Citation: ZHAN Wei-Shen, LI Rui, PAN Shi, GUO Ying-Nan, ZHANG Yi. Extension of Conjugate π Bridge in Dye Molecules for Dye-Sensitized Solar Cells[J]. Acta Physico-Chimica Sinica, ;2013, 29(02): 255-262. doi: 10.3866/PKU.WHXB201211221 shu

Extension of Conjugate π Bridge in Dye Molecules for Dye-Sensitized Solar Cells

1.
Institute of Near-Field Optics and Nanotechnology, School of Physics and Optoelectronic Technology, Dalian University of Technology, Dalian 116024, Liaoning Province, P. R. China

Received Date: 7 August 2012
Available Online: 22 November 2012
Fund Project: 国家自然科学基金(10974025, 61137005)资助项目 (10974025, 61137005)

Taking dye D5 molecules as the prototype, different types and different elemental quantities of conjugate π bridge was used to design D-π-A organic molecules. Density functional theory (DFT) and timedependent density functional theory (TDDFT) were adopted to simulate the geometric structures, molecular orbital energy levels, and UV-Vis absorption spectra of the molecules, with the aim of finding conjugate π bridge in the sensitizer molecules for dye-sensitized solar cells (DSSCs). The absorption spectra of the molecules using “methenyl chains”,“furan rings” or “thiophene rings”,“methenyl chains and furan rings”, or “methenyl chains and thiophene rings” as conjugate π bridge showed a gradually increasing red-shifting trend. With increases in the number of conjugate π bridge elements, the absorption spectrum showed an intense red-shift, which weakened gradually; under the same conditions, the lowest unoccupied molecular orbital (LUMO) energy level of the molecules gradually decreased, and the highest occupied molecular orbital (HOMO) energy level gradually increased. The HOMO energy levels of the molecules with three“methenyl chain and furan ring”or“methenyl chain and thiophene ring”elements as conjugate π bridge were higher than the energy level of the redox electrolyte; in polar solutions, the HOMO energy levels of the molecules adopting two “methenyl chain and furan ring” or “methenyl chain and thiophene ring” elements as conjugate π bridge were higher than the energy level of the redox electrolyte. The absorption spectra of the organic sensitizer molecules with several “methenyl chain and furan ring” or “methenyl chain and thiophene ring” elements as conjugate π bridge showed an intense red-shift. These results showed that for DSSCs sensitizer molecules, it is not necessary to have many conjugate π bridge elements; one to two elements is typically enough.
- Dye-sensitized solar cell,
- Organic photosensitizer,
- Conjugated bridge,
- Density functional theory,
- Methenyl chain,
- Furan ring,
- Thiophene ring
1. [1]
  
