Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells

doi:10.1007/s40242-013-3084-9

高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (5): 974-981.doi: 10.1007/s40242-013-3084-9

Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells

ZHAO Yi-dan¹, FU Jing-jing¹, LI Hai-bin¹, DONG Hao², LIAO Yi¹

1. Department of Chemistry, Capital Normal University, Beijing 100048, P. R. China;
2. Institute of Chemistry for Functionalized Material, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P. R. China

收稿日期:2013-03-04 修回日期:2013-05-10 出版日期:2013-10-01 发布日期:2013-09-17
通讯作者: DONG Hao, LIAO Yi E-mail:sinodonghao@gmail.com;liaoy271@nenu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.11179033), the Program for New Century Excellent Talents in University of China(No.NCET-10-0011), the Beijing Natural Science Foundation, China(No.2132017) and Program for the Top Young Talents of Higher Learning Institutions of Beijing Municipality China.

Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells

ZHAO Yi-dan¹, FU Jing-jing¹, LI Hai-bin¹, DONG Hao², LIAO Yi¹

1. Department of Chemistry, Capital Normal University, Beijing 100048, P. R. China;
2. Institute of Chemistry for Functionalized Material, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P. R. China

Received:2013-03-04 Revised:2013-05-10 Online:2013-10-01 Published:2013-09-17
Contact: DONG Hao, LIAO Yi E-mail:sinodonghao@gmail.com;liaoy271@nenu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.11179033), the Program for New Century Excellent Talents in University of China(No.NCET-10-0011), the Beijing Natural Science Foundation, China(No.2132017) and Program for the Top Young Talents of Higher Learning Institutions of Beijing Municipality China.

摘要/Abstract

摘要：

We studied the excitation energies of zinc porphyrin(ZnP) and zinc porphyrin analogues(ZnP-R) with long-range corrected(LC) density functional theory. We compared three recent LC functionals, wB97XD, CAM-B3LYP, LC-wPBE and functionals B3LYP with the experiments. It was found that the low energy excitation is well predicted for ZnP with the LC-wPBE functional based on 6-31G(d) basis set. Excited-state geometry optimizations for all the compounds were carried out. It was shown that upon the photo-excitation nearly 1 e transferred to the acceptor unit[dodecafluorosubphthalocyanine, SubPc(F)₁₂] and a highly polarized state formed in compound 5. But after the relaxation of the first excited state, the electron on the acceptor went back to the ZnP a little and then shifted from ZnP to the donor segment[bis(4-hexylphenyl)amino] partially. The computed excited-state radiative lifetime(τ) for compound 5 is 943 μs, which shows a reasonable agreement with the experimental observation. According to the long-lived exciton in strong push-pull compound 5, we proposed that electron injection to semiconductor might occur after vibrational relaxation of excited state.

关键词: Excitation energy, Long-range corrected(LC) functional, Zinc porphyrin, Zinc porphyrin analogue, Electron injection

Abstract:

Key words: Excitation energy, Long-range corrected(LC) functional, Zinc porphyrin, Zinc porphyrin analogue, Electron injection

ZHAO Yi-dan, FU Jing-jing, LI Hai-bin, DONG Hao, LIAO Yi. Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells[J]. 高等学校化学研究, 2013, 29(5): 974-981.

ZHAO Yi-dan, FU Jing-jing, LI Hai-bin, DONG Hao, LIAO Yi. Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells[J]. Chemical Research in Chinese Universities, 2013, 29(5): 974-981.

