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Excited state intramolecular hydrogen atom transfer of phenylethynyl-substituted 2′-hydroxychalcones

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(E)-1-[2-Hydroxy-4-(phenylethynyl)phenyl]-3-[4-(phenylethynyl)phenyl]prop-2-en-1-one (1), (E)-1-[2-hydroxy-4-(phenylethynyl)phenyl]-3-phenylprop-2-en-1-one (2), and (E)-1-(2-hydroxyphenyl)-3-[4-(phenylethynyl)phenyl]prop-2-en-1-one (3), which belong to a new class of 2′-hydroxychalcones with phenylethynyl group(s) at the para position of the phenyl ring, were synthesized, and their photochemical properties were investigated. The lowest energy absorption band of 1 peaks at a longer wavelength (383 nm) with a much larger molar extinction coefficient (5.0 × 104 M −1 cm−1) than that of the parent 2′-hydroxychalcone (2′HC) (2.0 × 104 M −1 cm−1 at 318 nm). Upon photoexcitation, all three compounds underwent excited-state intramolecular hydrogen atom transfer (ESIHT) to produce an excited tautomer that emitted fluorescence with a large Stokes shift in the longer wavelength region at 600–700 nm. The quantum yield of the tautomer fluorescence of 1 was not high at 298 K (Φ f = 9.1 × 10−5), but was highest among 2′HC and its analogues. The Φ f values of 1–3 increased 10–30 fold upon reducing the temperature from 298 to 77 K.

