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Time-resolved fluorescence of α,ω-di(1-naphthyl)oligosilanes and 1-naphthyloligosilanes: intramolecular excimer formation and charge-transfer interactions

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Abstract

The intramolecular photochemical processes excimer formation and charge-transfer (CT) complex formation were investigated by comparing the behavior of α,ω-di(1-naphthyl)permethyloligosilanes ((1-naphthyl)-(SiMe2) n -(1-naphthyl); NS n N, n = 1, 3, and 6) and 1-(1-naphthyl)permethyloligosilanes ((1-naphthyl)-(SiMe2) n -Me; NS n, n = 1, 3, and 6) by use of stationary and time-resolved fluorescence (TR-FL) measurements. Formation of excimer and CT complexes is highly dependent on the silicon chain length and polarity of the medium.

Graphical Abstract

Intramolecular excimer formation between the two naphthyl groups and charge transfer interactions between the naphthyl and silane moieties were investigated by use of a time-correlated single-photon counting method.

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References

  1. H. Maeda, H. Yagi, K. Mizuno, Chem. Lett. 33, 388 (2004)

    Article  CAS  Google Scholar 

  2. H. Maeda, K. Nishimura, K. Mizuno, M. Yamaji, J. Oshima, S. Tobita, J. Org. Chem. 70, 9693 (2005)

    Article  CAS  Google Scholar 

  3. H. Shizuka, Y. Sato, Y. Ueki, M. Ishikawa, M. Kumada, J. Chem. Soc. Faraday Trans. 1 80, 341 (1984)

    Article  CAS  Google Scholar 

  4. H. Shizuka, H. Obuchi, M. Ishikawa, M. Kumada, J. Chem. Soc. Faraday Trans. 1 80, 383 (1984)

    Article  CAS  Google Scholar 

  5. M. Kira, T. Miyazawa, H. Sugiyama, M. Yamaguchi, H. Sakurai, J. Am. Chem. Soc. 115, 3116 (1993)

    Article  CAS  Google Scholar 

  6. C.G. Pitt, R.N. Carey, E.C. Toren Jr, J. Am. Chem. Soc. 94, 3806 (1972)

    Article  CAS  Google Scholar 

  7. H. Tsuji, Y. Shibano, T. Takahashi, M. Kumada, K. Tamao, Bull. Chem. Soc. Jpn. 78, 1334 (2005)

    Article  CAS  Google Scholar 

  8. D. Declercq, P. Delbeke, F.C. de Schryver, L.V. Meervelt, R.D. Miller, J. Am. Chem. Soc. 115, 5702 (1993)

    Article  CAS  Google Scholar 

  9. D. Declercq, F.C. de Schryver, R.D. Miller, Chem. Phys. Lett. 186, 467 (1991)

    Article  CAS  Google Scholar 

  10. T. Karatsu, T. Shibata, A. Nishigaki, K. Fukui, A. Kitamura, Chem. Lett. 30, 994 (2001)

    Article  Google Scholar 

  11. T. Karatsu, T. Shibata, A. Nishigaki, A. Kitamura, Y. Hatanaka, Y. Nishimura, S. Sato, I. Yamazaki, J. Phys. Chem. B 107, 12184 (2003)

    Article  CAS  Google Scholar 

  12. F. Hirayama, J. Chem. Phys. 42, 3163 (1965)

    Article  CAS  Google Scholar 

  13. K. Takahashi, Y. Nishimura, T. Arai, S. Yagai, A. Kitamura, T. Karatsu, J. Photochem. Photobiol. A 218, 204 (2011)

    Article  CAS  Google Scholar 

  14. H. Bouras-Laurent, J.-P. Desvergne, in Photochromism, ed. by H. Dürr, H. Bouras-Laurent (Elsevier, Amsterdam 1990), pp. 561–630, and cited therein

  15. H.-D. Becker, in Advances in photochemistry, vol. 15, ed. by D.H. Volman, G.S. Hammond, K. Gollnick (Wiley, New York, 1990), pp. 139–227

    Chapter  Google Scholar 

  16. H. Sakurai, K. Sakamoto, A. Nakadaira, M. Kira, Chem. Lett. 14, 497 (1985)

    Article  Google Scholar 

  17. M. Daney, C. Vanucci, J.-P. Desvergne, A. Castellan, H. Bouas-Laurent, Tetrahedron Lett. 26, 1505 (1985)

    Article  CAS  Google Scholar 

  18. K. Takahashi, Y. Takanashi, S. Yagai, A. Kitamura, T. Karatsu, J. Photopolym. Sci. Technol. 23, 789 (2010)

    Article  CAS  Google Scholar 

  19. Y. Nishimura, A. Yasuda, S. Speiser, I. Yamazaki, Chem. Phys. Lett. 323, 117 (2000)

    Article  CAS  Google Scholar 

  20. M. Hasegawa, S. Enomoto, T. Hoshi, K. Igarashi, T. Yamazaki, Y. Nishimura, S. Speiser, I. Yamazaki, J. Phys. Chem. B 106, 4925 (2002)

    Article  CAS  Google Scholar 

  21. S. Speiser, Chem. Rev. 96, 1953 (1996)

    Article  CAS  Google Scholar 

  22. T. Karatsu, M. Terasawa, S. Yagai, A. Kitamura, T. Nakamura, Y. Nishimura, I. Yamazaki, J. Organomet. Chem. 689, 1029 (2004)

    Article  CAS  Google Scholar 

  23. M. Kumada, M. Yamaguchi, Y. Yamamoto, J. Nakajima, K. Shiina, J. Org. Chem. 21, 1264 (1956)

    Article  CAS  Google Scholar 

  24. H. Gilman, S. Inoue, J. Org. Chem. 29, 3418 (1964)

    Article  CAS  Google Scholar 

  25. T. Hayashi, N. Mataga, Y. Sakata, S. Misumi, M. Morita, J. Tanaka, J. Am. Chem. Soc. 98, 5910 (1976)

    Article  CAS  Google Scholar 

  26. A.G. Evans, B. Jerome, N.H. Rees, J. Chem. Soc. Perkin Trans 2, 447 (1973)

    Google Scholar 

  27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.11.4 (Gaussian Inc., Pittsburgh, 1998)

  28. M.K. Raymond, J. Michl, Int. J. Quantum Chem. 72, 361 (1999)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (no. 20550056), Scientific Research on Priority Areas (417, no. 17029013), and the G-COE program from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of the Japanese Government and the COE start-up program from Chiba University.

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Author notes

  1. Yoshinobu Nishimura

    Present address: Department of Chemistry, University of Tsukuba, Tsukuba, Japan

Authors and Affiliations

  1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan

    Takashi Karatsu, Masato Terasawa, Shiki Yagai & Akihide Kitamura

  2. Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan

    Takashi Nakamura, Yoshinobu Nishimura & Iwao Yamazaki

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  1. Takashi Karatsu
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  2. Takashi Nakamura
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  6. Yoshinobu Nishimura
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Correspondence to Takashi Karatsu.

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Dedicated to Professor Kazuhiko Mizuno on his retirement from Osaka Prefecture University.

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Karatsu, T., Nakamura, T., Terasawa, M. et al. Time-resolved fluorescence of α,ω-di(1-naphthyl)oligosilanes and 1-naphthyloligosilanes: intramolecular excimer formation and charge-transfer interactions. Res Chem Intermed 39, 347–357 (2013). https://doi.org/10.1007/s11164-012-0653-3

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  • DOI: https://doi.org/10.1007/s11164-012-0653-3

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