Citation: Tang Yunyu, Liu Xiujun, Wang Yueqiang, Liu Qingyun, Li Xin, Li Chengjie, Shen Xiaosheng, Xie Yongshu. Solar cells sensitized by porphyrin dyes containing a substituted carbazole donor with synergistically extended absorption and suppressed the dye aggregation[J]. Chinese Chemical Letters, ;2020, 31(7): 1927-1930. doi: 10.1016/j.cclet.2019.12.038 shu

Solar cells sensitized by porphyrin dyes containing a substituted carbazole donor with synergistically extended absorption and suppressed the dye aggregation

Tang Yunyu ^a ,
Liu Xiujun ^b ,
Wang Yueqiang ^b ,
Liu Qingyun ^c,*, ,
Li Xin ^d ,
Li Chengjie ^b ,
Shen Xiaosheng ^a,*, ,
Xie Yongshu ^b,*,

a.
Laboratory of Quality Safety and Processing for Aquatic Product, East China Sea Fisheries Research Institute, Chinese Academy of Fishery Sciences, Shanghai 200090, China
b.
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
c.
College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590, China
d.
Division of Theoretical Chemistry and Biology, School of Biotechnology, KTH Royal Institute of Technology, Stockholm SE-10691, Sweden

qyliu@sdust.edu.cn

foodsmc98@126.com

yshxie@ecust.edu.cn

Received Date: 25 October 2019
Revised Date: 23 December 2019
Accepted Date: 30 December 2019
Available Online: 31 December 2019

Figures(3)