参考文献

[1] Oregan B., Gratzel M., Nature, 1991, 353(6346), 737
[2] Nazeeruddin M. K., Kay A., Rodicio I., Humphrybaker R., Muller E., Liska P., Vlachopoulos N., Gratzel M., J. Am. Chem. Soc., 1993, 115(14), 6382
[3] Gratzel M., Inorg. Chem., 2005, 44(20), 6841
[4] Chiba Y., Islam A., Watanabe Y., Komiya R., Koide N., Han L. Y., Japanese Journal of Applied Physics Part 2: Letters & Express Letters, 2006, 45(24―28), L638
[5] Zhang Y. H., Zhao W., Jiang P., Zhang L. J., Zhang T., Wang J., Spectrochim Acta A: Mol. Biomol. Spectrosc., 2010, 75(2), 880
[6] Campbell W. M., Burrell A. K., Officer D. L., Jolley K. W., Coordination Chemistry Reviews, 2004, 248(13/14), 1363
[7] Hara K., Wang Z. S., Sato T., Furube A., Katoh R., Sugihara H., Dan-Oh Y., Kasada C., Shinpo A., Suga S., J. Phys. Chem. B, 2005, 109(32), 15476
[8] Walzer K., Maennig B., Pfeiffer M., Leo K., Chemical Reviews, 2007, 107(4), 1233
[9] Nazeeruddin M. K., Humphry-Baker R., Officer D. L., Campbell W. M., Burrell A. K., Gratzel M., Langmuir, 2004, 20(15), 6514
[10] Schmidt-Mende L., Campbell W. M., Wang Q., Jolley K. W., Officer D. L., Nazeeruddin M. K., Gratzel M., Chemphyschem, 2005, 6(7), 1253
[11] Campbell W. M., Jolley K. W., Wagner P., Wagner K., Walsh P. J., Gordon K. C., Schmidt-Mende L., Nazeeruddin M. K., Wang Q., Gratzel M., Officer D. L., J. Phys. Chem. C, 2007, 111(32), 11760
[12] Barone V., Polimeno A., Chemical Society Reviews, 2007, 36, 1724
[13] Walsh P. J., Gordon K. C., Wagner P., Officer D. L., Chemphyschem, 2006, 7(11), 2358
[14] Walsh P. J., Gordon K. C., Officer D. L., Campbell W. M., J. Mole. Struct.(Theochem.), 2006, 759(1—3), 17
[15] Balanay M. P., Dipaling C. V. P., Lee S. H., Kim D. H., Lee K. H., Solar Energy Materials and Solar Cells, 2007, 91(19), 1775
[16] Balanay M. P., Kim D. H., Phys. Chem. Chem. Phys., 2008, 10(33), 5121
[17] Mozer A. J., Wagner P., Officer D. L., Wallace G. G., Campbell W. M., Miyashita M., Sunahara K., Mori S., Chem. Commun., 2008,(39), 4741
[18] Bessho T., Zakeeruddin S. M., Yeh C. Y., Diau E. W. G., Gratzel M., Angew. Chem. Int. Ed., 2010, 49(37), 6646
[19] Lind S. J., Gordon K. C., Gambhir S., Officer D. L., Phys. Chem. Chem. Phys., 2009, 11(27), 5598
[20] Huang X. B., Shi Q. Q., Chen W. Q., Zhu C. L., Zhou W. Y., Zhao Z., Duan X. M., Zhan X. W., Macromolecules, 2010, 43(23), 9620
[21] Hagberg D. P., Edvinsson T., Marinado T., Boschloo G., Hagfeldt A., Sun L., Chem. Commun.(Camb), 2006,(21), 2245
[22] Dos Santos T., Morandeira A., Koops S., Mozer A. J., Tsekouras G., Dong Y., Wagner P., Wallace G., Earles J. C., Gordon K. C., Officer D., Durrant J. R., J. Phys. Chem. C, 2010, 114(7), 3276
[23] Fujitsuka M., Shimakoshi H., Hisaeda Y., Majima T., Journal of Photochemistry and Photobiology A: Chemistry, 2011, 217(1), 242
[24] Chokbunpiam T., Thamyongkit P., Saengsawang O., Hannongbua S., International Journal of Photoenergy, 2010, 492313
[25] Lopez R., Menendez M. I., Santander-Nelli M., Cardenas-Jiron G. I., Theoretical Chemistry Accounts, 2010, 127(5/6), 475
[26] El-Khouly M. E., Phys. Chem. Chem. Phys., 2010, 12(39), 12746
[27] Ma R. M., Guo P., Yang L. L., Guo L. S., Zeng Q. H., Liu G. Q., Zhang X. X., J. Mole. Struct.(Theochem.), 2010, 942(1―3), 131
[28] Ma R. M., Guo P., Yang L. L., Guo L. S., Zhang X. X., Nazeeruddin M. K., Gratzel M., J. Phys. Chem. A, 2010, 114(4), 1973
[29] Ren X. F., Ren A. M., Wang Q., Feng J. K., Acta Physico-Chimica Sinica, 2010, 26(1), 110
[30] Earles J. C., Gordon K. C., Stephenson A. W. I., Partridge A. C., Officer D. L., Phys. Chem. Chem. Phys., 2011, 13(4), 1597
[31] Dreuw A., Head-Gordon M., J. Am. Chem. Soc., 2004, 126(12), 4007
