Citation: Zhen Wei, Minjie Li, Wencong Lu. Theoretical Study of High-Efficiency Organic Dyes with Different Electron-Withdrawing Groups Based on R6 toward Dye-Sensitized Solar Cells[J]. Acta Physico-Chimica Sinica, ;2021, 37(10): 190508. doi: 10.3866/PKU.WHXB201905084 shu

Theoretical Study of High-Efficiency Organic Dyes with Different Electron-Withdrawing Groups Based on R6 toward Dye-Sensitized Solar Cells

Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China

Corresponding author: Minjie Li, minjieli@shu.edu.cn Wencong Lu, wclu@shu.edu.cn
Received Date: 30 May 2019
Revised Date: 16 July 2019
Accepted Date: 25 July 2019
Available Online: 31 July 2019
Fund Project: the National Key Research and Development Program of China 2016YFB0700504Natural Science Foundation of Shanghai, China 16ZR1411500Science and Technology Commission of Shanghai Municipality, China 18520723500

Dye-sensitized solar cells (DSSCs) are the most promising alternatives to traditional fossil energy because of their advantages of low production cost, facile structure, relatively low environmental impact, relatively high photoelectronic absorption efficiency, and overall high efficiency. In addition, several studies on sensitizers as vital components have been conducted over the last three decades. Compared to metal dyes, metal-free organic dyes have been considered as promising candidates because of their simple fabrication, multiple structures, high molar absorption coefficients, easily tunable properties, and environmental friendliness. In this study, we systematically investigated the optoelectronic properties of six metal-free organic donor-acceptor dyes (RD1–6) derived from the known dye R6 by using the density functional theory (DFT) and time-dependent DFT methods. Cell performance parameters were discussed, including the geometrical and electronic structures, absorption spectrum, adsorption energy, light harvesting efficiency (LHE) curve, predictive short circuit current density (J_sc^Pred.), predictive open circuit voltage (V_oc^Pred.), and theoretical power conversion efficiency (PCE). Results revealed that all the designed dyes exhibited high theoretical PCE. In particular, dyes RD1, 2, and 4–6 showed greater conjugations, and dyes RD1–3 had smaller energy gaps than those of the reference dye. In addition, dyes RD1–3, 5, and 6 exhibited better light harvesting capacities that covered the entire visible region and extended to the near-infrared region with obviously red-shift maximum absorption wavelengths (λ_max), wider LHE curves, and higher J_sc^Pred. as compared to the reference dye. It was critical that dyes RD1 and 2 not only have greater conjugations and narrow band gaps but also good light harvesting capacities with more than 56-nm red-shift maximum absorption wavelengths and broadened LHE curves than those of the reference dye. Notably, mainly because of an average increment of 12.0% of J_sc^Pred., a remarkable increment of the theoretical power conversion efficiency was observed from 12.6% for dye R6 to 14.1% for dyes RD1 and 2. Thus, dyes RD1 and 2 exhibited superior cell performances and could be promising sensitizer candidates for highly efficient DSSCs. These results could be used to guide effective synthetic efforts in the discovery of efficient metal-free organic dye sensitizers in DSSCs.