To achieve high power conversion efficiency (PCE), three porphyrin sensitizers have been synthesized and explored to simultaneously enhance the photocurrent (J_sc) and photovoltage (V_oc). On basis of the XW4, a benzothiadiazole (BTD) unit has been introduced to afford XW57 with the aim to extend the absorption wavelength and enhance the light harvesting ability. As a result, a J_sc of 13.72 mA/cm² has been obtained for XW57, higher than that of XW4. On this basis, XW58 has been prepared by modifying the carbazole-based donor with two bulky dihexyloxyphenyl groups, and the superior anti-aggregation character raises the V_oc from 781 mV (XW4) to 844 mV. When both the BTD unit and the bulky groups are introduced to the acceptor and donor units, respectively, the resulting sensitizer XW59 exhibits a highest PCE value of 7.34% with synergistically enhanced J_sc of 13.19 mA/cm² and V_oc of 793 mV. These results provide further insight into developing high performance dye-sensitized solar cells
- Dye-sensitized solar cells,
- Porphyrin,
- Sensitizers,
- Carbazole,
- Bulky groups
1. [1]
  B. O'Regan, M. Grätzel, Nature 353(1991) 737-740. doi: 10.1038/353737a0
2. [2]
  H. Tian, S.C. Huang, S.C. Zhou, Acta Phys. Chim. Sin. 4(1988) 314-319. doi: 10.3866/PKU.WHXB19880317
3. [3]
  A. Yella, H.W. Lee, H.N. Tsao, et al., Science 334(2011) 629-634. doi: 10.1126/science.1209688
4. [4]
  M.K. Nazeeruddin, A. Kay, I. Rodicio, et al., J. Am. Chem. Soc. 115(1993) 6382-6390. doi: 10.1021/ja00067a063
5. [5]
  Y.J. Xie, Z. Li, Mater. Chem. Front. 4(2020) 317-331. doi: 10.1039/C9QM00580C
6. [6]
  T. Hua, Z.S. Huang, K. Cai, et al., Electrochim. Acta 302(2019) 225-233. doi: 10.1016/j.electacta.2019.02.013
7. [7]
  B. Pan, Y.Z. Zhu, D. Ye, et al., New J. Chem. 42(2018) 4133-4141. doi: 10.1039/C7NJ04629D
8. [8]
  Y. Wang, B. Chen, W. Wu, et al., Angew. Chem. Int. Ed. 53(2014) 10779-10783. doi: 10.1002/anie.201406190
9. [9]
  Y. Xie, Y. Tang, W. Wu, et al., J. Am. Chem. Soc. 137(2015) 14055-14058. doi: 10.1021/jacs.5b09665
10. [10]
  Y. Tang, Y. Wang, X. Li, et al., ACS Appl. Mater. Interfaces 7(2015) 27976-27985. doi: 10.1021/acsami.5b10624
11. [11]
  K. Zeng, Y. Lu, W. Tang, et al., Chem. Sci. 10(2019) 2186-2192. doi: 10.1039/C8SC04969F
12. [12]
  Y. Lu, H. Song, X. Li, et al., ACS Appl. Mater. Interfaces 11(2019) 5046-5054. doi: 10.1021/acsami.8b19077
13. [13]
  Y. Xie, W. Wu, H. Zhu, et al., Chem. Sci. 7(2016) 544-549. doi: 10.1039/C5SC02778K
14. [14]
  Y. Lu, Y. Cheng, C. Li, et al., Sci. China Chem. 62(2019) 994-1000. doi: 10.1007/s11426-019-9471-y
15. [15]
  H. Song, Q. Liu, Y. Xie, Chem. Commun. 54(2018) 1811-1824. doi: 10.1039/C7CC09671B
16. [16]
  M. Urbani, M. Grätzel, M.K. Nazeeruddin, Chem. Rev. 114(2014) 12330-12396. doi: 10.1021/cr5001964
17. [17]
  Y.Q. Wang, L. Xu, X.D. Wei, et al., New J. Chem. 38(2014) 3227-3235. doi: 10.1039/C4NJ00651H
18. [18]
  Y. Lu, Q. Liu, J. Luo, et al., ChemSusChem 12(2019) 2802-2809. doi: 10.1002/cssc.201900139
19. [19]
  K.W. Zeng, W.Q. Tang, C.J. Li, et al., J. Mater. Chem. A 7(2019) 20854-20860. doi: 10.1039/C9TA06911A
20. [20]
  C.J. Li, J.L. Zhang, J.X. Song, et al., Sci. China Chem. 61(2018) 511-514. doi: 10.1007/s11426-018-9245-6
21. [21]
  H.L. Song, J. Zhang, J.M. Jin, J. Mater. Chem. C 6(2018) 3927-3936. doi: 10.1039/C8TC00610E
22. [22]
  A. Yella, C.L. Mai, S.M. Zakeeruddin, et al., Angew. Chem. Int. Ed. 53(2014) 2973-2977. doi: 10.1002/anie.201309343
23. [23]
  Y.C. Chang, C.L. Wang, T.Y. Pan, Chem. Commun. 47(2011) 8910-8912. doi: 10.1039/c1cc12764k
24. [24]
  M.K. Nazeeruddin, F. De Angelis, S. Fantacci, et al., J. Am. Chem. Soc. 127(2005) 16835-16847. doi: 10.1021/ja052467l
25. [25]
  C.H. Wu, M.C. Chen, P.C. Su, et al., J. Mater. Chem. A 2(2014) 991-999. doi: 10.1039/C3TA14208F
26. [26]
  V. Piradi, X. Xu, Z. Wang, et al., ACS Appl. Mater. Interfaces 11(2019) 6283-6291. doi: 10.1021/acsami.8b19240
27. [27]
  Z. Yao, H. Wu, Y. Ren, et al., Energy Environ. Sci. 8(2015) 1438-1442. doi: 10.1039/C4EE03934C
28. [28]
  P. Gautam, R. Misra, S.A. Siddiqui, et al., ACS Appl. Mater. Interfaces 719(2015) 10283-10292.
29. [29]
  H. Zhu, W. Li, Y. Wu, et al., ACS Sustain. Chem. Eng. 2(2014) 1026-1034. doi: 10.1021/sc500035j
30. [30]
  J.P. Hill, Angew. Chem. Int. Ed. 55(2016) 2976-2978. doi: 10.1002/anie.201511506
31. [31]
  H.P. Wu, Z.W. Ou, T.Y. Pan, et al., Energy Environ. Sci. 5(2012) 9843-9848. doi: 10.1039/c2ee22870j
32. [32]
  M. Zhang, Y. Wang, M. Xu, et al., Energy Environ. Sci. 6(2013) 2944-2949. doi: 10.1039/c3ee42331j
33. [33]
  H.L. Jia, M.D. Zhang, W. Yan, et al., J. Mater. Chem. A 4(2016) 11782-11788. doi: 10.1039/C6TA03740B
34. [34]
