Synthesis of Quinoxaline-Based Small Molecules Possessing Multiple Electron-Withdrawing Moieties for Photovoltaic Applications

Jun Tae Kim; Ho Cheol Jin; Sella Kurnia Putri; Dong Ryeol Whang; Joo Hyun Kim; Dong Wook Chang

Macromolecular Research, Vol.27, No.12, 1268-1274, December, 2019

DOI10.1007/s13233-020-8002-7 Export Citation

Synthesis of Quinoxaline-Based Small Molecules Possessing Multiple Electron-Withdrawing Moieties for Photovoltaic Applications

Jun Tae Kim, Ho Cheol Jin¹, Sella Kurnia Putri, Dong Ryeol Whang², Joo Hyun Kim^{1, †}, and Dong Wook Chang^†

Department of Industrial Chemistry, Pukyong National University, Busan 48513, Korea
¹Department of Polymer Engineering, Pukyong National University, Busan 48513, Korea
²Linz Institute for Organic Solar Cells (LIOS)/Institute of Physical Chemistry, Johannes Kepler University Linz, 4040, Linz, Austria, Australia

E-mail:,

Three quinoxaline-based small molecules possessing multiple electron-withdrawing moieties were synthesized by the Suzuki coupling reaction for organic photovoltaic cells (OPVs). The electron-donating triarylamine units were linked to both ends of electron-accepting 2,3-diphenyl quinoxaline (DPQ) derivatives with strong electron-withdrawing trifluoromethyl (CF3) moieties to produce a reference D-A-D type small molecule of CF3Qx-0F. Furthermore, one and two fluorine atoms were additionally introduced to the 6,7-positions ofthe DPQ unit of CF3Qx-0F affording CF3Qx-1F and CF3Qx-2F, respectively. Owingto the significant contribution of the electron-withdrawing CF3 and fluorine units, all inverted-type OPVs based on three small molecules exhibited high open circuit voltages greater than 0.82 V. In addition, the power conversion efficiencies (PCEs) of the devices were gradually improved with increasing number of fluorine atoms. The highest PCE (2.82%) with a Voc of 0.88 V, a short-circuit current of 6.38 mA cm?2, and a fill factor of 50.6% was achieved from the device based on CF3Qx-2F.

Keywords:quinoxaline;conjugated small molecules;organic photovoltaic cells;trifluoromethyl;fluorine

[References]

Chen Y, Wan X, Long G, Accounts Chem. Res., 46, 2645 (2013)
Walker B, Kim C, Nguyen TQ, Chem. Mater., 23, 470 (2010)
Bin H, Yao J, Yang Y, Angunawela I, Sun C, Gao L, Ye L, Qiu B, Xue L, Zhu C, Adv. Mater., 30, 170636 (2018)
Lin Y, Li Y, Zhan X, Chem. Soc. Rev., 41, 4245 (2012)
Huo Y, Gong XT, Lau TK, Xiao T, Yan C, Lu X, Lu G, Zhan X, Zhang HL, Chem. Mater., 30, 8661 (2018)
Ilmi R, Haque A, Khan M, Org. Electron., 58, 53 (2018)
E-Ela S, Chen H, Kratzer A, Hirsch A, Brabec CJ, New J. Chem., 40, 2829 (2016)
Baran D, E-Ela S, Kratzer A, Ameri T, Brabec CJ, Hirsch A, RSC Adv., 79, 64724 (2015)
E-Ela S, Vilegas C, Delgado JL, Martin N, New J. Chem., 39, 1477 (2015)
Collins SD, Ran NA, Heiber MC, Nguyen TQ, Adv. Eng. Mater., 7, 160224 (2017)
Wan J, Xu X, Zhang G, Li Y, Feng K, Peng Q, Energ. Environ. Sci., 10, 1739 (2017)
Stuart AC, Tumbleston JR, Zhou HX, Li WT, Liu SB, Ade H, You W, J. Am. Chem. Soc., 135(5), 1806 (2013)
Xu XP, Li Y, Luo MM, Peng Q, Chin. Chem. Lett., 27, 1241 (2016)
Shim JY, Kim T, Kim J, Kim J, Kim I, Kim JY, Suh H, Synth. Met., 205, 112 (2015)
Yuan J, Qiu L, Zhang ZG, Li Y, Chen Y, Zou Y, Nano Energ., 30, 312 (2016)
Casey A, Dimitrov SD, Shakya-Tuladhar P, Fei Z, Nguyen M, Han Y, Anthopoulos TD, Durrant JR, Heeney M, Chem. Mater., 28, 5110 (2016)
Putri SK, Kim YH, Whang DR, Lee MS, Kim JH, Chang DW, Org. Electron., 47, 14 (2017)
Xu S, Feng L, Yuan J, Zhang ZG, Li Y, Peng H, Zou Y, ACS Appl. Mater. Inter., 9, 18816 (2010)
Li M, Zhang G, Xiong L, Zhu M, Pei Y, Peng Q, Liu Y, Dyes Pigment., 158, 402 (2018)
Eastham ND, Dudnik AS, Harutyunyan B, Aldrich TJ, Leonardi MJ, Manley EF, Butler MR, Harschneck T, Ratner MA, Chen LX, ACS Energy Lett., 2, 1690 (2017)
Liao L, Dai LM, Smith A, Durstock M, Lu JP, Ding JF, Tao Y, Macromolecules, 40(26), 9406 (2007)
Kim J, Yun MH, Kim GH, Lee J, Lee SM, Ko SJ, Kim Y, Dutta GK, Moon M, Park SY, ACS Appl. Mater. Inter., 6, 7523 (2014)
Putri SK, Kim YH, Whang DR, Kim JH, Chang DW, Macromol. Rapid Commun., 39, 180026 (2018)
Liang B, Wang L, Xu Y, Shi H, Cao Y, Adv. Funct. Mater., 17(17), 3580 (2007)
Putri SK, Lee MS, Chang DW, Kim JH, Synth. Met., 220, 455 (2016)
Song S, Kim T, Park H, Jin Y, Kim I, Kim JY, Suh H, Synth. Met., 183, 16 (2013)
Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Gaussian 09, revision b. 01, Gaussian, Inc., Wallingford, CT, 6492 (2010).
Yum S, An TK, Wang X, Lee W, Uddin MA, Kim YJ, Nguyen TL, Xu S, Hwang S, Park CE, Chem. Mater., 26, 2147 (2014)
Li Y, Lee TH, Park SY, Uddin MA, Kim T, Hwang S, Kim JY, Woo HY, Polym. Chem., 7, 4638 (2016)
Xue J, Uchida S, Rand BP, Forrest SR, Appl. Phys. Lett., 85, 5757 (2004)

