A novel quinoxaline-based donor-acceptor type electrochromic polymer

Ji Young Lee; Song-Yi Han; Bogyu Lim; Yoon-Chae Nah

Journal of Industrial and Engineering Chemistry, Vol.70, 380-384, February, 2019

DOI10.1016/j.jiec.2018.10.039 Export Citation

A novel quinoxaline-based donor-acceptor type electrochromic polymer

Ji Young Lee, Song-Yi Han¹, Bogyu Lim^†, and Yoon-Chae Nah^{1, †}

Future Technology Research Center, Corporate R&D, LG Chem/LG Science Park, 30, Magokjungang 10-ro, Gangseo-gu, Seoul, 07796, Republic of Korea
¹IPCE, School of Energy, Materials, and Chemical Engineering, Korea University of Technology and Education, 1600 Chungjeol-ro, Cheonan, Chungnam, 31253, Republic of Korea

E-mail:,

We synthesize a quinoxaline-based novel conjugated donor.acceptor random copolymer containing benzodithiophene and 2,5-difluorophenylenedithiophene units as electron donors (coded r-PQ) and investigate the electrochromic properties of the material. Despite its high molecular weight, r-PQ is highly soluble in organic solvents owing to the side chain of alkoxy at the meta-position of the phenyl ring. The r-PQ film exhibits excellent redox-promoted blue to transmissive-state color switching with high coloration efficiency (>250 cm2/C) and a fast response time (<0.5 s). These results suggest that our quinoxaline-based random copolymer could be a promising candidate as an organic electrochromic material.

Keywords:Electrochromic;Quinoxaline;Donor-acceptor type;Random polymer;Non-covalent interaction

[References]

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Araki S, Nakamura K, Kobayashi K, Tsuboi A, Kobayashi N, Adv. Mater., 24, OP122 (2012)
Kim HN, Cho SM, Ah CS, Song J, Ryu H, Kim YH, Kim TY, Mater. Res. Bull., 82, 16 (2016)
Bach U, Corr D, Lupo D, Pichot F, Ryan M, Adv. Mater., 14(11), 845 (2002)
Weng W, Higuchi T, Suzuki M, Fukuoka T, Shimomura T, Ono M, Radhakrishnan L, Wang H, Suzuki N, Oveisi H, Yamauchi Y, Angew. Chem.-Int. Edit., 49, 3956 (2010)
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Nah YC, Ghicov A, Kim D, Berger S, Schmuki P, J. Am. Chem. Soc., 130(48), 16154 (2008)
Wen RT, Granqvist CG, Niklasson GA, Adv. Funct. Mater., 25(22), 3359 (2015)
Beaujuge PM, Ellinger S, Reynolds JR, Nat. Mater., 7(10), 795 (2008)
Sun XW, Wang JX, Nano Lett., 8, 1884 (2008)
Sondergaard RR, Hosel M, Krebs FC, J. Polym. Sci. B: Polym. Phys., 51(1), 16 (2013)
Dyer AL, Thompson EJ, Reynolds JR, ACS Appl. Mater. Interfaces, 3, 1787 (2011)
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Iqbal S, Ahmad S, J. Ind. Eng. Chem., 60, 53 (2018)
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Hwang KH, Kim DH, Choi MH, Han JP, Moon DK, J. Ind. Eng. Chem., 34, 66 (2016)
Joo CW, Cho HS, Kwon BH, Cho NS, Kim YH, Kim YH, Lee JH, J. Ind. Eng. Chem., 65, 35 (2018)
Lande M, Navgire M, Rathod S, Katkar S, Yelwande A, Arbad B, J. Ind. Eng. Chem., 18(1), 277 (2012)
Steckler TT, Henriksson P, Mollinger S, Lundin A, Salleo A, Andersson MR, J. Am. Chem. Soc., 136(4), 1190 (2014)
Cevher SC, Hizalan G, Temiz C, Udum YA, Toppare L, Cirpan A, Polymer, 101, 208 (2016)
Kim BG, Jeong EJ, Chung JW, Seo S, Koo B, Kim JS, Nat. Mater., 12(7), 659 (2013)
Gao X, Shen J, Hu B, Tu G, Macromol. Chem. Phys., 215, 1388 (2014)
Wang E, Bergqvist J, Vandewal K, Ma Z, Hou L, Lundin A, Himmelberger S, Salleo A, Muller C, Inganas O, Zhang F, Andersson MR, Adv. Eng. Mater., 3, 806 (2013)
Lee YS, Lee JY, Bang SM, Lim B, Lee J, Na SI, J. Mater. Chem. A, 4, 11439 (2016)
Kim T, Lee JY, Heo J, Lim B, Kim JY, Polym. Chem., 9, 1216 (2018)
Kong L, Wang M, Ju X, Zhao J, Zhang Y, Xie Y, Polymers, 9, 656 (2017)
Tao YJ, Zhang K, Zhang ZY, Cheng HF, J. Electroanal. Chem., 769, 80 (2016)
Chen S, Zhang D, Wang M, Kong L, Zhao J, New J. Chem., 40, 2178 (2016)
Wang C, Wang M, Zhang Y, Zhao J, Fu C, RSC Adv., 6, 80002 (2016)
Kavak E, Us CN, Yavuz E, Kivrak A, Ozkut MI, Electrochim. Acta, 182, 537 (2015)
Liu Y, Wang M, Zhao J, Cui C, Liu J, RSC Adv., 4, 52712 (2014)

