Abstract
In polymer solar cells (PSCs), twisted polymer donors usually have low photovoltaic efficiencies due to their poor photoactive layer morphologies. Herein, we successfully improved twisted polymer (PBDT-3T) photovoltaic efficiency by employing C=O groups (PBDT-3TCO) to enhance intermolecular interactions. The maximum power conversion efficiency (PCE) of PBDT-3T is only 1.05%, while the PCE of PBDT-3TCO reaches 11.77% in non-fullerene (NF) PSCs. Both polymers-based PSCs show very similar open-circuit voltages but remarkable differences in their short-circuit currents and fill factors. The single crystals of both functionalized terthiophenes with methyl substituents demonstrate that the terthiophene with C=O units changes molecular pattern by forming intra/inter molecular S⋯O and O⋯H interactions but its molecular planarity does not significantly improve. Our comparative studies show that PBDT-3TCO with C=O units possesses a strong aggregation property and optimal photoactive layer morphology in NF PSCs. This study provides important insight into the design of high-performance twisted polymer donors for NF PSCs.
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Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ. Science, 1995, 270: 1789–1791
Huang Y, Kramer EJ, Heeger AJ, Bazan GC. Chem Rev, 2014, 114: 7006–7043
Zhao W, Li S, Yao H, Zhang S, Zhang Y, Yang B, Hou J. J Am Chem Soc, 2017, 139: 7148–7151
Fei Z, Eisner FD, Jiao X, Azzouzi M, Röhr JA, Han Y, Shahid M, Chesman ASR, Easton CD, McNeill CR, Anthopoulos TD, Nelson J, Heeney M. Adv Mater, 2018, 30: 1705209
Zhao J, Li Y, Yang G, Jiang K, Lin H, Ade H, Ma W, Yan H. Nat Energy, 2016, 1: 15027
Yang Y, Zhang ZG, Bin H, Chen S, Gao L, Xue L, Yang C, Li Y. J Am Chem Soc, 2016, 138: 15011–15018
Lin Y, Wang J, Zhang ZG, Bai H, Li Y, Zhu D, Zhan X. Adv Mater, 2015, 27: 1170–1174
Xu X, Yu T, Bi Z, Ma W, Li Y, Peng Q. Adv Mater, 2018, 30: 1703973
Xu SJ, Zhou Z, Liu W, Zhang Z, Liu F, Yan H, Zhu X. Adv Mater, 2017, 29: 1704510
Qian D, Ma W, Li Z, Guo X, Zhang S, Ye L, Ade H, Tan Z’, Hou J. J Am Chem Soc, 2013, 135: 8464–8467
Li Z, Jiang K, Yang G, Lai JYL, Ma T, Zhao J, Ma W, Yan H. Nat Commun, 2016, 7: 13094
Yang B, Zhang S, Chen Y, Cui Y, Liu D, Yao H, Zhang J, Wei Z, Hou J. Macromolecules, 2017, 50: 1453–1462
Mukherjee S, Proctor CM, Bazan GC, Nguyen TQ, Ade H. Adv Energy Mater, 2015, 5: 1500877
Heeger AJ. Adv Mater, 2014, 26: 10–28
Jo J, Na SI, Kim SS, Lee TW, Chung Y, Kang SJ, Vak D, Kim DY. Adv Funct Mater, 2009, 19: 2398–2406
Lim KG, Park JM, Mangold H, Laquai F, Choi TL, Lee TW. ChemSusChem, 2015, 8: 337–344
Hou J, Inganäs O, Friend RH, Gao F. Nat Mater, 2018, 17: 119–128
Liu D, Yang B, Jang B, Xu B, Zhang S, He C, Woo HY, Hou J. Energy Environ Sci, 2017, 10: 546–551
Zhao W, Qian D, Zhang S, Li S, Inganäs O, Gao F, Hou J. Adv Mater, 2016, 28: 4734–4739
Chen S, Liu Y, Zhang L, Chow PCY, Wang Z, Zhang G, Ma W, Yan H. J Am Chem Soc, 2017, 139: 6298–6301
Huang H, Yang L, Facchetti A, Marks TJ. Chem Rev, 2017, 117: 10291–10318
Guo X, Quinn J, Chen Z, Usta H, Zheng Y, Xia Y, Hennek JW, Ortiz RP, Marks TJ, Facchetti A. J Am Chem Soc, 2013, 135: 1986–1996
Dai YZ, Ai N, Lu Y, Zheng YQ, Dou JH, Shi K, Lei T, Wang JY, Pei J. Chem Sci, 2016, 7: 5753–5757
Price SC, Stuart AC, Yang L, Zhou H, You W. J Am Chem Soc, 2011, 133: 4625–4631
