Citation: Zhou Xinyun, Xie Lingchao, Wu Kaile, Tan Songting. Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2589-2598. doi: 10.6023/cjoc201902023 shu

Synthesis and Photovoltaic Properties of Organic Dyes Containing Dendritic and 3D Triphenylamine Derivatives

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105

Corresponding author: Tan Songting, tanst2008@163.com

^†

Received Date: 21 February 2019
Revised Date: 14 April 2019
Available Online: 19 September 2019
Fund Project: the National Natural Science Foundation of China 21875204Project supported by the National Natural Science Foundation of China (Nos. 21875204, 51173154)the National Natural Science Foundation of China 51173154

Figures(10)

Three organic dyes with dendritic and 3D triphenylamine derivatives as the donor unit, benzoic acid as the acceptor unit and benzothiadiazole (BT) or difluorobenzothiadiazole (DFBT) as the second acceptor were designed and synthesized. The influences of different donors and second acceptors on the photophysical, electrochemical and photovoltaic properties of dye-sensitizers were systematically investigated. The organic dye with dendritic triphenylamine derivative as a donor unit possesses a higher molar absorption coefficient, and the organic dye with 3D triphenylamine derivative (IDTTPA) as a donor unit has a broader absorption spectrum. The dye-sensitized solar cells based on three organic dyes achieved power conversion efficiencies of 5.27%, 4.22% and 5.50%, respectively. After optimizing the battery with 1 mmol·L^-1 co-adsorbent chenodeoxycholic acid (CDCA), the power conversion efficiencies of the organic dyes were increased to 5.46%, 4.98% and 6.26%, respectively.
- triphenylamine,
- benzothiadiazole,
- organic dye,
- photovoltaic property
1. [1]
  O'regan, B.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0
2. [2]
  Hagfeldt, A.; Boschloo, G.; Sun, L. C.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595. doi: 10.1021/cr900356p
3. [3]
  Clifford, J. N.; Martínez-Ferrero, E.; Viterisi, A.; Palomares, E. Chem. Soc. Rev. 2011, 40, 1635. doi: 10.1039/B920664G
4. [4]
  Wu, Y.-Z.; Zhu, W. H. Chem. Soc. Rev. 2013, 42, 2039. doi: 10.1039/C2CS35346F
5. [5]
  Kou, D.-X.; Liu, W.-Q.; Hu, L.-H.; Chen, S.-H.; Huang, Y.; Dai, S.-Y. Acta Chim. Sinica 2013, 71, 1149 (in Chinese).
6. [6]
  Feng, X.-M.; Huang, X.-W.; Tan, Z.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2011, 69, 653 (in Chinese).
7. [7]
  Huang, X.-W.; Deng, J.-Y.; Xu, L.; Shen, P.; Zhao, B.; Tan, S.-T. Acta Chim. Sinica 2012, 70, 1604 (in Chinese).
8. [8]
  Li, J.; Kong, F.-T.; Zhang, C.-N.; Liu, W.-Q.; Dai, S.-Y. Acta Chim. Sinica 2010, 68, 1357 (in Chinese).
9. [9]
  Tang, X.; Wang, Y.-X. Acta Chim. Sinica 2013, 71, 193 (in Chinese).
10. [10]
  Wang, J.-W.; Li, Y.; Xu, Y.-L.; Li, Y.; Shen, K.-H. Acta Chim. Sinica 2012, 70, 1278 (in Chinese). doi: 10.3969/j.issn.0251-0790.2012.06.026
11. [11]
  He, J.-J.; Chen, S.-X.; Wang, T.-T.; Zeng, H.-P. Chin. J. Org. Chem. 2012, 32, 472 (in Chinese).
12. [12]
  Cao, Y.-M.; Bai, Y.; Yu, Q.-J.; Cheng, Y.-M.; Liu, S.; Shi, D.; Gao, F.-F.; Wang, P. J. Phys. Chem. C 2009, 113, 6290.
13. [13]
  Yella, A.; Mai, C. L.; Zakeeruddin, S. M.; Chang, S. N.; Hsieh, C. H.; Yeh, C. Y.; Grätzel, M. Angew. Chem., Int. Ed. 2014, 53, 2973. doi: 10.1002/anie.201309343
14. [14]
  Gupta, K.; Singh, S. P.; Islam, A.; Han, L.; Chandrasekharam, M. Electrochim. Acta 2015, 174, 581. doi: 10.1016/j.electacta.2015.05.158
15. [15]
  Mishra, A.; Fischer, M. K.; Bäuerle, P. Angew. Chem., Int. Ed. 2009, 48, 2474. doi: 10.1002/anie.200804709
16. [16]
  Han, L.; Zhou, X.; Ye, Q.; Li, Y.-J.; Gao, J.-R. Chin. J. Org. Chem. 2013, 33, 1000 (in Chinese).
17. [17]
  Wang, Z.-S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. J. Phys. Chem. C 2008, 112, 17011. doi: 10.1021/jp806927b
18. [18]
  Su, J.-Y.; Chen, Y.; Wu, Y.-G.; Ghimire, R. P.; Xu, Y.-J.; Liu, X.-J.; Wang, Z.-H.; Liang, M. Electrochim. Acta 2017, 254, 191. doi: 10.1016/j.electacta.2017.09.133
19. [19]
  Han, L.; Wu, L.; Tong, Y.-Z.; Zu, X.-Y.; Jiang, S.-L. Chin. J. Org. Chem. 2017, 37, 2940 (in Chinese).
20. [20]
  Chen, S.-G.; Jia, H.-L.; Ju, X.-H.; Zheng, H.-G. Dyes Pigm. 2017, 146, 127. doi: 10.1016/j.dyepig.2017.06.068
21. [21]