- Metal-free organic dyes,
- DFT/TD-DFT,
- Light-harvesting ability,
- Optoelectronic property,
- Power conversion efficiency
1. [1]
  O'Regan, B.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0 doi: 10.1038/353737a0
2. [2]
  Yang, L.; Li, Y.; Chen, S.; Zhang, J.; Zhang, M.; Wang, P. Acta Phys. -Chim. Sin. 2016, 32, 329. doi: 10.3866/PKU.WHXB201511031
3. [3]
  Mathew, S.; Yella, A.; Gao, P.; Humphry-Baker, R.; Curchod, B. F.; Ashari-Astani, N. Nat. Chem. 2014, 6, 242. doi: 10.1038/nchem.1861 doi: 10.1038/nchem.1861
4. [4]
  Yang, Z.; Shao, D.; Li, J. Spectrochim. Acta A 2018, 196, 385. doi: 10.1016/j.saa.2018.02.002 doi: 10.1016/j.saa.2018.02.002
5. [5]
  Listorti, A.; O'Regan, B.; Durrant, J. R. Chem. Mater. 2011, 23, 3381. doi: 10.1021/cm200651e doi: 10.1021/cm200651e
6. [6]
  Mohamed, R. E.; Rui, S.; Fadda, A. A.; Etman, H. A.; Eman, H. T.; Ahmed, E. New J. Chem. 2018, 42, 11430. doi: 10.1039/c8nj01482e doi: 10.1039/c8nj01482e
7. [7]
  Jia, H. L.; Peng, Z. J.; Guan, M. Y. New J. Chem. 2018, 42, 13770. doi: 10.1039/c8nj02889c doi: 10.1039/c8nj02889c
8. [8]
  Bisht, R.; Sudhakar, V.; Karjule, N.; Nithyanandhan, J. ACS Appl. Mater. Inter. 2018, 10, 26335. doi: 10.1021/acsami.8b09866 doi: 10.1021/acsami.8b09866
9. [9]
  Santhini, P. V.; Jayadev, V.; Sourava, C.; Sivasankaran, L.; Nitha, P. R.; Chaithanya, M. V.; Rakesh, K. M. New J. Chem. 2019, 43, 862. doi: 10.1039/c8nj04561e doi: 10.1039/c8nj04561e
10. [10]
  Chunxiang D. A.; Kazuhiro, K.; Mizuho, K.; Dai, M.; Kathleen, I.; Moineau, C. C.; Shogo, M. J. Photochem. Photobiol. A 2018, 3659, 403. doi: 10.1016/j.jphotochem.2018.01.021 doi: 10.1016/j.jphotochem.2018.01.021
11. [11]
  Telugu, B. R.; Peddaboodi, G.; Jayraj, V. V.; Saurabh, S. S.; Parameswar, K. I. J. Photochem. Photobiol. A 2019, 6030, 31901. doi: 10.1016/j.jphotochem.2019.02.015 doi: 10.1016/j.jphotochem.2019.02.015
12. [12]
  Xu, Z. J.; Li, Y. Y.; Zhang, W. J. Spectrochim. Acta A 2019, 212, 272. doi: 10.1016/j.saa.2019.01.002 doi: 10.1016/j.saa.2019.01.002
13. [13]
  Yao, Z.; Wu, H.; Li, Y.; Wang, J.; Zhang, J.; Zhang, M.; Guo, Y.; Wang, P. Energy Environ. Sci. 2015, 8, 3192. doi: 10.1039/C5EE02822A doi: 10.1039/C5EE02822A
14. [14]
  Li, Z. G.; Lu, T.; Gao, H.; Zhang, Q.; Li, M. J.; Ren, W.; Lu, W. C. Acta Phys.-Chim. Sin. 2017, 9, 1789. doi: 10.3866/PKU.WHXB201705082
15. [15]
  Yang, Z.; Liu, C.; Li, K.; Cole, J. M.; Cao, D. ACS Appl. Energy Mater. 2018, 1, 1435. doi: 10.1021/acsaem.7b00154 doi: 10.1021/acsaem.7b00154
16. [16]
  Yan, F.; Tian, L.; Xu, Y.; Li, M.; Zhen, W.; Liu, H.; Lu, W. C. Dyes Pigments 2018, 155, 292. doi: 10.1016/j.dyepig.2018.03.045 doi: 10.1016/j.dyepig.2018.03.045
17. [17]
  Wang, L.; Zhang, J.; Duan, Y. C.; Pan, Q. Q.; Wu, Y.; Geng, Y.; Su, Z. M. J. Photochem. Photobiol. A 2019, 369, 150. doi: 10.1039/C8NJ03592J doi: 10.1039/C8NJ03592J
18. [18]
  Li, M.; Kou, L.; Diao, L.; Zhang, Q.; Li, Z.; Wu, Q.; Lu, W.; Pan, D. J. Phys. Chem. A 2015, 119, 3299. doi: 10.1021/acs.jpca.5b00798 doi: 10.1021/acs.jpca.5b00798
