

FOLLOWUS
International Sci. & Tech. Cooperation Base of Energy Materials and Application, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
czhang@zjut.edu.cn
Received:09 September 2020,
Revised:2020-10-24,
Accepted:02 November 2020,
Online First:25 November 2020,
Published:01 January 2021
Scan QR Code
Lv, X. J.; Xu, L. B.; Qian, L.; Yang, Y. Y.; Xu, Z. Y.; Li, J.; Zhang, C. A conjugated copolymer bearing imidazolium-based ionic liquid: electrochemical synthesis and electrochromic properties. Chinese J. Polym. Sci. 2021, 39, 537–544
Xiao-Jing Lv, Li-Bin Xu, Liang Qian, et al. A Conjugated Copolymer Bearing Imidazolium-based Ionic Liquid: Electrochemical Synthesis and Electrochromic Properties[J]. Chinese Journal of Polymer Science, 2021, 39(5): 537-544.
Lv, X. J.; Xu, L. B.; Qian, L.; Yang, Y. Y.; Xu, Z. Y.; Li, J.; Zhang, C. A conjugated copolymer bearing imidazolium-based ionic liquid: electrochemical synthesis and electrochromic properties. Chinese J. Polym. Sci. 2021, 39, 537–544 DOI: 10.1007/s10118-021-2525-z.
Xiao-Jing Lv, Li-Bin Xu, Liang Qian, et al. A Conjugated Copolymer Bearing Imidazolium-based Ionic Liquid: Electrochemical Synthesis and Electrochromic Properties[J]. Chinese Journal of Polymer Science, 2021, 39(5): 537-544. DOI: 10.1007/s10118-021-2525-z.
An imidazolium-based ionic liquid (IL) modified triphenylamine derivative
namely 1-(4-((4-(diphenylamino)benzoyl) oxy)butyl)-3-methyl imidazole tetrafluoroborate (TPAC
6
IL-BF
4
)
was designed and synthesized
and further applied with 3
4-ethylene dioxythiophene (EDOT) to prepare conjugated copolymer P(EDOT:TPAC
6
IL-BF
4
)
via
electrochemical polymerization. The cyclic voltammetry curves show that the copolymer P(EDOT:TPAC
6
IL-BF
4
) possesses two pairs of redox peaks
which should be ascribed to the redox behaviors of EDOT and triphenylamine. The ultraviolet-visible (UV-Vis) absorption spectrum of P(EDOT:TPAC
6
IL-BF
4
) exhibits one maximum absorption peak at 580 nm and a small shoulder characteristic peak at 385 nm under neutral state which are assigned to
π
-
π
*
conjugated structure of EDOT and triphenylamine. After being applied at the positive voltage
the copolymer color changes from dark blue to light blue
which is close to the color of poly(3
4-ethylenedioxythiophene) (PEDOT). Surprisingly
the copolymer P(EDOT:TPAC
6
IL-BF
4
) shows shorter switching time of 0.37 s
0.30 s at 580 nm and 0.38 s
0.45 s at 1100 nm compared with PEDOT. It is more intriguing that the copolymer P(EDOT:TPAC
6
IL-BF
4
) exhibits electrochromism even in free supporting electrolyte. The results confirm that the existence of imidazolium-based ionic liquid has an improvement on the ion diffusion properties and the switching time of conjugated polymer
which may provide a potential direction for the preparation of high-performance electrochromic materials.
Macher, S.; Schott, M.; Sassi, M.; Facchinetti, I.; Ruffo, R.; Patriarca, G.; Beverina, L.; Posset, U.; Giffin, G. A. Löbmann P. . New roll-to-roll processable PEDOT-based polymer with colorless bleached state for flexible electrochromic devices . Adv. Funct. Mater. , 2020 . 30 1906254 DOI: 10.1002/adfm.201906254 http://doi.org/10.1002/adfm.201906254 .
Wang, Z.; Wang, X. Y.; Cong, S.; Chen, J.; Sun, H. Z.; Chen, Z. G.; Song, G.; Geng, F. X.; Chen, Q.; Zhao, Z. G. . Towards full-colour tunability of inorganic electrochromic devices using ultracompact fabry-perot nanocavities . Nat. Commun. , 2020 . 11 302 DOI: 10.1038/s41467-019-14194-y http://doi.org/10.1038/s41467-019-14194-y .
