recent advances in fluorescent and colorimetric conjugated polymer-based biosensors . Analyst , 2010 . 135 2179 - 2189 . DOI: 10.1039/c0an00239a http://doi.org/10.1039/c0an00239a .

Soylemez, S.; Hacioglu, S. O.; Kesik, M.; Unay, H.; Cirpan, A.; Toppare, L . A novel and effective surface design: conducting polymer/ β -cyclodextrin host-guest system for cholesterol biosensor . ACS Appl. Mater. Interfaces , 2014 . 6 18290 - 18300 . DOI: 10.1021/am5054493 http://doi.org/10.1021/am5054493 .

Thompson, B. C.; Schottland, P.; Zong, K.; Reynolds, J. R . In situ colorimetric analysis of electrochromic polymers and devices . Chem. Mater. , 2000 . 12 1563 - 1571 . DOI: 10.1021/cm000097o http://doi.org/10.1021/cm000097o .

Sapp, S. A.; Sotzing, G. A.; Reynolds, J. R . High contrast ratio and fast-switching dual polymer electrochromic devices . Chem. Mater. , 1998 . 10 2101 - 2108 . DOI: 10.1021/cm9801237 http://doi.org/10.1021/cm9801237 .

Yoo, S. J.; Cho, J. H.; Lim, J. W.; Park, S. H.; Jang, J.; Sung, Y. E . High contrast ratio and fast switching polymeric electrochromic films based on water-dispersible polyaniline-poly(4-styrenesulfonate) nanoparticles . Electrochem. Commun. , 2010 . 12 164 - 167 . DOI: 10.1016/j.elecom.2009.11.014 http://doi.org/10.1016/j.elecom.2009.11.014 .

Sonmez, G.; Sonmez, H. B.; Shen, C. K. F.; Jost, R. W.; Rubin, Y.; Wudl, F . A processable green polymeric electrochromic . Macromolecules , 2005 . 38 669 - 675 . DOI: 10.1021/ma0484173 http://doi.org/10.1021/ma0484173 .

Roncali, J . Molecular engineering of the band gap of π -conjugated systems: facing technological applications . Macromol. Rapid Commun. , 2007 . 28 1761 - 1775 . DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

Gunbas, G.; Toppare, L . Green as it gets; donor-acceptor type polymers as the key to realization of RGB based polymer display devices . Macromol. Symp. , 2010 . 297 79 - 86 . DOI: 10.1002/masy.v297.1 http://doi.org/10.1002/masy.v297.1 .

Nie, G.; Qu, L.; Xu, J . Electrosyntheses and characterizations of a new soluble conducting copolymer of 5-cyanoindole and 3,4-ethylenedioxythiophene . Electrochim. Acta , 2008 . 53 8351 - 8358 . DOI: 10.1016/j.electacta.2008.06.058 http://doi.org/10.1016/j.electacta.2008.06.058 .

Han, R.; Lu, S.; Wang, Y.; Zhang, X.; Wu, Q.; He, T . Influence of monomer concentration during polymerization on performance and catalytic mechanism of resultant poly(3,4-ethylenedioxythiophene) counter electrodes for dye-sensitized solar cells . Electrochim. Acta , 2015 . 173 796 - 803 . .

Wang, Z.; Xu, J.; Lu, B.; Zhang, S.; Qin, L.; Mo, D.; Zhen, S . Poly(thieno[3,4- b ]-1,4-oxathiane): medium effect on electropolymerization and electrochromic performance . Langmuir , 2014 . 30 15581 - 15589 . DOI: 10.1021/la503948f http://doi.org/10.1021/la503948f .

Liu, X.; Hu, Y.; Shen, L.; Zhang, G.; Cao, T.; Xu, J.; Zhao, F.; Hou, J.; Liu, H.; Jiang, F . Novel copolymers based on PEO bridged thiophenes and 3,4-ethylenedioxythiophene: electrochemical, optical, and electrochromic properties . Electrochim. Acta , 2018 . 288 52 - 60 . DOI: 10.1016/j.electacta.2018.08.072 http://doi.org/10.1016/j.electacta.2018.08.072 .

