Synthesis and Opto-Electrical Properties of Novel Conjugated Small Molecule Bearing a B←N Moiety

Ka Yeon Ryu; Dan-Bi Sung; Yong-Ju Kwon; Hyun Yeong Kim; Chongmok Lee; Won-Suk Kim; Kyungkon Kim

Macromolecular Research, Vol.28, No.10, 919-924, September, 2020

DOI10.1007/s13233-020-8113-1 Export Citation

Synthesis and Opto-Electrical Properties of Novel Conjugated Small Molecule Bearing a B←N Moiety

Ka Yeon Ryu, Dan-Bi Sung, Yong-Ju Kwon, Hyun Yeong Kim, Chongmok Lee, Won-Suk Kim^†, and Kyungkon Kim^†

Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Korea

E-mail:,

Effects of the B←N unit on the energy level of conjugated small molecule were investigated by synthesizing a new small molecule BPDPP (3,8-bis(5-(2,5-dioctyl-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)-thiophen-2-yl)-6,6-dioctyl-6H-benzo[3,4] [1,2]azaborolo[1,5-a]pyridin-5-ium-6-uide) via Suzuki coupling. For comparison, CPDPP (6,6′-(5,5′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-dioctyl-3-(thiophen-2-yl)pyrrolo[3,4-c] pyrrole-1,4(2H,5H)-dione)) having the same chemical structure with BPDPP except the B←N unit is synthesized through the same coupling reaction. Absorption spectra and cyclovoltammetry analysis for these small molecules revealed that the B←N unit reduces the band gap of BPDPP by maintaining large oxidation potential. As a result, the blend film of BPDPP and PC71BM maintained 87.4% of the initial absorption intensity after 1sun light soaking test for 315 h. The photo stability of the BPDPP is significantly higher than the blend film of P3HT: PC71BM, which maintained only 19.8% of the initial absorption intensity only after light soaking for 23 h.

Keywords:organic solar cell;B-N containing dye;small molecule organic solar cell;stability

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[2] Qian X, Lan X, Yan R, He Y, Huang J, Hou L, Electrochim. Acta, 232, 337 (2017)

[3] Qian X, Wang X, Shao L, Li H, Yan R, Hou L, J. Power Sources, 326, 129 (2017)

[4] Wakamiya A, Taniguchi T, Yamaguchi S, Angew. Chem.-Int. Edit., 45, 3170 (2006)

[5] Zhao R, Dou D, Xie Z, Liu J, Wang L, Angew. Chem.-Int. Edit., 55, 5313 (2016)

[6] Long XJ, Dou CD, Liu J, Wang LX, Macromolecules, 50(21), 8521 (2017)

[7] Guo YQ, Wang Y, Song LC, Liu F, Wan X, Zhang H, Chen Y, Chem. Mater., 29, 3694 (2017)

[8] Wang JL, Liu KK, Liu S, Xiao F, Chang ZF, Zheng YQ, Dou JH, Zhang RB, Wu HB, Pei J, Chem. Mater., 29, 1036 (2017)

[9] Tamayo AB, Walker B, Nguyen TQ, J. Phys. Chem. C, 112, 11545 (2008)

[10] Dou C, Ding Z, Zhang Z, Xie Z, Liu J, Wang L, Angew. Chem.-Int. Edit., 54, 3648 (2015)

[11] Min Y, Dou C, Tian H, Geng Y, Liu J, Wang L, Angew. Chem.-Int. Edit., 57, 2000 (2018)

[12] Sun YM, Seo JH, Takacs CJ, Seifter J, Heeger AJ, Adv. Mater., 23(14), 1679 (2011)

[13] Marrocchi A, Facchetti A, Lanari D, Petrucci C, Vaccaro L, Energy Environ. Sci., 9, 763 (2016)

[14] Zhang L, Zeng S, Yin L, Ji C, Li K, Li Y, Wang Y, New J. Chem., 37, 632 (2013)

[15] Ishida N, Moriya T, Goya T, Murakami M, J. Org. Chem., 75, 8709 (2010)

[16] Chen H, Hu D, Yang Q, Gao J, Fu J, Yang K, He H, Chen S, Kan Z, Duan T, Joule, 3, 3034 (2019)

[17] Bathula C, Mallikarjuna K, Kadam A, Shrestha NK, Khadtare S, Mane SD, Kim H, Inorg. Chem. Commun., 102, 20 (2019)

[18] Lee CJ, Jradi FM, Mitchell VD, White J, McNeill CR, Subbiah J, Marder S, Jones DJ, J. Mater. Chem. C, 8, 567 (2020)

[19] Huang J, Zhan C, Zhang X, Zhao Y, Lu Z, Jia H, Jiang B, Ye J, Zhang S, Tang A, ACS Appl. Mater. Interfaces, 5, 2033 (2013)

[20] Peng Q, Huang Q, Hou X, Chang P, Xu J, Deng S, Chem. Commun., 48, 11452 (2012)

[21] Scharber MC, Wuhlbacher D, Koppe M, Denk P, Waldauf C, Heeger AJ, Brabec CL, Adv. Mater., 18(6), 789 (2006)

[22] Perez LA, Chou KW, Love JA, van der Poll TS, Smilgies DM, Nguyen TQ, Kramer EJ, Amassian A, Bazan GC, Adv. Mater., 25(44), 6380 (2013)

[23] Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ, Science, 270(5243), 1789 (1995)

[24] Yang YM, Chen W, Dou L, Chang WH, Duan HS, Bob B, Li G, Yang Y, Nat. Photonics, 9, 190 (2015)

[25] Irwin MD, Buchholz DB, Hains AW, Chang RP, Marks TJ, Proc. Natl. Acad. Sci., 105, 2783 (2008)