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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 04: 815 - 819

DOI: https://doi.org/10.6023/cjoc201301059

Articles

Photophysical and Electrochemical Studies of Porphyrin Containing Ferrocene and/or Fluorine

  • Su Min ,
  • Li Qing ,
  • Wang Yaguang ,
  • Chen Shufeng ,
  • Zhao Haiying ,
  • Bian Zhanxi
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  • College of Chemistry and Chemical Engineering, Inner Mongolia University, Huhhot 010021

Received date: 2013-01-24

  Revised date: 2013-03-14

  Online published: 2013-03-22

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21102068, 21262023).

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Abstract

Functionalized porphyrin and porphyrin containing trifluoromethyl with ferrocene were synthesized. The UV-Vis absorption bands of porphyrin with an electron withdrawing trifluoromethyl group were blue-shifted and those of porphyrin with an electron donating ferrocenyl group were red-shifted. The porphyrin containing ferrocenyl exhibited strong fluorescence quenching compared with those containing trifluoromethyl. The quenching efficiency of diferrocenyl porphyrin was about 66% with a quantum yield Φf of 0.08. These results indicated that there was a strong interaction between the excited state of porphyrin and ferrocene, which was further confirmed by the time-resolved fluorescence measurements. The electrochemical studies indicated that it was difficult to lost electron for the stable porphyrin with an electron withdrawing trifluoromethyl. However, the porphyrin with a ferrocenyl group was oxidized easily to lost electron and was a good electron donor. The research is supposed to provide some theoretical basis for this kind of compound using in donor-acceptor system.

Key words： ferrocene; porphyrin containing fluorine; spectroscopic property; electrochemistry

Cite this article

Su Min , Li Qing , Wang Yaguang , Chen Shufeng , Zhao Haiying , Bian Zhanxi . Photophysical and Electrochemical Studies of Porphyrin Containing Ferrocene and/or Fluorine[J]. Chinese Journal of Organic Chemistry, 2013 , 33(04) : 815 -819 . DOI: 10.6023/cjoc201301059

References

[1] Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Ehli, C. Chem. Soc. Rev. 2006, 35, 471.

[2] Fungo, F.; Milanesio, M. E.; Durantini, E. N.; Otero, L.; Dittrich, T. J. Mater. Chem. 2007, 17, 2107.

[3] Straight, S. D.; Andréasson, J.; Kodis, G.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 2005, 127, 2717.

[4] Fukuzumi, S.; Kojima, T. J. Mater. Chem. 2008, 18, 1427.

[5] Imahori, H.; Sekiguchi, Y.; Kashiwagi, Y.; Sato, T.; Araki, Y.; Ito, O.; Yamada, H.; Fukuzumi, S. Chem. Eur. J. 2004, 10, 3184.

[6] D’Souza, F.; Gadde, S.; Islam, D. M. S.; Wijesinghe, C. A.; Schumacher, A. L.; Zandler, M. E.; Araki, Y.; Ito, O. J. Phys. Chem. A 2007, 111, 8552.

[7] Imahori, H.; Tamaki, K.; Yamada, H.; Yamada, K.; Sakata, Y.; Nishimura, Y.; Yamazaki, I.; Fujitsuka, M.; Ito, O. Carbon 2000, 38, 1599.

[8] Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2607.

[9] Zhao, H. Y.; Chen, C.; Zhu, Y. Z.; Shi, M. Z.; Zheng, J. Y. J. Nanopart. Res. 2012, DOI: 10.1007/s11051-012-0765-0.

[10] Zhao, H. Y.; Zhu, Y. Z.; Chen, C.; He, L.; Zheng, J. Y. Carbon 2012, 50, 4894.

[11] Galloni, P.; Floris, B.; Cola, L. D.; Cecchetto, E.; Williams, R. M. J. Phys. Chem. C 2007, 111, 1517.

[12] Samanta, S.; Sengupta, K.; Mittra, K.; Bandyopadhyay, S.; Dey, A. Chem. Commun. 2012, 48, 7631.

[13] Zhu, P.; Ma, P.; Wang, Y.; Wang, Q.; Zhao, X.; Zhang, X. Eur. J. Inorg. Chem. 2011, 4241.

[14] Rohde, G. T.; Sabin, J. R.; Barrett, C. D.; Nemykin, V. N. New J. Chem. 2011, 35, 1440.

[15] Zhou, X. L.; Kang, S. W.; Kumar, S.; Li, Q. Liq. Cryst. 2009, 36, 269.

[16] Sakurai, T.; Tashiro, K.; Honsho, Y.; Saeki, Akinori.; Seki, Shu.; Osuka, A.; Muranaka, A.; Uchiyama, M.; Kim, J.; Ha, S.; Kato, K.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2011, 133, 6537.

[17] Kim, E. H.; Kadkin, O. N.; Kim, S. Y.; Choi, M.-G. Eur. J. Inorg. Chem. 2011, 2933.

[18] Kim, S. Y.; Kadkin, O. N.; Kim, E. H.; Choi, M.-G. J. Organomet. Chem. 2011, 696, 2429.

[19] Bonar-Law, R. P. J. Org. Chem. 1996, 61, 3623.

[20] He, D.; Zhang, H.; Peng, Y.; Ma, D.; Wang, Y.; Yang, H.; Chen, W.; Zhang, T. Chin. J. Org. Chem. 2012, 32, 1320 (in Chinese).
(贺丹丹, 张宏, 彭亦如, 马冬冬, 王瑜华, 杨洪钦, 陈婉玲, 张甜甜, 有机化学, 2012, 32, 1320.)

[21] Ormond, A. B.; Freeman, H. S. Dyes Pigm. 2013, 96, 440.

[22] Xu, H.; Zhu, Y. Z.; Zheng, J. Y. Supramol. Chem. 2007, 19, 365.

[23] D'Souza, F.; Smith, P. M.; Gadde, S.; McCarty, A. L.; Kullman, M. J.; Zandler, M. E.; Itou, M.; Araki, Y.; Ito, O. J. Phys. Chem. B 2004, 108, 11333.
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