Kim, J.; Rémond, M.; Kim, D.; Jang, H.; Kim, E. . Electrochromic conjugated polymers for multifunctional smart windows with integrative functionalities . Adv. Mater. Technol. , 2020 . 5 1900890 DOI: 10.1002/admt.201900890 http://doi.org/10.1002/admt.201900890 .
Yen, H. J.; Chen, C. J.; Liou, G. S. . Flexible multi-colored eectrochromic and volatile polymer memory devices derived from starburst triarylamine-based electroactive polyimide . Adv. Funct. Mater. , 2013 . 23 5307 - 5316 . DOI: 10.1002/adfm.201300569 http://doi.org/10.1002/adfm.201300569 .
Lv, X. J.; Li, W. J.; Ouyang, M.; Zhang, Y. J.; Wright, D. S.; Zhang, C. . Polymeric electrochromic materials with donor-acceptor structures . J. Mater. Chem. C , 2017 . 5 12 - 28 . DOI: 10.1039/C6TC04002K http://doi.org/10.1039/C6TC04002K .
Han, Y. T.; Xing, Z.; Ma, P. Y.; Li, S.; Wang, C.; Jiang, Z. H.; Zhang,. C. . Design rules for improving the cycling stability of high-performance donor-acceptor-type electrochromic polymers . ACS Appl. Mater. Interfaces , 2020 . 12 7529 - 7538 . DOI: 10.1021/acsami.9b19214 http://doi.org/10.1021/acsami.9b19214 .
Ji, L. L.; Dai, Y. Y.; Yan, S. M.; Lv, X. J.; Su, C.; Xu, L. H.; Lv, Y. K.; Ouyang, M.; Chen, Z. F.; Zhang, C. . A fast electrochromic polymer based on TEMPO substituted polytriphenylamine . Sci. Rep. , 2016 . 6 30068 DOI: 10.1038/srep30068 http://doi.org/10.1038/srep30068 .
Ming, S. L.; Li, Z. y.; Zhen, S. J.; Liu, P. P.; Jiang, F. G.; Nie, G. M.; Xu, J. K. . High-performance D-A-D type electrochromic polymer with π spacer applied in supercapacitor . Chem. Eng. J. , 2020 . 390 124572 DOI: 10.1016/j.cej.2020.124572 http://doi.org/10.1016/j.cej.2020.124572 .
Guo, Q. F.; Li, J. J.; Zhang, B.; Nie, G. M.; Wang, D. B. . High-performance asymmetric electrochromic-supercapacitor device based on poly(indole-6-carboxylicacid)/TiO 2 nanocom-posites . Appl. Mater. Interfaces , 2019 . 11 6491 - 6501 . DOI: 10.1021/acsami.8b19505 http://doi.org/10.1021/acsami.8b19505 .
Lv, X. J.; Yan, S. M.; Dai, Y. Y.; Ouyang, M.; Yang, Y.; Yu, P. F.; Zhang, C. . Ion diffusion and electrochromic performance of poly(4,4′,4″-tris[4-(2-bithienyl)phenyl]amine) based on ionic liquid as electrolyte . Electrochim. Acta , 2015 . 186 85 - 94 . DOI: 10.1016/j.electacta.2015.10.127 http://doi.org/10.1016/j.electacta.2015.10.127 .
Gaupp, C. L.; Welsh, D. M.; Reynolds, J. R. . Poly(ProDOT-Et 2 ): a high-contrast, high-coloration efficiency electrochromic polymer . Macromolecules , 2002 . 23 885 - 889 . .
Argun, A. A.; Aubert, P. H.; Thompson, B. C.; Schwendeman, I.; Gaupp, C. L.; Hwang, J.; Pinto, N. J.; Tanner, D. B. MacDiarmid, A. G.; Reynolds, J. R. . Multicolored electrochromism in polymers: structures and devices . Chem. Mater. , 2004 . 16 4401 - 4412 . DOI: 10.1021/cm049669l http://doi.org/10.1021/cm049669l .
Colak, B.; Büyükkoyuncu, A.; Koyuncu, F. B.; Koyuncu, S. . Electrochromic properties of phenantrene centered EDOT polymers . Polymer , 2017 . 123 366 - 375 . DOI: 10.1016/j.polymer.2017.07.035 http://doi.org/10.1016/j.polymer.2017.07.035 .