19. [19]
  Walid, S.; Zeinab, M. H.; Basant, A. A.; Mohamed, M. E.; Rayhan, M. A.; Nageh, K. A. S. J. Photochem. Photobiol. A 2018, 367, 128. doi: 10.1016/j.jphotochem.2018.08.034 doi: 10.1016/j.jphotochem.2018.08.034
20. [20]
  Puttavva, M.; Goli, N.; Jung, W. Y.; Sun, H. J.; Young, D. G. New J. Chem. 2019, 43, 3017. doi: 10.1039/c8nj06083e doi: 10.1039/c8nj06083e
21. [21]
  Yao, Z.; Zhang, M.; Wu, H.; Yang, L.; Li, R.; Wang, P. J. Am. Chem. Soc. 2015, 137, 3799. doi: 10.1021/jacs.5b01537 doi: 10.1021/jacs.5b01537
22. [22]
  Yao, Z.; Zhang, M.; Li, R.; Yang, L.; Qiao, Y.; Wang, P. Angew. Chem. Int. Ed. 2015, 54, 5994. doi: 10.1002/ange.201501195 doi: 10.1002/ange.201501195
23. [23]
  Yao, Z.; Wu, H.; Li, Y.; Wang, J.; Zhang, J.; Zhang, M.; Guo, Y.; Wang, P. Energ. Environ. Sci. 2015, 8, 3192. doi: 10.1039/c5ee02822a doi: 10.1039/c5ee02822a
24. [24]
  Ren, Y.; Li, Y.; Chen, S.; Liu, J.; Zhang, J.; Wang, P. Energ. Environ. Sci. 2016, 9, 1390. doi: 10.1039/C5EE03309H doi: 10.1039/C5EE03309H
25. [25]
  Ren, Y.; Liu, J.; Zheng, A.; Dong, X.; Wang, P. Adv. Sci. 2017, 4, 1700099. doi: 10.1002/advs.201700099 doi: 10.1002/advs.201700099
26. [26]
  Ren, Y.; Sun, D.; Cao, Y.; Tsao, H. N.; Yuan, Y.; Zakeeruddin, S. M.; Wang, P.; Gratzel, M. J. Am. Chem. Soc. 2018, 140, 2405. doi: 10.1021/jacs.7b12348 doi: 10.1021/jacs.7b12348
27. [27]
  Becke, A. D. J. Chem. Phy. 1993, 98, 5648. doi: 10.1063/1.464913 doi: 10.1063/1.464913
28. [28]
  Chen, S. L.; Yang, L. N.; Li, Z. S. J. Power Sources 2013, 223, 86. doi: 10.1016/j.jpowsour.2012.09.053 doi: 10.1016/j.jpowsour.2012.09.053
29. [29]
  Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669. doi: 10.1002/jcc.10189 doi: 10.1002/jcc.10189
30. [30]
  Wang, Y. L.; Wu, G. S. Acta Phys. -Chim. Sin. 2007, 23, 1831. doi: 10.1016/S1872-1508(07)60086-2
31. [31]
  Hao, D.; Lin, Z.; Xin, Z. Theor. Chem. Acc. 2014, 133, 1. doi: 10.1007/s00214-014-1496-3 doi: 10.1007/s00214-014-1496-3
32. [32]
  Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51. doi: 10.1016/j.cplett.2004.06.011 doi: 10.1016/j.cplett.2004.06.011
33. [33]
  Lu, X.; Shao, Y.; Wei, S.; Zhao, Z.; Li, K.; Guo, C.; Wang, W.; Zhang, M.; Guo, W. J. Mater. Chem. C 2015, 3, 10129. doi: 10.1039/C5TC02286J doi: 10.1039/C5TC02286J
34. [34]
  Heyd, J.; Scuseria, G. E.; Ernzerhof, M. J. Chem. Phys. 2006, 124, 21. doi: 10.1063/1.2204597 doi: 10.1063/1.2204597
35. [35]
  Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811. doi: 10.1021/jp000497z doi: 10.1021/jp000497z
36. [36]
  Becke, A. D. J. Chem. Phys. 1993, 98, 1372. doi: 10.1063/1.464304 doi: 10.1063/1.464304
37. [37]
  Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215. doi: 10.1007/s00214-007-0401-8 doi: 10.1007/s00214-007-0401-8
38. [38]
  Fan, W. J.; Chang, Y. Z.; Zhao, J. L.; Xu, Z. N.; Chen, Y. New J. Chem. 2018, 42, 20163. doi: 10.1016/j.jphotochem.2018.10.022 doi: 10.1016/j.jphotochem.2018.10.022
39. [39]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G., Barone, V.; Petersson, G. A.; Nakatsuji, X.; et al. Gaussian 16, Revision B.03, Gaussian, Inc.: Wallingford, CT, USA, 2016.
