화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.86, 244-250, June, 2020
DOI10.1016/j.jiec.2020.03.018  Export Citation
Effect of cyano substituent on photovoltaic properties of quinoxaline-based polymers
Shinta Lieviana Handoko, Ho Cheol Jin1, Dong Ryeol Whang2, Joo Hyun Kim1, †, and Dong Wook Chang†
  • Department of Industrial Chemistry, Pukyong National University, 48513 Busan, South Korea
  • 1Department of Polymer Engineering, Pukyong National University, 48513 Busan, South Korea
  • 2Department of Materials Science and Engineering, Hannam University, 34430 Daejeon, South Korea
E-mail:,
Three donor-acceptor type quinoxaline-based conjugated polymers, in which electron-donating indacenodithiophene (IDT) and indacenodithieno[3,2-b]thiophene (IDTT) were connected to the electron-accepting 2,3-diphenylquinoxaline (DPQ) derivatives, were synthesized using the Stille coupling reaction. To investigate the effects of the strong electron-withdrawing cyano (-CN) substituent on the photovoltaic properties of polymers, it was selectively introduced in the DPQ unit on the polymer backbone. The combination of IDT and the standard DPQ produced the reference polymer IDT-Qx, while the coupling of IDT and IDTT with mono-CN substituted DPQ provided the target polymers IDT-QxCN and IDTT-QxCN, respectively. Owing to the significant contributions of the CN substituent, IDT-QxCN and IDTT-QxCN exhibited better photovoltaic performances than IDT-Qx reference. Furthermore, the presence of more planar two thieno[3,2-b] thiophenes in IDTT than the two thiophenes in IDT allowed IDTT-QxCN to display the highest power conversion efficiency (5.47%) with an open circuit voltage of 0.95 V, short-circuit current density of 15.30 mA cm-2, and fill factor of 56.95%.
Keywords:Quinoxaline;Indacenodithiophene;Indacenodithieno[3,2-b]thiophene;Cyano substituent
  1. Cheng YJ, Yang SH, Hsu CS, Chem. Rev., 109, 5868 (2009)
  2. Li G, Zhu R, Yang Y, Nat. Photonics, 6, 153 (2012)
  3. Gunes S, Neugebauer H, Sariciftci NS, Chem. Rev., 107(4), 1324 (2007)
  4. Dennler G, Scharber MC, Brabec CJ, Adv. Mater., 21(13), 1323 (2009)
  5. Lu LY, Zheng TY, Wu QH, Schneider AM, Zhao DL, Yu LP, Chem. Rev., 115(23), 12666 (2015)
  6. Hoang MH, Park GE, Phan DL, Ngo TT, Nguyen TV, Park CG, Cho MJ, Choi DH, Macromol. Res., 26(9), 844 (2018)
  7. Lee YJ, Jeon SJ, Choi JY, Moon DK, J. Ind. Eng. Chem., 75, 138 (2019)
  8. Zhu B, Chen X, Huang SI, Peng X, Dyes Pigment., 164, 148 (2019)
  9. Badge SS, Park H, Tran VH, Lee SH, Dyes Pigment., 163, 30 (2019)
  10. Cui Y, Yao H, Zhang J, Zhang T, Wang Y, Hong L, Xian K, Xu B, Zhang S, Peng J, Nat. Commun., 10, 2515 (2019)
  11. Zhu Y, Champion RD, Jenekhe SA, Macromolecules, 39(25), 8712 (2006)
  12. Wu JS, Cheng YJ, Dubosc M, Hsieh CH, Chang CY, Hsu CS, Chem. Commun., 46, 3259 (2010)
  13. Li Y, Accounts Chem. Res., 45, 723 (2012)
  14. Ye L, Zhang S, Zhao W, Yao H, Hou J, Chem. Mater., 26, 3603 (2014)
  15. Huo LJ, He C, Han MF, Zhou EJ, Li YF, J. Polym. Sci. A: Polym. Chem., 45(17), 3861 (2007)
  16. Li J, Grimsdale AC, Chem. Soc. Rev., 39, 2399 (2010)
  17. Hou JH, Chen HY, Zhang SQ, Li G, Yang Y, J. Am. Chem. Soc., 130(48), 16144 (2008)
  18. Qu S, Tian H, Chem. Commun., 48, 3039 (2012)
  19. Zhang Y, Zou J, Yip HL, Chen KS, Zeigler DF, Sun Y, Jen AKY, Chem. Mater., 23, 2289 (2011)
  20. Stuart AC, Tumbleston JR, Zhou HX, Li WT, Liu SB, Ade H, You W, J. Am. Chem. Soc., 135(5), 1806 (2013)
  21. Zhou H, Yang L, Stuart AC, Price SC, Liu S, You W, Angew. Chem.-Int. Edit., 50, 2995 (2011)
  22. Putri SK, Kim YH, Whang DR, Kim JH, Chang DW, Macromol. Rapid Commun., 39, 180026 (2018)
  23. Xu XP, Li Y, Luo MM, Peng Q, Chin. Chem. Lett., 27, 1241 (2016)
  24. Zhang MJ, Guo X, Zhang SQ, Hou JH, Adv. Mater., 26(7), 1118 (2014)
  25. Liao L, Dai LM, Smith A, Durstock M, Lu JP, Ding JF, Tao Y, Macromolecules, 40(26), 9406 (2007)
  26. Putri SK, Kim YH, Whang DR, Lee MS, Kim JH, Chang DW, Org. Electron., 47, 14 (2017)
  27. Xu YX, Chueh CC, Yip HL, Ding FZ, Li YX, Li CZ, Li XS, Chen WC, Jen AKY, Adv. Mater., 24(47), 6356 (2012)
  28. Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Inc.: Wallingford, CT, USA, 1990.
  29. Frisch MJ, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Gaussian Inc. Wallingford CT, pp.34 2009.
  30. Li S, Yan J, Li CZ, Liu F, Shi M, Chen H, Russell TP, J. Mater. Chem. A, 4, 3777 (2016)
  31. Do K, Kim C, Song K, Yun SJ, Lee JK, Ko J, Sol. Energy Mater. Sol. Cells, 115, 52 (2013)
  32. Jia X, Jiang Z, Chen X, Zhou J, Pan L, Zhu F, Sun Z, Huang S, ACS Appl. Mater. Interfaces, 8, 3792 (2016)