Hacioglu, S. O. . Copolymerization of azobenzene-bearing monomer and 3,4-ethylenedioxythiophene (EDOT): improved electrochemical performance for electrochromic device appli-cations . Chinese J. Polym. Sci. , 2020 . 38 109 - 117 . DOI: 10.1007/s10118-019-2306-0 http://doi.org/10.1007/s10118-019-2306-0 .
Chen, H. W.; Li, C. . PEDOT: fundamentals and its nanocomposites for energy storage . Chinese J. Polym. Sci. , 2020 . 38 435 - 448 . DOI: 10.1007/s10118-020-2373-2 http://doi.org/10.1007/s10118-020-2373-2 .
Guo, Q. F.; Zhao, X. Q.; Li, Z. Y.; Wang, B. Y.; Wang, D. B.; Nie, G. M. . High performance multicolor intelligent supercapacitor and its quantitative monitoring of energy storage level by electrochromic parameters . Appl. Energy Mater. , 2020 . 3 2727 - 2736 . DOI: 10.1021/acsaem.9b02392 http://doi.org/10.1021/acsaem.9b02392 .
Ming, S. L.; Lin, K. W.; Zhang, H.; Jiang, F. X.; Liu, P. P.; Xu, J. K.; Nie, G. M.; Duan, X. M. . Electrochromic polymers with multiple redox couples applied to monitor energy storage states of supercapacitors . Chem. Commun. , 2020 . 56 5275 - 5278 . DOI: 10.1039/D0CC00690D http://doi.org/10.1039/D0CC00690D .
Arias-Pardilla, J.; Giménez-Gómez, P. A.; Peña, A.; Segura, J. L.; Otero, T. F. . Synthesis, electropolymerization and characterization of a cross-linked PEDOT derivative . J. Mater. Chem. , 2012 . 22 4944 - 4952 . DOI: 10.1039/c2jm14909e http://doi.org/10.1039/c2jm14909e .
Hu, B.; Li, C. Y.; Liu, Z. C.; Zhang, X. L.; Luo, W.; Jin, L. . Synthesis and multi-electrochromic properties of asymmetric structure polymers based on carbazole-EDOT and 2,5-dithienylpyrrole derivatives . Electrochim. Acta , 2019 . 305 1 - 10 . DOI: 10.1016/j.electacta.2019.03.050 http://doi.org/10.1016/j.electacta.2019.03.050 .
Cheng, X. F.; Zhao, J. S.; Cui, C. S.; Fu, Y. Z.; Zhang, X. X. . Star-shaped conjugated systems derived from thienyl-derivatized poly(triphenylamine)s as active materials for electrochromic devices . J. Electroanal. Chem. , 2012 . 677-680 24 - 30 . DOI: 10.1016/j.jelechem.2012.04.017 http://doi.org/10.1016/j.jelechem.2012.04.017 .
Zhen, S. J.; Xu, J. K.; Lu, B. Y.; Zhang, S. M.; Zhao, L.; Li, J. . Tuning the optoelectronic properties of polyfuran by design of furan-EDOT monomers and free-standing films with enhanced redox stability and electrochromic performances . Electrochim. Acta , 2014 . 146 666 - 678 . DOI: 10.1016/j.electacta.2014.09.034 http://doi.org/10.1016/j.electacta.2014.09.034 .
Liu, F. H.; Bai, J.; Yu, G.; Ma, F. H.; Hou, Y. J.; Niu, H. J. . Synthesis, electrochromic properties and flash memory behaviors of novel D-A-D polyazomethines containing EDOT and thiophene units . Org. Electron. , 2020 . 77 105538 DOI: 10.1016/j.orgel.2019.105538 http://doi.org/10.1016/j.orgel.2019.105538 .
Wang, B. S.; Qin, L.; Mu, T. C.; Xue, Z. M; Gao, G. H. . Are ionic liquids chemically stable? . Chem. Rev. , 2017 . 117 7113 - 7131 . DOI: 10.1021/acs.chemrev.6b00594 http://doi.org/10.1021/acs.chemrev.6b00594 .
Maruyama, S.; Prastiawan, I. B. H.; Toyabe, K.; Higuchi, Y.; Koganezawa, T.; Kubo, M.; Matsumoto, Y. . Ionic conductivity in ionic liquid nano thin films . ACS Nano , 2018 . 12 10509 - 10517 . DOI: 10.1021/acsnano.8b06386 http://doi.org/10.1021/acsnano.8b06386 .
