Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Characterization of Peripherally Ferrocene-modified Zinc Phthalocyanine for Dye-sensitized Solar Cell

  • An, Min-Shi (Department of Chemistry, University of Incheon) ;
  • Kim, Soon-Wha (Department of Chemistry, University of Incheon) ;
  • Hong, Jong-Dal (Department of Chemistry, University of Incheon)
  • Received : 2010.07.12
  • Accepted : 2010.09.14
  • Published : 2010.11.20
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Abstract

Synthesis and structural characterization of peripherally ferrocene-substituted zinc phthalocyanine (ZnPc-Fc) were carried out for efficient far-red/near-IR performance in dye-sensitized nanostructured $TiO_2$ solar cells. Incorporating ferrocene into phthalocyanine strongly improved the dye solubility in polar organic solvents, and reduced surface aggregation due to the steric effect of bulky ferrocene substituents. The involvement of electron transfer reaction pathways between ferrocene and phthalocyanine in ZnPc-Fc was evidenced by completely quenched fluorescence from S1 state (< 0.08% vs ZnPc). Strong absorption bands at 542 and 682 nm were observed in the transient absorption spectroscopy of ZnPc-Fc in DMSO, which was excited at a 670 nm laser pulse with a 15 ps full width at half maximum. Also, the excited state absorption signals at 450 - 600 and 750 - 850 nm appeared from the formation of charge separated state of phthalocyanine's anion. The lifetime of the charge separate state in ZnPc-Fc was determined to be $170{\pm}8$ ps, which was almost 17 times shorter than that of the ZnPc.

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References

  1. Regan, B. O’.; Gratzel, M. Nature 1991, 353,737. https://doi.org/10.1038/353737a0
  2. Nazeeruddin, M. K.; De Angelis, F.; Fantacci, S.; Selloni, A.; Viscardi, G.; Liska, P.; Ito, S.; Bessho, T.; Grätzel, M. J. Am. Chem. Soc. 2005, 127, 16835. https://doi.org/10.1021/ja052467l
  3. Leznoff, C. C., Lever, A. B. P., Eds.; Phthalocyanines: Properties and Applications; VCH: New York, 1993; Vol. 1, 1993; Vol. 2, 1993; Vol. 3, 1996; Vol. 4.
  4. Kamat, P. V. Chem. Rev. 1993, 93, 267. https://doi.org/10.1021/cr00017a013
  5. Gritzner, G.; Kuta, J. J. Pure. Appl. Chem. 1984, 56, 461. https://doi.org/10.1351/pac198456040461
  6. He, J.; Benko, G.; Korodi, F.; Polivka, T.; Lomoth, R.; Okermark, B.; Sun, L.; Hagfeldt, A.; Sundstrom, V. J. Am. Chem. Soc. 2002, 124, 4922. https://doi.org/10.1021/ja0178012
  7. Cid, J. J.; Yum, J. H.; Jang, S. R.; Nazeeruddin, M. K.; Martnez-Ferrero, E.; Palomares, E.; Ko, J.; Gratzel, M.; Torres, T. Angew. Chem. Int. Ed. 2007, 46, 8358. https://doi.org/10.1002/anie.200703106
  8. Seiwert, B.; Karst, U. Anal. Bioanal. Chem. 2008, 390, 181. https://doi.org/10.1007/s00216-007-1639-7
  9. Schlettwein, D.; Oekermann, T.; Yoshida, T.; Tochimoto, M.; Minoura, H. J. Electroanal. Chem. 2000, 481, 42. https://doi.org/10.1016/S0022-0728(99)00475-1
  10. Nevin, W. A.; Liu, W.; Lever, A. B. P. Can. J. Chem. 1987, 65, 855. https://doi.org/10.1139/v87-144
  11. Snow, A. W.; Jarvis, N. L. J. Am. Chem. Soc. 1984, 106, 4706. https://doi.org/10.1021/ja00329a012
  12. Schutte, W. J.; Sluyters-Rehbach, M.; Sluyters, J. H. J. Phys. Chem. 1993, 97, 6069.
  13. He, J.; Hagfeldt, A.; Lindquist, S.-E.; Grennberg, H.; Korodi, F.; Sun, L.; Okermark, B. Langmuir 2001, 17, 2743. https://doi.org/10.1021/la001651b
  14. Kazuya, K.; Mitsuhiko, M.; Akiharu, S.; Yoshiaki, K. Angew. Chem. 2005, 117, 4841. https://doi.org/10.1002/ange.200501199
  15. 5Zhou, Y.; Wang, Z.; Sugiura, K.; Sakata, Y. J. Journal of Porphyrins and Phthalocyanines 2001, 5, 523. https://doi.org/10.1002/jpp.358
  16. Kobayashi, N.; Lever, A. B. P. J. Am. Chem. Soc. 1987, 109, 7433. https://doi.org/10.1021/ja00258a030
  17. Kubo, M.; Mori, Y.; Otani, M.; Murakami, M.; Ishibashi, Y.; Yasuda, M.; Hosomizu, K.; Miyasaka, H.; Imahori, H.; Nakashima, S. J. Phys. Chem. A 2007, 111, 5136. https://doi.org/10.1021/jp071546b
  18. Shen, Y.; Wang, L.; Lu, Z.; Wei, Y.; Zhou, Q.; Mao, H.; Xu, H. Thin Solid Films 1995, 257, 144. https://doi.org/10.1016/0040-6090(94)06329-X
  19. Yanagi, H.; Chen, S.; Lee, P. A.; Nebesny, K. W.; Armstrong, N. R.; Fujishima, A. J. Phys. Chem. 1996, 100, 5447. https://doi.org/10.1021/jp952733p
  20. Schneider, G.; Wöhrle, D.; Spiller, W.; Stark, J.; Schulz-Ekloff, G. Photochem. Photobiol. 1994, 60, 333. https://doi.org/10.1111/j.1751-1097.1994.tb05112.x
  21. Spiller, W.; Kliesch, H.; Wöhrle, D.; Hackbarth, S.; Roeder, B. J. Porphyrins. Phthalocyanines 1998, 2, 145. https://doi.org/10.1002/(SICI)1099-1409(199803/04)2:2<145::AID-JPP60>3.0.CO;2-2
  22. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995.
  23. Rodgers, M. A. J. Photosensitization; Moreno, G. R., Pottier, H. T., Truscott, G., Eds.; Springer: Berlin, 1988.
  24. Hwang, I.-W.; Kamada, T.; Ahn, T. K.; Ko, D. M.; Nakamura, T.; Tsuda, A.; Osuka, A.; Kim, D. J. Am. Chem. Soc. 2004, 126, 16187. https://doi.org/10.1021/ja046241e

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  14. Ferrocenyl Phthalocyanine as Donor in Non-Poly(3-hexylthiophen-2,5-diyl) Bulk Heterojunction Solar Cell vol.24, pp.27, 2018, https://doi.org/10.1002/chem.201801340
  15. Synthesis, characterization and electrochemistry of novel unsymmetrical zinc phthalocyanines sensitizer with extended conjugation vol.1022, pp.None, 2010, https://doi.org/10.1016/j.molstruc.2012.04.046
  16. Electrolyte-Free Dye-Sensitized Solar Cell with High Open Circuit Voltage Using a Bifunctional Ferrocene-Based Cyanovinyl Molecule as Dye and Redox Couple vol.37, pp.13, 2010, https://doi.org/10.1021/acs.organomet.8b00104