[Referenced By]

[1] Deb SK, Appl. Opt., 8, 192 (1969)

[2] Niklasson GA, Granqvist CG, J. Mater. Chem., 17, 127 (2007)

[3] Baetens R, Jelle BP, Gustavsen A, Sol. Energy Mater. Sol. Cells, 94, 87 (2010)

[4] Wang Y, Runnerstrom EL, Milliron DJ, Annu. Rev. Chem. Biomol. Eng., 7, 283 (2016)

[5] Araki S, Nakamura K, Kobayashi K, Tsuboi A, Kobayashi N, Adv. Mater., 24, OP122 (2012)

[6] Kim HN, Cho SM, Ah CS, Song J, Ryu H, Kim YH, Kim TY, Mater. Res. Bull., 82, 16 (2016)

[7] Bach U, Corr D, Lupo D, Pichot F, Ryan M, Adv. Mater., 14(11), 845 (2002)

[8] Weng W, Higuchi T, Suzuki M, Fukuoka T, Shimomura T, Ono M, Radhakrishnan L, Wang H, Suzuki N, Oveisi H, Yamauchi Y, Angew. Chem.-Int. Edit., 49, 3956 (2010)

[9] Moon HC, Lodge TP, Frisbie CD, Chem. Mater., 27, 1420 (2015)

[10] Nah YC, Ghicov A, Kim D, Berger S, Schmuki P, J. Am. Chem. Soc., 130(48), 16154 (2008)

[11] Wen RT, Granqvist CG, Niklasson GA, Adv. Funct. Mater., 25(22), 3359 (2015)

[12] Beaujuge PM, Ellinger S, Reynolds JR, Nat. Mater., 7(10), 795 (2008)

[13] Sun XW, Wang JX, Nano Lett., 8, 1884 (2008)

[14] Sondergaard RR, Hosel M, Krebs FC, J. Polym. Sci. B: Polym. Phys., 51(1), 16 (2013)

[15] Dyer AL, Thompson EJ, Reynolds JR, ACS Appl. Mater. Interfaces, 3, 1787 (2011)

[16] Beaujuge PM, Reynolds JR, Chem. Rev., 110(1), 268 (2010)

[17] Iqbal S, Ahmad S, J. Ind. Eng. Chem., 60, 53 (2018)

[18] Wang E, Bergqvist J, Vandewal K, Ma Z, Hou L, Lundin A, Himmelberger S, Salleo A, Muller C, Inganas O, Zhang F, Andersson MR, Adv. Eng. Mater., 3, 806 (2013)

[19] Hwang KH, Kim DH, Choi MH, Han JP, Moon DK, J. Ind. Eng. Chem., 34, 66 (2016)

[20] Joo CW, Cho HS, Kwon BH, Cho NS, Kim YH, Kim YH, Lee JH, J. Ind. Eng. Chem., 65, 35 (2018)

[21] Lande M, Navgire M, Rathod S, Katkar S, Yelwande A, Arbad B, J. Ind. Eng. Chem., 18(1), 277 (2012)

[22] Steckler TT, Henriksson P, Mollinger S, Lundin A, Salleo A, Andersson MR, J. Am. Chem. Soc., 136(4), 1190 (2014)

[23] Cevher SC, Hizalan G, Temiz C, Udum YA, Toppare L, Cirpan A, Polymer, 101, 208 (2016)

[24] Kim BG, Jeong EJ, Chung JW, Seo S, Koo B, Kim JS, Nat. Mater., 12(7), 659 (2013)

[25] Gao X, Shen J, Hu B, Tu G, Macromol. Chem. Phys., 215, 1388 (2014)

[26] Wang E, Bergqvist J, Vandewal K, Ma Z, Hou L, Lundin A, Himmelberger S, Salleo A, Muller C, Inganas O, Zhang F, Andersson MR, Adv. Eng. Mater., 3, 806 (2013)

[27] Lee YS, Lee JY, Bang SM, Lim B, Lee J, Na SI, J. Mater. Chem. A, 4, 11439 (2016)

[28] Kim T, Lee JY, Heo J, Lim B, Kim JY, Polym. Chem., 9, 1216 (2018)

[29] Kong L, Wang M, Ju X, Zhao J, Zhang Y, Xie Y, Polymers, 9, 656 (2017)

[30] Tao YJ, Zhang K, Zhang ZY, Cheng HF, J. Electroanal. Chem., 769, 80 (2016)

[31] Chen S, Zhang D, Wang M, Kong L, Zhao J, New J. Chem., 40, 2178 (2016)

[32] Wang C, Wang M, Zhang Y, Zhao J, Fu C, RSC Adv., 6, 80002 (2016)

[33] Kavak E, Us CN, Yavuz E, Kivrak A, Ozkut MI, Electrochim. Acta, 182, 537 (2015)

[34] Liu Y, Wang M, Zhao J, Cui C, Liu J, RSC Adv., 4, 52712 (2014)