  W.I. Hung, Y.Y. Liao, T.H. Lee, et al., Chem. Commun. 51(2015) 2152-2155. doi: 10.1039/C4CC09294E
35. [35]
  X. Zhang, J. Mao, D. Wang, et al., ACS Appl. Mater. Interfaces 7(2015) 2760-2771. doi: 10.1021/am507824h
36. [36]
  Z. Wang, M. Liang, Y. Tan, et al., J. Mater. Chem. A 3(2015) 4865-4874. doi: 10.1039/C4TA06705C
37. [37]
  X. Li, Z. Zheng, W. Jiang, et al., Chem. Commun. 51(2015) 3590-3592. doi: 10.1039/C4CC08539F
38. [38]
  S.A. Sapp, C.M. Elliott, C. Contado, et al., J. Am. Chem. Soc. 124(2002) 11215-11222. doi: 10.1021/ja027355y
39. [39]
  Y. Hao, Y. Saygili, J. Cong, et al., ACS Appl. Mater. Interfaces 8(2016) 32797-32804. doi: 10.1021/acsami.6b09671
40. [40]
  H.N. Tsao, T. Moehl, J.H. Yum, et al., ChemSusChem 4(2011) 591-594. doi: 10.1002/cssc.201100120
41. [41]
  S.M. Feldt, E.A. Gibson, E. Gabrielsson, et al., J. Am. Chem. Soc. 132(2010) 16714-16724. doi: 10.1021/ja1088869
42. [42]
  L. Zhang, J.M. Cole, J. Mater. Chem. A 5(2017) 19541-19559. doi: 10.1039/C7TA05632J
43. [43]
  H.H. Chou, K.S.K. Reddy, H.P. Wu, et al., ACS Appl. Mater. Interfaces 8(2016) 3418-3427. doi: 10.1021/acsami.5b11554
44. [44]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09 Revision A.2, Gaussian Inc., Wallingford CT, 2009.
45. [45]
  A.D. Becke, J. Chem. Phys. 98(1993) 5648-5652. doi: 10.1063/1.464913
46. [46]
  C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37(1988) 785-789. doi: 10.1103/PhysRevB.37.785
47. [47]
  W.J. Hehre, R. Ditchfield, J.A. Pople, J. Chem. Phys. 56(1972) 2257-2261. doi: 10.1063/1.1677527
48. [48]
  P. Dai, H. Dong, M. Liang, et al., ACS Sustain. Chem. Eng. 5(2017) 97-104. doi: 10.1021/acssuschemeng.6b00706
49. [49]
  Y.K. Eom, S.H. Kang, I.T. Choi, et al., J. Mater. Chem. A 5(2017) 2297-2308. doi: 10.1039/C6TA09836C
50. [50]
  Y. Ren, D. Sun, Y. Cao, et al., J. Am. Chem. Soc. 140(2018) 2405-2408. doi: 10.1021/jacs.7b12348
51. [51]
  T. Wei, X. Sun, X. Li, et al., ACS Appl. Mater. Interfaces 7(2015) 21956-21965. doi: 10.1021/acsami.5b06610
52. [52]
  G. Yang, Y. Tang, X. Li, et al., ACS Appl. Mater. Interfaces 9(2017) 36875-36885. doi: 10.1021/acsami.7b12066
1. [1]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
2. [2]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
3. [3]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
4. [4]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
5. [5]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
6. [6]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
7. [7]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
8. [8]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
9. [9]
  Cheng-Shuang Wang , Bing-Yu Zhou , Yi-Feng Wang , Cheng Yuan , Bo-Han Kou , Wei-Wei Zhao , Jing-Juan Xu . Bifunctional iron-porphyrin metal-organic frameworks for organic photoelectrochemical transistor gating and biosensing. Chinese Chemical Letters, 2025, 36(3): 110080-. doi: 10.1016/j.cclet.2024.110080
10. [10]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
11. [11]
  Chengcheng Xie , Chengyi Xiao , Hongshuo Niu , Guitao Feng , Weiwei Li . Mesoporous organic solar cells. Chinese Chemical Letters, 2024, 35(11): 109849-. doi: 10.1016/j.cclet.2024.109849
12. [12]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
13. [13]
  Xingyan Liu , Chaogang Jia , Guangmei Jiang , Chenghua Zhang , Mingzuo Chen , Xiaofei Zhao , Xiaocheng Zhang , Min Fu , Siqi Li , Jie Wu , Yiming Jia , Youzhou He . Single-atom Pd anchored in the porphyrin-center of ultrathin 2D-MOFs as the active center to enhance photocatalytic hydrogen-evolution and NO-removal. Chinese Chemical Letters, 2024, 35(9): 109455-. doi: 10.1016/j.cclet.2023.109455
14. [14]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
15. [15]
  Chi Li , Peng Gao . Is dipole the only thing that matters for inverted perovskite solar cells?. Chinese Journal of Structural Chemistry, 2024, 43(6): 100324-100324. doi: 10.1016/j.cjsc.2024.100324
16. [16]
  Hang Chen , Chengzhi Cui , Hebo Ye , Hanxun Zou , Lei You . Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups. Chinese Chemical Letters, 2024, 35(5): 109145-. doi: 10.1016/j.cclet.2023.109145
17. [17]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
18. [18]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
19. [19]
  Kangrong Yan , Ziqiu Shen , Yanchun Huang , Benfang Niu , Hongzheng Chen , Chang-Zhi Li . Curing the vulnerable heterointerface via organic-inorganic hybrid hole transporting bilayers for efficient inverted perovskite solar cells. Chinese Chemical Letters, 2024, 35(6): 109516-. doi: 10.1016/j.cclet.2024.109516
20. [20]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(820)
HTML views(81)

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