Min J, Zhang ZG, Zhang S, Li Y. Chem Mater, 2012, 24: 3247–3254
Chen Z, Cai P, Chen J, Liu X, Zhang L, Lan L, Peng J, Ma Y, Cao Y. Adv Mater, 2014, 26: 2586–2591
Liu Y, Zhao J, Li Z, Mu C, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H. Nat Commun, 2014, 5: 5293
Zhang S, Qin Y, Uddin MA, Jang B, Zhao W, Liu D, Woo HY, Hou J. Macromolecules, 2016, 49: 2993–3000
Liu J, Chen S, Qian D, Gautam B, Yang G, Zhao J, Bergqvist J, Zhang F, Ma W, Ade H, Inganäs O, Gundogdu K, Gao F, Yan H. Nat Energy, 2016, 1: 16089
Chen S, Cho HJ, Lee J, Yang Y, Zhang ZG, Li Y, Yang C. Adv Energy Mater, 2017, 7: 1701125
Wang HJ, Tzeng JY, Chou CW, Huang CY, Lee RH, Jeng RJ. Polym Chem, 2013, 4: 506–519
Xia D, Guo X, Chen L, Baumgarten M, Keerthi A, Müllen K. Angew Chem Int Ed, 2016, 55: 941–944
Wudarczyk J, Papamokos G, Margaritis V, Schollmeyer D, Hinkel F, Baumgarten M, Floudas G, Müllen K. Angew Chem Int Ed, 2016, 55: 3220–3223
Zhang M, Guo X, Ma W, Ade H, Hou J. Adv Mater, 2015, 27: 4655–4660
Takai A, Chen Z, Yu X, Zhou N, Marks TJ, Facchetti A. Chem Mater, 2016, 28: 5772–5783
Blanchard P, Brisset H, Illien B, Riou A, Roncali J. J Org Chem, 1997, 62: 2401–2408
Chaloner PA, Gunatunga SR, Hitchcock PB. J Chem Soc Perkin Trans 2, 1997, 1: 1597–1604
Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K. J Am Chem Soc, 2012, 134: 3498–3507
Zhang S, Yang B, Liu D, Zhang H, Zhao W, Wang Q, He C, Hou J. Macromolecules, 2016, 49: 120–126
Mihailetchi VD, Wildeman J, Blom PWM. Phys Rev Lett, 2005, 94: 126602
Kyaw AKK, Wang DH, Luo C, Cao Y, Nguyen TQ, Bazan GC, Heeger AJ. Adv Energy Mater, 2014, 4: 1301469
Min J, Luponosov YN, Gasparini N, Richter M, Bakirov AV, Shcherbina MA, Chvalun SN, Grodd L, Grigorian S, Ameri T, Ponomarenko SA, Brabec CJ. Adv Energy Mater, 2015, 5: 1500386
Murgatroyd PN. J Phys D-Appl Phys, 1970, 3: 151–156
Azimi H, Senes A, Scharber MC, Hingerl K, Brabec CJ. Adv Energy Mater, 2011, 1: 1162–1168
Cowan SR, Roy A, Heeger AJ. Phys Rev B, 2010, 82: 245207
Riedel I, Parisi J, Dyakonov V, Lutsen L, Vanderzande D, Hummelen J. Adv Funct Mater, 2004, 14: 38–44
Hexemer A, Bras W, Glossinger J, Schaible E, Gann E, Kirian R, MacDowell A, Church M, Rude B, Padmore H. J Phys-Conf Ser, 2010, 247: 012007
Wu Y, Wang Z, Meng X, Ma W. Prog Chem, 2017, 29: 93–101
Gann E, Young AT, Collins BA, Yan H, Nasiatka J, Padmore HA, Ade H, Hexemer A, Wang C. Rev Sci Instrum, 2012, 83: 045110
Carpenter JH, Hunt A, Ade H. J Electron Spectr Related Phenom, 2015, 200: 2–14
Acknowledgements
This work was supported by the National Natural Science Foundation of China (51703228, 21835006, 21504066), the Chinese Academy of Sciences (XDB12030200), and the Ministry of Science and Technology (2016YFA0200700). X-ray data was acquired at beamlines 7.3.3 and 11.0.1.2 at the Advanced Light Source, which is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231. The authors thank Chenhui Zhu at beamline 7.3.3, and Cheng Wang at beamline 11.0.1.2 for assistance with data acquisition.
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An, C., Xin, J., Shi, L. et al. Enhanced intermolecular interactions to improve twisted polymer photovoltaic performance. Sci. China Chem. 62, 370–377 (2019). https://doi.org/10.1007/s11426-018-9408-7
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DOI: https://doi.org/10.1007/s11426-018-9408-7