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References

  1. R.S. Becker, W.F. Richey, J. Am. Chem. Soc. 89, 1298 (1967)

    Article  CAS  Google Scholar 

  2. M. Kasha, J. Chem. Soc., Faraday Trans. 2 82, 2379 (1986)

    Google Scholar 

  3. P.F. Barbara, P.K. Walsh, L.E. Brus, J. Phys. Chem. 93, 29 (1989)

    Article  CAS  Google Scholar 

  4. L.G. Arnaut, S.J. Formosinho, J. Photochem. Photobiol. A 75, 1 (1993)

    Article  CAS  Google Scholar 

  5. S.J. Formosinho, L.G. Arnaut, J. Photochem. Photobiol. A 75, 21 (1993)

    Article  CAS  Google Scholar 

  6. M. Kasha, J. Heldt, D. Gormin, J. Phys. Chem. 99, 7281 (1995)

    Article  CAS  Google Scholar 

  7. J. Catalán, J. Palomar, J.L.G. de Paz, J. Phys. Chem. A 101, 7914 (1997)

    Article  Google Scholar 

  8. W.-S. Yu, C.-C. Cheng, Y.-M. Cheng, P.-C. Wu, Y.-H. Song, Y. Chi, P.-T. Chou, J. Am. Chem. Soc. 125, 10800 (2003)

    Article  CAS  Google Scholar 

  9. A. Roque, C. Lodeiro, F. Pina, M. Maestri, R. Ballardini, V. Balzani, Eur. J. Org. Chem. 16, 2699 (2002)

    Article  Google Scholar 

  10. A. Ohshima, A. Momotake, T. Arai, J. Photochem. Photobiol. A 162, 473 (2004)

    Article  CAS  Google Scholar 

  11. A. Ohshima, A. Momotake, T. Arai, Chem. Lett. 34, 1288 (2005)

    Article  CAS  Google Scholar 

  12. A. Ohshima, A. Momotake, T. Arai, Bull. Chem. Soc. Jpn. 79, 305 (2006)

    Article  CAS  Google Scholar 

  13. A. Ohshima, A. Momotake, T. Arai, Tetrahedron Lett. 45, 9377 (2004)

    Article  CAS  Google Scholar 

  14. A. Ohshima, A. Momotake, R. Nagahata, T. Arai, J. Phys. Chem. A 109, 9731 (2005)

    Article  CAS  Google Scholar 

  15. A. Ohshima, M. Ikegami, Y. Shinohara, A. Momotake, T. Arai, Bull. Chem. Soc. Jpn. 80, 561 (2007)

    Article  CAS  Google Scholar 

  16. T. Kanda, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, T. Arai, Bull. Chem. Soc. Jpn. 82, 118 (2009)

    Article  CAS  Google Scholar 

  17. T. Iijima, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, T. Arai, J. Phys. Chem. A 114, 1603 (2010)

    Article  CAS  Google Scholar 

  18. T. Arai, M. Ikegami, Chem. Lett. 28, 965 (1999)

    Article  Google Scholar 

  19. M. Obi, H. Sakuragi, T. Arai, Chem. Lett. 27, 169 (1998)

    Article  Google Scholar 

  20. T. Arai, M. Moriyama, K. Tokumaru, J. Am. Chem. Soc. 116, 3171 (1994)

    Article  CAS  Google Scholar 

  21. F.D. Lewis, B.A. Yoon, T. Arai, T. Iwasaki, K. Tokumaru, J. Am. Chem. Soc. 117, 3029 (1995)

    Article  CAS  Google Scholar 

  22. T. Arai, M. Obi, T. Iwasaki, K. Tokumaru, F.D. Lewis, J. Photochem. Photobiol. A 96, 65 (1996)

    Article  CAS  Google Scholar 

  23. J.B. Harborne, Comparative Biochemistry of the Flavonoids (Academic Press, New York, 1967)

    Google Scholar 

  24. Z. Nowakowska, Eur. J. Med. Chem. 42, 125 (2007)

    Article  CAS  Google Scholar 

  25. P.-T. Chou, M.L. Martinez, W.C. Copper, J. Am. Chem. Soc. 114, 4943 (1992)

    Article  CAS  Google Scholar 

  26. T. Arai, Y. Norikane, Chem. Lett. 26, 339 (1997)

    Article  Google Scholar 

  27. Y. Norikane, H. Itoh, T. Arai, J. Phys. Chem. A 106, 2766 (2002)

    Article  CAS  Google Scholar 

  28. K. Tokumura, K. Nagaosa, Y. Ohta, R. Matsushima, Chem. Phys. Lett. 295, 516 (1998)

    Article  CAS  Google Scholar 

  29. K. Kaneda, T. Arai, Photochem. Photobiol. Sci. 2, 402 (2003)

    Article  CAS  Google Scholar 

  30. K. Kaneda, T. Arai, Org. Biomol. Chem. 1, 2041 (2003)

    Article  CAS  Google Scholar 

  31. K. Kaneda, S. Sato, H. Hamaguchi, T. Arai, Bull. Chem. Soc. Jpn. 77, 1529 (2004)

    Article  CAS  Google Scholar 

  32. T. Teshima, M. Takeishi, T. Arai, New J. Chem. 33, 1393 (2009)

    Article  CAS  Google Scholar 

  33. Y. Sugiyama, Y. Shinohara, A. Momotake, K. Takahashi, Y. Kanna, Y. Nishimura, T. Arai, J. Phys. Chem. A 114, 10929 (2010)

    Article  CAS  Google Scholar 

  34. W.H. Melhuish, J. Phys. Chem. 65, 229 (1961)

    Article  CAS  Google Scholar 

  35. K. Sonogashira, Y. Tohda, N. Hagiwara, Tetrahedron Lett. 50, 4467 (1975)

    Article  Google Scholar 

  36. Y. Amatatsu, M. Hosokawa, J. Phys. Chem. A 108, 10238 (2004)

    Article  CAS  Google Scholar 

  37. R. Matsushima, H. Kageyama, J. Chem. Soc. Perkin Trans. 2 6, 743 (1985)

  38. R. Matsushima, I. Hirao, Bull. Chem. Soc. Jpn. 53, 518 (1980)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research in a Priority Area “New Frontiers in Photochromism” (no. 471) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) and a Grant-in-Aid for Scientific Research (B) (no. 23350075) from the Japan Society for the Promotion of Science (JSPS).

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Authors and Affiliations

  1. Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8571, Japan

    Satomi Tasaki, Atsuya Momotake & Tatsuo Arai

  2. Faculty of Science, University of the Ryukyus, Nishihara, Okinawa, 903-0213, Japan

    Yoko Kanna

Authors
  1. Satomi Tasaki
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  2. Atsuya Momotake
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  3. Yoko Kanna
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  4. Tatsuo Arai
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Correspondence to Tatsuo Arai.

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Tasaki, S., Momotake, A., Kanna, Y. et al. Excited state intramolecular hydrogen atom transfer of phenylethynyl-substituted 2′-hydroxychalcones. Res Chem Intermed 39, 61–72 (2013). https://doi.org/10.1007/s11164-012-0632-8

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  • DOI: https://doi.org/10.1007/s11164-012-0632-8

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