40. [40]
  Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580. doi: 10.1002/jcc.22885 doi: 10.1002/jcc.22885
41. [41]
  De Angelis, F.; Tilocca, A.; Selloni, A. J. Am. Chem. Soc. 2004, 126, 15024. doi: 10.1021/ja045152z doi: 10.1021/ja045152z
42. [42]
  De Angelis, F. Chem. Phys. Lett. 2010, 493, 323. doi: 10.1016/j.cplett.2010.05.064 doi: 10.1016/j.cplett.2010.05.064
43. [43]
  Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865. doi: 10.1103/physrevlett.77.3865 doi: 10.1103/physrevlett.77.3865
44. [44]
  Perdew, J. P.; Wang, Y. Phys. Rev. B 2018, 98, 7. doi: 10.1103/PhysRevB.98.079904 doi: 10.1103/PhysRevB.98.079904
45. [45]
  Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833. doi: 10.1063/1.1740588 doi: 10.1063/1.1740588
46. [46]
  Zeng, W.; Liu, T.; Wang, Z.; Tsukimoto, S.; Saito, M.; Ikuhara, Y. Mater. Trans. 2010, 51, 171. doi: 10.2320/matertrans.M2009317 doi: 10.2320/matertrans.M2009317
47. [47]
  Graetzel, M. Acc. Chem. Res. 2009, 42, 1788. doi: 10.1021/ar900141y doi: 10.1021/ar900141y
48. [48]
  Zhang, J.; Li, H. B.; Zhang, J. Z.; Wu, Y.; Geng, Y.; Fu, Q.; Su, Z. M. J. Mater. Chem. A 2013, 1, 14000. doi: 10.1039/c3ta12311a doi: 10.1039/c3ta12311a
49. [49]
  Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Mueller, E.; Liska, P.; Vlachopoulos, N.; Graetzel, M. J. Am. Chem. Soc. 1993, 115, 6382. doi: 10.1021/ja00067a063 doi: 10.1021/ja00067a063
50. [50]
  Marinado, T.; Nonomura, K.; Nissfolk, J.; Karlsson, M. K.; Hagberg, D. P.; Sun, L.; Mori, S.; Hagfeldt, A. Langmuir 2010, 26, 2592. doi: 10.1021/la902897z doi: 10.1021/la902897z
51. [51]
  Feldt, S. M.; Gibson, E. A.; Gabrielsson, E.; Sun, L.; Boschloo, G.; Hagfeldt, A. J. Am. Chem. Soc. 2010, 132, 16714. doi: 10.1021/ja1088869 doi: 10.1021/ja1088869
52. [52]
  Muscat, J. P.; Newns, D. M. Prog. Surf. Sci. 1978, 9, 1. doi: 10.1016/0079-6816(78)90005-9 doi: 10.1016/0079-6816(78)90005-9
53. [53]
  Schiff, L. I. Phys. Today 1949, 24, 70. doi: 10.1119/1.1934159 doi: 10.1119/1.1934159
54. [54]
  Persson, P.; Lundqvist, M. J.; Ernstorfer, R.; Goddard, W. A.; Willig, F. J. Chem. Theory Comput. 2006, 2, 441. doi: 10.1021/ct050141x doi: 10.1021/ct050141x
1. [1]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
2. [2]
  Chaoqun Ma , Yuebo Wang , Ning Han , Rongzhen Zhang , Hui Liu , Xiaofeng Sun , Lingbao Xing . Carbon dot-based artificial light-harvesting systems with sequential energy transfer and white light emission for photocatalysis. Chinese Chemical Letters, 2024, 35(4): 108632-. doi: 10.1016/j.cclet.2023.108632
3. [3]
  Tao Ban , Xi-Yang Yu , Hai-Kuo Tian , Zheng-Qing Huang , Chun-Ran Chang . One-step conversion of methane and formaldehyde to ethanol over SA-FLP dual-active-site catalysts: A DFT study. Chinese Chemical Letters, 2024, 35(4): 108549-. doi: 10.1016/j.cclet.2023.108549
4. [4]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
5. [5]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
6. [6]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
7. [7]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
8. [8]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
9. [9]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
10. [10]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
11. [11]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
12. [12]
  Tao LIU , Yuting TIAN , Ke GAO , Xuwei HAN , Ru'nan MIN , Wenjing ZHAO , Xueyi SUN , Caixia YIN . A photothermal agent with high photothermal conversion efficiency and high stability for tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1622-1632. doi: 10.11862/CJIC.20240107
13. [13]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
14. [14]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
15. [15]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
16. [16]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
17. [17]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
18. [18]
  Yongkang Yue , Zhou Xu , Kaiqing Ma , Fangjun Huo , Xuemei Qin , Kuanshou Zhang , Caixia Yin . HSA shrinkage optimizes the photostability of embedded dyes fundamentally to amplify their efficiency as photothermal materials. Chinese Chemical Letters, 2024, 35(8): 109223-. doi: 10.1016/j.cclet.2023.109223
19. [19]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
20. [20]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(295)
HTML views(15)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142