  (1) O'Regan, B.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0
2. [2]
  (2) Grätzel, M. J. Photochem. Photobiol. C 2003, 4, 145. doi: 10.1016/S1389-5567(03)00026-1
3. [3]
  (3) Grätzel, M. J. Photochem. Photobiol. A 2004, 164, 3. doi: 10.1016/j.jphotochem.2004.02.023
4. [4]
  (4) Nazeeruddin, M. K.; Klein, C.; Liska, P.; Grätzel, M. Coord.Chem. Rev. 2005, 249, 1460. doi: 10.1016/j.ccr.2005.03.025
5. [5]
  (5) Grätzel, M. Inorg. Chem. 2005, 44, 6841.
6. [6]
  (6) Peter, L. M. Phys. Chem. Chem. Phys. 2007, 9, 2630.
7. [7]
  (7) Wang, Z. S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara,K. J. Phys. Chem. C 2007, 111, 7224. doi: 10.1021/jp067872t
8. [8]
  (8) Chen, R.; Yang, X.; Tian, H.; Sun, L. J. Photochem. Photobiol.A: Chem. 2007, 189, 295. doi: 10.1016/j.jphotochem.2007.02.018
9. [9]
  (9) Tian, H.; Yang, X.; Chen, R.; Pan, Y.; Li, L.; Hagfeldt, A.; Sun,L. Chem. Commun. 2007, 3741.
10. [10]
  (10) Kim, S.; Kim, D.; Choi, H.; Kang, M. S.; Song, K.; Kang, S. O.;Ko, J. Chem. Commun. 2008, 4951.
11. [11]
  (11) Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska,P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun. 2008,5194.
12. [12]
  (12) Li, C.; Yum, J. H.; Moon, S. J.; Herrmann, A.; Eickemeyer, F.;Pschirer, N. G.; Erk, P.; Schöneboom, J.; Müllen, K.; Grätzel,M.; Nazeeruddin, M. K. ChemSusChem 2008, 1, 615. doi: 10.1002/cssc.v1:7
13. [13]
  (13) Jin, Y.; Hua, J.;Wu,W.; Ma, X.; Meng, F. Synth. Met. 2008,158, 64.
14. [14]
  (14) Burke, A.; Ito, S.; Snaith, H.; Bach, U.; Kwiatkowski, J.; andGrtzel, M. Nano lett. 2008, 8, 977. doi: 10.1021/nl071588b
15. [15]
  (15) Chen, Z.; Li, F.; Huang, C. H. Curr. Org. Chem. 2007, 11, 1241.doi: 10.2174/138527207781696008
16. [16]
  (16) Rochford, J.; Chu, D.; Hagfeldt, A.; Galoppini, E. J. Am. Chem.Soc. 2007, 129, 4655. doi: 10.1021/ja068218u
17. [17]
  (17) Tsai, M. S.; Hsu, Y. C.; Lin, J. T.; Chen, H. C.; Hsu, C. P.J. Phys. Chem. C 2007, 111, 18785. doi: 10.1021/jp075653h
18. [18]
  (18) Chen, R.; Yang, X.; Tian, H.;Wang, X.; Hagfeldt, A.; Sun, L. C.Chem. Mater. 2007, 19, 4007 doi: 10.1021/cm070617g
19. [19]
  (19) Choi, H.; Lee, J. K.; Song, K. H.; Song, K.; Kang, S. O.; Ko, J.Tetrahedron 2007, 63, 1553. doi: 10.1016/j.tet.2006.12.013
20. [20]
  (20) Park, J. K.; Lee, H. R.; Chen, J.; Shinokubo, H.; Osuka, A.;Kim, D. J. Phys. Chem. C 2008, 112, 16691. doi: 10.1021/jp804258q
21. [21]
  (21) Eu, S. H.; Hayashi, S.; Umeyama, T.; Matano, Y.; Araki, Y.;Imahori, H. J. Phys. Chem. C 2008, 112, 4396. doi: 10.1021/jp710400p
22. [22]
  (22) Yen, Y. S.; Hsu, Y. C.; Lin, J. T.; Chang, C.W.; Hsu, C. P.; Yin,D. J. J. Phys. Chem. C 2008, 112, 12557. doi: 10.1021/jp801036s
23. [23]
  (23) Li, G.; Jiang, K. J.; Li, Y. F.; Li, S. L.; Yang, L. M. J. Phys.Chem. C 2008, 112, 11591. doi: 10.1021/jp802436v
24. [24]
  (24) Balanay, M. P.; Kim, D. H. Phys. Chem. Chem. Phys. 2008, 10,5121.
25. [25]
  (25) Ooyama, Y.; Harima, Y. Eur. J. Org. Chem. 2009, 18, 2903.
26. [26]
  (26) Marinado, T.; Hagberg, D. P.; Hedlund, M.; Edvinsson, T.;Johansson, E. M. J.; Boschloo, G.; Rensmo, H.; Brinck, T.; Sun,L. C.; Hagfeldty, A. Phys. Chem. Chem. Phys. 2009, 11, 133.