Xiao, W. C.; Yang, Q.; Zhu, S. L. . Comparing ion transport in ionic liquids and polymerized ionic liquids . Sci. Rep. , 2020 . 10 7825 DOI: 10.1038/s41598-020-64689-8 http://doi.org/10.1038/s41598-020-64689-8 .
Ouyang, M.; Yang, Y.; Lv, X. J.; Han, Y. G.; Huang, S. B.; Dai, Y. Y.; Su, C.; Lv, Y. K.; Sumita, M.; Zhang, C. . Enhanced electrochromic switching speed and electrochemical stability of conducting polymer film on an ionic liquid functionalized ITO electrode . New J. Chem. , 2015 . 39 5329 - 5335 . DOI: 10.1039/C5NJ00703H http://doi.org/10.1039/C5NJ00703H .
Qian, L.; Lv, X. J.; Ouyang, M.; Tameev, A.; Katin, K.; Maslov, M.; Bi, Q.; Huang, C. H.; Zhu, R.; Zhang, C. . Fast switching properties and ion diffusion behavior of polytriphenylamine derivative with pendent ionic liquid unit . ACS Appl. Mater. Interfaces , 2018 . 10 32404 - 32412 . DOI: 10.1021/acsami.8b09878 http://doi.org/10.1021/acsami.8b09878 .
Lo, C. K.; Shen, D. E.; Reynolds, J. R. . Fine-tuning the color hue of π -conjugated black-to-clear electrochromic random copolymers . Macromolecules , 2019 . 52 6773 - 6779 . DOI: 10.1021/acs.macromol.9b01443 http://doi.org/10.1021/acs.macromol.9b01443 .
Gaupp, C. L.; Reynolds, J. R. . Multichromic copolymers based on 3,6-bis(2-(3,4-ethylenedioxythiophene))- N -alkylcarbazole derivatives . Macromolecules , 2003 . 36 6305 - 6315 . DOI: 10.1021/ma034493e http://doi.org/10.1021/ma034493e .
Lv, X. J.; Huang, C. H.; Tameev, A.; Qian, L.; Zhu R.; Katin, K.; Maslov, M.;. Nekrasov, A; Zhang, C. . Electrochemical polymeri-zation process and excellent electrochromic properties of fer-rocene-functionalized polytriphenylamine derivative . Dyes Pigment , 2019 . 163 433 - 440 . DOI: 10.1016/j.dyepig.2018.12.019 http://doi.org/10.1016/j.dyepig.2018.12.019 .
Zhang, C.; Hua, C.; Wang, G. H.; Ouyang, M.; Ma, C. A. . A novel multichromic copolymer via electrochemical copolymerization of ( S )-1,1′-binaphthyl-2,2′-diyl bis( N -(6-hexanoic acid-1-yl) pyrrole) and 3,4-ethylenedioxythiophene . Electrochim. Acta , 2010 . 55 4103 - 4111 . DOI: 10.1016/j.electacta.2010.02.086 http://doi.org/10.1016/j.electacta.2010.02.086 .
Dai, Y. Y.; Li, W. J.; Qu, X. X.; Liu, J.; Yan, S. M.; Ouyang, M.; Lv, X. J.; Zhang C. . Electrochemistry, electrochromic and color memory properties of polymer/copolymer based on novel dithienylpyrrole structure . Electrochima. Acta , 2017 . 229 271 - 280 . DOI: 10.1016/j.electacta.2017.01.156 http://doi.org/10.1016/j.electacta.2017.01.156 .
Lv, X. J.; Zha, L.X.; Qian, L.; Xu, X. J.; Bi, Q.; Xu, Z. Y.; Wright, D. S.; Zhang, C. . Controllable fabrication of perylene bisimide self-assembled film and patterned all-solid-state electrochromic device . Chem. Eng. J. , 2020 . 386 123939 DOI: 10.1016/j.cej.2019.123939 http://doi.org/10.1016/j.cej.2019.123939 .
Lv, X. J.; Bi, Q.; Tameev, A.; Zhang, Y. J.; Qian L.; Ouyang, M.; Zhang, C. . A new green-to-transmissive polymer with electroactive poly(3,4-ethylene dioxythiophene): poly(styrene sulfonate) as an interface layer for achieving high-performance electrochromic device . J. Polym. Sci. , 2020 . 58 937 - 947 . DOI: 10.1002/pol.20190284 http://doi.org/10.1002/pol.20190284 .
0
Views
119
Downloads
1
CSCD
Publicity Resources
Related Articles
Related Author
Related Institution
京公网安备11010802046900号