  Zhu, B.-Y.; Wu, L.; Ye, Q.; Gao, J.-R.; Han, L. Tetrahedron 2017, 73, 6307. doi: 10.1016/j.tet.2017.09.018
22. [22]
  Liang, M.; Xu, Y.-J.; Wang, X.-D.; Liu, X.-J.; Sun, Z.; Xue, S. Acta Chim. Sinica 2011, 69, 2092 (in Chinese).
23. [23]
  Cao, Z.-C.; He, Z.; Deng, L.-J.; Tan, S.-T. Chin. J. Org. Chem. 2014, 34, 340 (in Chinese).
24. [24]
  Li, Q.-Q.; Shi, J.; Li, H.-Y.; Li, S.; Zhong, C.; Guo, F.-L.; Peng, M.; Hua, J.-L.; Qin, J.-G.; Li, Z. J. Mater. Chem. 2012, 22, 6689. doi: 10.1039/c2jm30200d
25. [25]
  Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun. 2008, 5194.
26. [26]
  Wu, Y.-Z.; Zhang, X.; Li, W.-Q.; Wang, Z.-S.; Tian, H.; Zhu, W.-H. Adv. Energy Mater. 2012, 2, 149. doi: 10.1002/aenm.201100341
27. [27]
  Li, Q.-Q.; Lu, L.-L.; Zhong, C.; Shi, J.; Huang, Q.; Jin, X.-B.; Peng, T.-Y.; Qin, J.-G.; Li, Z. J. Phys. Chem. B 2009, 113, 14588. doi: 10.1021/jp906334w
28. [28]
  Kakiage, K.; Aoyama, Y.; Yano, T.; Oya, K.; Fujisawa, J.; Hanaya, M. Chem. Commun. 2015, 51, 15894. doi: 10.1039/C5CC06759F
29. [29]
  Liu, Z.-X.; Duan, K.-K.; Guo, H.; Deng, Y.-H.; Huang, H.-L.; Yi, X.-Y.; Chen, H.-J.; Tan, S.-T. Dyes Pigm. 2017, 140, 312. doi: 10.1016/j.dyepig.2017.01.026
30. [30]
  Zhu, H.-B.; Li, W.-Q.; Wu, Y.-Z.; Liu, B.; Zhu, S.-Q.; Li, X.; Agren, H.; Zhu, W.-H. ACS Sustainable Chem. Eng. 2014, 2, 1026. doi: 10.1021/sc500035j
31. [31]
  Han, L.; Zu, X.-Y.; Cui, Y.-H.; Wu, H.-B.; Ye, Q.; Gao, J.-R. Org. Electron. 2014, 15, 1536. doi: 10.1016/j.orgel.2014.04.016
32. [32]
  Pan, B.; Zhu, Y.-Z.; Qiu, C.-J.; Wang, B.; Zheng, J.-O. Acta Chim. Sinica 2018, 76, 215 (in Chinese).
33. [33]
  Chen, H.-J.; Huang, H.; Huang, X.-W.; Clifford, J. N.; Forneli, A.; Palomares, E.; Zheng, X.-Y.; Zheng, L.-P.; Wang, X.-Y.; Shen, P.; Zhao, B.; Tan, S.-T. J. Phys. Chem. C 2010, 114, 3280.
34. [34]
  Huang, H.-L.; Chen, H.-J.; Long, J.; Wang, G.; Tan, S.-T. J. Power Sources 2016, 326, 438. doi: 10.1016/j.jpowsour.2016.06.099
35. [35]
  Forster, F.; Rendón López, V.-M.; Oestreich, M. J. Am. Chem. Soc. 2018, 140, 1259. doi: 10.1021/jacs.7b13088
36. [36]
  Song, X.-R.; Zhang, W.-W.; Li, X.; Jiang, H.-Y.; Shen, C.; Zhu, W.-H. J. Mater. Chem. C 2016, 4, 9203. doi: 10.1039/C6TC03418G
37. [37]
  Liu, Y.-H.; Cao, Y.-M.; Zhang, W.-W.; Stojanovic, M.; Dar, M I.; Péchy, P.; Saygili, Y.; Hagfeldt, A.; Zakeeruddin, S. M.; Grätzel, M. Angew. Chem., Int. Ed. 2018, 130, 14321. doi: 10.1002/ange.201808609
38. [38]
  Chen, R.-K.; Yang, X.-C.; Tian, H.-N.; Sun, L.-C. J. Photochem. Photobiol. A 2007, 189, 295. doi: 10.1016/j.jphotochem.2007.02.018
39. [39]
  Shen, P.; Liu, Y.-J.; Huang, X.-W.; Zhao, B.; Xiang, N.; Fei, J.-J.; Liu, L.-M.; Wang, X.-Y.; Huang, H.; Tan, S.-T. Dyes Pigm. 2009, 83, 187. doi: 10.1016/j.dyepig.2009.04.005
40. [40]
  Liu, X.-S.; Cao, Z.-C.; Huang, H.-L.; Liu, X.-X.; Tan, Y.-Z.; Chen, H.-J.; Pei, Y.; Tan, S.-T. J. Power Sources 2014, 248, 400. doi: 10.1016/j.jpowsour.2013.09.106
41. [41]
  Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Ohga, Y.; Shinpo, A.; Suga, S.; Sayama, K.; Sugihara, H.; Arakawa, H. J. Phys. Chem. B 2003, 107, 597. doi: 10.1021/jp026963x
1. [1]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
4. [4]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
5. [5]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
6. [6]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
7. [7]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
8. [8]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
9. [9]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
10. [10]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
11. [11]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
12. [12]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
13. [13]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
14. [14]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
15. [15]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
16. [16]
  Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
17. [17]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
18. [18]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125
19. [19]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
20. [20]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1131)
HTML views(150)

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