27. [27]
  (27) Kurashige, Y.; Nakajima, T.; Kurashige, S.; Hirao, K.;Nishikitani, Y. J. Phys. Chem. A 2007, 111, 5544. doi: 10.1021/jp0720688
28. [28]
  (28) Zhang, X.; Zhang, J. J.; Xia, Y. Y. J. Photochem. Photobiol. A:Chem. 2008, 194, 167. doi: 10.1016/j.jphotochem.2007.08.004
29. [29]
  (29) Sayama, K.; Tsuka shi, S.; Mori, T.; Hara, K.; Ohga, Y.;Shinpo, A.; Abe, Y.; Suga, S.; Arakawa, H. Sol. Energy Mater.Sol. Cells 2003, 80, 47. doi: 10.1016/S0927-0248(03)00113-2
30. [30]
  (30) Zhao, G. J.; Chen, R. K.; Sun, M. T.; Liu, J. Y.; Li, G. Y.; Gao,Y. L.; Han, K. L.; Yang, X. C.; Sun, L. C. Chem. Eur. J. 2008,14, 6935. doi: 10.1002/chem.v14:23
31. [31]
  (31) Zhao, G. J.; Liu, J. Y.; Zhou, L. C.; Han, K. L. J. Phys. Chem. B2007, 111, 8940. doi: 10.1021/jp0734530
32. [32]
  (32) Zhao, G. J.; Han, K. L. Biophys. J. 2008, 94, 38. doi: 10.1529/biophysj.107.113738
33. [33]
  (33) Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.;Hagfeldt, A.; Sun, L. C. Chem. Commun. 2006, 2245.
34. [34]
  (34) Hagberg, D. P.; Yum, J. H.; Lee, H.; Angelis, F. D.; Marinado,T.; Karlsson, K. M.; Humphry-Baker, R.; Sun, L.; Hagfeldt, A.;Grätzel, M.; Nazeeruddin, M. K. J. Am. Chem. Soc. 2008, 130,6259. doi: 10.1021/ja800066y
35. [35]
  (35) Zhang, C. R.; Liu, Z. J.; Chen, Y. H.; Chen, H. S.;Wu, Y. Z.;Yuan, L. H. J. Mol. Struct. -Theochem 2009, 899, 86. doi: 10.1016/j.theochem.2008.12.015
36. [36]
  (36) Boschloo, G.; Marinado, T.; Nonomura, K.; Edvinsson, T.;Agrios, A. G.; Hagberg, D. P.; Sun, L. C.; Quintana, M.;Karthikeyan, C. S.; Thelakkat, M.; Hagfeldt, A. Thin SolidFilms 2008, 516, 7214. doi: 10.1016/j.tsf.2007.12.035
37. [37]
  (37) Agrios, A. G.; Hagfeldt, A. J. Phys. Chem. C 2008, 112, 10021.doi: 10.1021/jp800900x
38. [38]
  (38) Lin, J. T.; Chen, P. C.; Yen, Y. S.; Hsu, Y. C.; Chou, H. H.; Yeh,M. C. P. Organic Letters 2009, 11, 97. doi: 10.1021/ol8025236
39. [39]
  (39) De Angelis, F.; Fantacci, S.; Selloni, A.; Nazeeruddin, M. K.Chem. Phys. Lett. 2005, 415, 115. doi: 10.1016/j.cplett.2005.08.044
40. [40]
  (40) Xu, Y.; Chen,W. K.; Cao, M. J.; Liu, S. H.; Li, J. Q.;Philippopoulos, A. I.; Falaras, P. Chem. Phys. 2006, 330, 204.doi: 10.1016/j.chemphys.2006.08.012
41. [41]
  (41) Sun, J.; Song, J.; Zhao, Y.; Liang,W. Z. J. Chem. Phys. 2007,127, 234107. doi: 10.1063/1.2805396
42. [42]
  (42) Wang, Y. L.;Wu, G. S. Acta Phys. -Chim. Sin. 2008, 24, 552.[王溢磊, 吴国是. 物理化学学报, 2008, 24, 552.] doi: 10.1016/S1872-1508(08)60021-2
43. [43]
  (43) Li, H. X.; Pan, S. J.;Wang, X. F.; Xiao, T. Chin. J. Chem. Phys.2008, 21, 263. doi: 10.1088/1674-0068/21/03/263-269
44. [44]
  (44) Zhang, C. R.;Wu, Y. Z.; Chen, Y. H.; Chen, H. S. ActaPhys. -Chim. Sin. 2009, 25, 53. [张材荣, 吴有智, 陈玉红,陈宏善. 物理化学学报, 2009, 25, 53.] doi: 10.3866/PKU.WHXB20090110
45. [45]
  (45) Zhan,W. S.; Pan, S.; Li, Y. Z.; Chen, M. D. Acta Phys. -Chim.Sin. 2009, 25, 2087. [詹卫伸, 潘石, 李源作, 陈茂笃. 物理化学学报, 2009, 25, 2087.] doi: 10.3866/PKU.WHXB20090925
46. [46]
  (46) Zhan,W. S.; Pan, S.;Wang, Q.; Li, H.; Zhang, Y. ActaPhys. -Chim. Sin. 2012, 28, 78. [詹卫伸, 潘石, 王乔,李宏, 张毅. 物理化学学报, 2012, 28, 78.] doi: 10.3866/PKU.WHXB20122878
47. [47]
