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
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