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

doi:10.1007/s40242-013-3084-9

Abstract

Abstract:

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.

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]. Chemical Research in Chinese Universities, 2013, 29(5): 974-981.

References

[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