  (47) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B. et al. Gaussian 03,Revision C.02; Gaussian Inc: Pittsburgh, PA, 2003.
48. [48]
  (48) Becke, A. D. J. Chem. Phys. 1993, 98, 1372. doi: 10.1063/1.464304
49. [49]
  (49) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
50. [50]
  (50) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J.J. Phys. Chem. 1994, 98, 11623. doi: 10.1021/j100096a001
51. [51]
  (51) Bene, J. E. D.; Person,W. B.; Szczepaniak, K. J. Phys. Chem.1995, 99, 10705. doi: 10.1021/j100027a005
52. [52]
  (52) Hertwig, R. H.; Koch,W. Chem. Phys. Lett. 1997, 268, 345. doi: 10.1016/S0009-2614(97)00207-8
53. [53]
  (53) Tozer, D. J.; Handy, N. C. J. Chem. Phys. 1998, 109, 10180. doi: 10.1063/1.477711
54. [54]
  (54) Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393,51. doi: 10.1016/j.cplett.2004.06.011
55. [55]
  (55) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995. doi: 10.1021/jp9716997
56. [56]
  (56) Klamt, A. J. Phys. Chem. 1995, 99, 2224. doi: 10.1021/j100007a062
57. [57]
  (57) Klamt, A. J. Phys. Chem. 1996, 100, 3349. doi: 10.1021/jp950607f
58. [58]
  (58) Reed, A. E.;Weinstock, R. B.;Weinhold, F. J. Chem. Phys.1985, 83, 735. doi: 10.1063/1.449486
59. [59]
  (59) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem.2003, 24, 669. doi: 10.1002/jcc.10189
1. [1]
  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
2. [2]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
3. [3]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
4. [4]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
5. [5]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
6. [6]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
7. [7]
  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
8. [8]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
9. [9]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
10. [10]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
11. [11]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
12. [12]
  Yipeng Zhou , Chenxin Ran , Zhongbin Wu . Metacognitive Enhancement in Diversifying Ideological and Political Education within Graduate Course: A Case Study on “Solar Cell Performance Enhancement Technology”. University Chemistry, 2024, 39(6): 151-159. doi: 10.3866/PKU.DXHX202312096
13. [13]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
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]
  Yixuan Gao , Lingxing Zan , Wenlin Zhang , Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091
16. [16]
  Pengyu Dong , Yue Jiang , Zhengchi Yang , Licheng Liu , Gu Li , Xinyang Wen , Zhen Wang , Xinbo Shi , Guofu Zhou , Jun-Ming Liu , Jinwei Gao . NbSe₂纳米片优化钙钛矿太阳能电池的埋底界面. Acta Physico-Chimica Sinica, 2025, 41(3): 2407025-. doi: 10.3866/PKU.WHXB202407025
17. [17]
  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
18. [18]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
19. [19]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
20. [20]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007

Get Citation

PDF

XML

Metrics

PDF Downloads(763)
Abstract views(1579)
HTML views(8)

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