Hu, Y.; Jiang, F.; Lu, B.; Liu, C.; Hou, J.; Xu, J . Free-standing oligo(oxyethylene)-functionalized polythiophene withthe 3,4-ethylenedioxythiophene building block: electrosynthesis, electrochromic and thermoelectric properties . Electrochim. Acta , 2017 . 228 361 - 370 . DOI: 10.1016/j.electacta.2017.01.019 http://doi.org/10.1016/j.electacta.2017.01.019 .

Hu, Y.; Wang, Z.; Lin, K.; Xu, J.; Duan, X.; Zhao, F.; Hou, J.; Jiang, F . Electrosynthesis and electrochromic properties of free-standing copolymer based on oligo(oxyethylene) cross-linked 2,2′-bithiophene and 3,4-ethylenedioxythiophene . J. Polym. Sci., Part A: Polym. Chem. , 2016 . 54 1583 - 1592 . DOI: 10.1002/pola.v54.11 http://doi.org/10.1002/pola.v54.11 .

He, L.; Freeman, H. S.; Nakpathom, M.; Boyle, P. D . Synthesis and X-ray analysis of a perfluoroalkyl-substituted azobenzene dye . Dyes Pigments , 2015 . 120 245 - 250 . DOI: 10.1016/j.dyepig.2015.04.014 http://doi.org/10.1016/j.dyepig.2015.04.014 .

Gong, C. B.; He, L. H.; Long, J. F.; Liu, L. T.; Liu, S.; Tang, Q.; Fu, X. K . Synthesis and characterisation of azobenzene-bridged cationic-cationic and neutral-cationic electrochromic materials . Synthetic Met. , 2016 . 220 147 - 154 . DOI: 10.1016/j.synthmet.2016.06.011 http://doi.org/10.1016/j.synthmet.2016.06.011 .

Ferreira, J.; Santos, M. J. L.; Matos, R.; Ferreira, O. P.; Rubira, A. F.; Girotto, E. M . Structural and electrochromic study of polypyrrole synthesized with azo and anthraquinone dyes . J. Electroanal. Chem. , 2006 . 591 27 - 32 . DOI: 10.1016/j.jelechem.2006.03.016 http://doi.org/10.1016/j.jelechem.2006.03.016 .

Pei, X.; Fernandes, A.; Mathy, B.; Laloyaux, X.; Nysten, B.; Riant, O.; Jonas, A. M . Correlation between the structure and wettability of photoswitchable hydrophilic azobenzene monolayers on silicon . Langmuir , 2011 . 27 9403 - 9412 . DOI: 10.1021/la201526u http://doi.org/10.1021/la201526u .

Apaydin, D. H.; Akpinar, H.; Sendur, M.; Toppare, L . Electrochromism in multichromic conjugated polymers: thiophene and azobenzene derivatives on the main chain . J. Electroanal. Chem. , 2012 . 665 52 - 57 . DOI: 10.1016/j.jelechem.2011.11.016 http://doi.org/10.1016/j.jelechem.2011.11.016 .

Yigit, D.; Udum, Y. A.; Güllü, M.; Toppare, L . Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: multicolored electrochromic polymers . J. Electroanal. Chem. , 2014 . 712 215 - 222 . DOI: 10.1016/j.jelechem.2013.11.028 http://doi.org/10.1016/j.jelechem.2013.11.028 .

Yagmur, I.; Ak, M.; Bayrakceken, A . Fabricating multicolored electrochromic devices using conducting copolymers . Smart Mater. Struct. , 2013 . 22 115022 - 115030 . DOI: 10.1088/0964-1726/22/11/115022 http://doi.org/10.1088/0964-1726/22/11/115022 .

Soganci, T.; Kurtay, G.; Ak, M.; Güllü, M . Preparation of an EDOT-based polymer: optoelectronic properties and electrochromic device application . RSC Adv. , 2014 . 5 2630 - 2639 . .

De Paoli, M. A.; Gazotti, W. A . Electrochemistry, polymers and opto-electronic devices: a combination with a future . J. Braz. Chem. Soc. , 2002 . 13 410 - 424 . .

Camurlu P.; Gultekin, C . A comprehensive study on utilization of N-substituted poly(2,5-dithienylpyrrole) derivatives in electrochromic devices . Sol. Energy Mater. Sol. Cells , 2012 . 107 142 - 147 . DOI: 10.1016/j.solmat.2012.07.031 http://doi.org/10.1016/j.solmat.2012.07.031 .

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