[32] Wodrich M. D., Corminboeuf C., Schreiner P. R., Fokin A. A., Schleyer P. V., Organic Letters, 2007, 9(10), 1851
[33] Tawada Y., Tsuneda T., Yanagisawa S., Yanai T., Hirao K., J. Chem. Phys., 2004, 120(18), 8425
[34] Kamiya M., Sekino H., Tsuneda T., Hirao K., J. Chem. Phys., 2005, 122(23), 234111
[35] Chiba M., Tsuneda T., Hirao K., J. Chem. Phys., 2006, 124(14), 144106
[36] Pastore M., Mosconi E., de Angelis F., Gratzel M., J. Phys. Chem. C, 2010, 114(15), 7205
[37] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision A.02, Gaussian Inc., Wallingford CT, 2009
[38] Becke A. D., Phys. Rev. A, 1988, 38(6), 3098
[39] Lee C. T., Yang W. T., Parr R. G., Phys. Rev. B, 1988, 37(2), 785
[40] Miehlich B., Savin A., Stoll H., Preuss H., Chem. Phys. Letters, 1989, 157(3), 200
[41] Vydrov O. A., Scuseria G. E., J. Chem. Phys., 2006, 125(23), 234109
[42] Vydrov O. A., Heyd J., Krukau A. V., Scuseria G. E., J. Chem. Phys., 2006, 125(7), 074106
[43] Vydrov O. A., Scuseria G. E., Perdew J. P., J. Chem. Phys., 2007, 126(15), 154109
[44] Yanai T., Tew D. P., Handy N. C., Chem. Phys. Lett., 2004, 393(1―3), 51
[45] Chai J. D., Head-Gordon M., Phys. Chem. Chem. Phys., 2008, 10(44), 6615
[46] Alessandro A., Norberto M., Chiara M., Filippo D. A., Edoardo M., Yum J. H., Zhang X. X., Mohammad K. N., Grätzel M., Energy & Environmental Science, 2009, 2(10), 1094
[47] Becke A. D., J. Chem. Phys., 1993, 98(2), 1372
[48] Adamo C., Barone V., J. Chem. Phys., 1999, 110(13), 6158
[49] Adamo C., Barone V., J. Chem. Phys., 1998, 108(2), 664
[50] Barone V., Cossi M., J. Phys. Chem. A, 1998, 102(11), 1995
[51] Ozarowski A., Lee H. M., Balch A. L., J. Am. Chem. Soc., 2003, 125(41), 12606
[52] Zhang Y. H., Zhao W., Jiang P., Zhang L. J., Zhang T., Wang J., Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2010, 75(2), 880
[53] Meyers F., Marder S. R., Pierce B. M., Bredas J. L., J. Am. Chem. Soc., 1994, 116(23), 10703
[54] Dogutan D. K., Ptaszek M., Lindsey J. S., J. Org. Chem., 2007, 72(13), 5008
[55] Labat F., Adamo C., J. Phys. Chem. C, 2007, 111(41), 15034
[56] Cahen D., Hodes G., Gratzel M., Guillemoles J. F., Riess I., J. Phys. Chem. B, 2000, 104(9), 2053
[57] Gouterman M., J. Chem. Phys., 1959, 30(5), 113
[58] Zyss J., Molecular Nonlinear Optics: Materials, Physics, and Devi- ces, Academic, Boston, 1993
[59] Moran A. M., Kelley A. M., Tretiak S., Chem. Phys. Lett., 2003, 367(3/4), 293
[60] Moser J. E., Gratzel M., Chimia, 1998, 52(4), 160
[61] Katoh R., Kasuya M., Kodate S., Furube A., Fuke N., Koide N., J. Phys. Chem. C, 2009, 113(48), 20738
[62] Katoh R., Furube A., Yoshihara T., Hara K., Fujihashi G., Takano S., Murata S., Arakawa H., Tachiya M., J. Phys. Chem. B, 2004, 108(15), 4818
[63] Kalyanasundaram K., Gratzel M., Coordination Chemistry Reviews, 1998, 177, 347
[64] Katoh R., Furube A., Hara K., Murata S., Sugihara H., Arakawa H., Tachiya M., J. Phys. Chem. B, 2002, 106(50), 12957
[65] Litani-Barzilai I., Bulatov V., Gridin V. V., Schechter I., Analytica Chimica Acta, 2004, 501(2), 151
[66] Chidthong R., Hannongbua S., Aquino A. J., Wolschann P., Lischka H., J. Comput. Chem., 2007, 28(10), 1735
[67] Lukes V., Aquino A., Lischka H., J. Phys. Chem. A, 2005, 109(45), 10232
[68] Lukes V., Aquino A. J., Lischka H., Kauffmann H. F., J. Phys. Chem. B, 2007, 111(28), 7954
[69] Meeto W., Suramitr S., Vannarat S., Hannongbua S., Chem. Phys., 2008, 349(1―3), 1
[70] El-Khouly M. E., Ryu J. B., Kay K. Y., Ito O., Fukuzumi S., J. Phys. Chem. C, 2009, 113(34), 15444

Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells

Photoinduced Charge Transfer Processes of Zinc Porphyrin Derivatives for Dye-sensitized Solar Cells

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