[Referenced By]

[1] Chen Y, Wan X, Long G, Accounts Chem. Res., 46, 2645 (2013)

[2] Walker B, Kim C, Nguyen TQ, Chem. Mater., 23, 470 (2010)

[3] Bin H, Yao J, Yang Y, Angunawela I, Sun C, Gao L, Ye L, Qiu B, Xue L, Zhu C, Adv. Mater., 30, 170636 (2018)

[4] Lin Y, Li Y, Zhan X, Chem. Soc. Rev., 41, 4245 (2012)

[5] Huo Y, Gong XT, Lau TK, Xiao T, Yan C, Lu X, Lu G, Zhan X, Zhang HL, Chem. Mater., 30, 8661 (2018)

[6] Ilmi R, Haque A, Khan M, Org. Electron., 58, 53 (2018)

[7] E-Ela S, Chen H, Kratzer A, Hirsch A, Brabec CJ, New J. Chem., 40, 2829 (2016)

[8] Baran D, E-Ela S, Kratzer A, Ameri T, Brabec CJ, Hirsch A, RSC Adv., 79, 64724 (2015)

[9] E-Ela S, Vilegas C, Delgado JL, Martin N, New J. Chem., 39, 1477 (2015)

[10] Collins SD, Ran NA, Heiber MC, Nguyen TQ, Adv. Eng. Mater., 7, 160224 (2017)

[11] Wan J, Xu X, Zhang G, Li Y, Feng K, Peng Q, Energ. Environ. Sci., 10, 1739 (2017)

[12] Stuart AC, Tumbleston JR, Zhou HX, Li WT, Liu SB, Ade H, You W, J. Am. Chem. Soc., 135(5), 1806 (2013)

[13] Xu XP, Li Y, Luo MM, Peng Q, Chin. Chem. Lett., 27, 1241 (2016)

[14] Shim JY, Kim T, Kim J, Kim J, Kim I, Kim JY, Suh H, Synth. Met., 205, 112 (2015)

[15] Yuan J, Qiu L, Zhang ZG, Li Y, Chen Y, Zou Y, Nano Energ., 30, 312 (2016)

[16] Casey A, Dimitrov SD, Shakya-Tuladhar P, Fei Z, Nguyen M, Han Y, Anthopoulos TD, Durrant JR, Heeney M, Chem. Mater., 28, 5110 (2016)

[17] Putri SK, Kim YH, Whang DR, Lee MS, Kim JH, Chang DW, Org. Electron., 47, 14 (2017)

[18] Xu S, Feng L, Yuan J, Zhang ZG, Li Y, Peng H, Zou Y, ACS Appl. Mater. Inter., 9, 18816 (2010)

[19] Li M, Zhang G, Xiong L, Zhu M, Pei Y, Peng Q, Liu Y, Dyes Pigment., 158, 402 (2018)

[20] Eastham ND, Dudnik AS, Harutyunyan B, Aldrich TJ, Leonardi MJ, Manley EF, Butler MR, Harschneck T, Ratner MA, Chen LX, ACS Energy Lett., 2, 1690 (2017)

[21] Liao L, Dai LM, Smith A, Durstock M, Lu JP, Ding JF, Tao Y, Macromolecules, 40(26), 9406 (2007)

[22] Kim J, Yun MH, Kim GH, Lee J, Lee SM, Ko SJ, Kim Y, Dutta GK, Moon M, Park SY, ACS Appl. Mater. Inter., 6, 7523 (2014)

[23] Putri SK, Kim YH, Whang DR, Kim JH, Chang DW, Macromol. Rapid Commun., 39, 180026 (2018)

[24] Liang B, Wang L, Xu Y, Shi H, Cao Y, Adv. Funct. Mater., 17(17), 3580 (2007)

[25] Putri SK, Lee MS, Chang DW, Kim JH, Synth. Met., 220, 455 (2016)

[26] Song S, Kim T, Park H, Jin Y, Kim I, Kim JY, Suh H, Synth. Met., 183, 16 (2013)

[27] Frisch M, Trucks G, Schlegel H, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G, Gaussian 09, revision b. 01, Gaussian, Inc., Wallingford, CT, 6492 (2010).

[28] Yum S, An TK, Wang X, Lee W, Uddin MA, Kim YJ, Nguyen TL, Xu S, Hwang S, Park CE, Chem. Mater., 26, 2147 (2014)

[29] Li Y, Lee TH, Park SY, Uddin MA, Kim T, Hwang S, Kim JY, Woo HY, Polym. Chem., 7, 4638 (2016)

[30] Xue J, Uchida S, Rand BP, Forrest SR, Appl. Phys. Lett., 85, 5757 (2004)