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Metal-Induced Structural Switching of a Folded Quinone-Sandwiched Porphyrin

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Abstract

We report the synthesis of a novel quinone-sandwiched porphyrin in which two benzoquinones are connected oppositely at the meso positions of a porphyrin through rigid 3-amido 2,2′-bipyridine linkers. 1H-NMR and single crystal X-ray analyses revealed that the quinone-sandwiched porphyrin has a folded structure in which the porphyrin unit was inserted into the two quinone moieties via π-stacking. Insertion of a Zn(II) ion into the porphyrin center induced a drastic conformational change which is resulted in coordination of the oxygen atoms of both benzoquinone moieties to the Zn-porphyrin to afford a 6-coordinated structure.

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References

  1. V. Balzani, P. Piotrowiak, M.A.J. Rodgers, J. Mattay, D. Astruc, H.B. Gray, S. Fukuzumi, T.E. Mallouk, Y. Haas, A.P. de Silva, I.R. Gould (eds.), Electron Transfer in Chemistry I–V (Wiley-VCH, Weinheim, 2001)

    Google Scholar 

  2. M.A. Wasielewski, Acc. Chem. Res. 42, 1910 (2009)

    Article  CAS  Google Scholar 

  3. K. M. Kadish, K. M. Smith, R. Guiard (eds.), The Porphyrin Handbook, vols. 1–20 (Academic Press, New York, 2000/2003)

  4. H. Imahori, T. Umeyama, K. Kurotobi, Y. Takano, Chem. Commun. 48, 4032 (2012)

    Article  CAS  Google Scholar 

  5. J.K. Delaney, D.C. Mauzerall, J.S. Linsey, J. Am. Chem. Soc. 100, 957 (1990)

    Article  Google Scholar 

  6. H. Tsue, H. Imahori, T. Kaneda, Y. Tanaka, T. Okada, K. Tamaki, Y. Sakata, J. Am. Chem. Soc. 122, 2279 (2000)

    Article  CAS  Google Scholar 

  7. H.A. Staab, B. Krauzer, S. Quazzotti, Eur. J. Org. Chem. 1998, 2149 (1998)

    Article  Google Scholar 

  8. T. Häberle, J. Hirsch, F. Pöllinger, H. Heitele, M.E. Michel-Beyerle, C. Anders, A. Döhling, C. Krieger, A. Rückemann, H.A. Staab, J. Phys. Chem. 100, 18269 (1996)

    Article  Google Scholar 

  9. H.A. Staab, C. Krieger, C. Anders, A. Rückemann, Chem. Ber. 127, 231 (1994)

    Article  CAS  Google Scholar 

  10. H.A. Staab, A. Feurer, R. Hauck, Angew. Chem. Int. Ed. Engl. 33, 2428 (1994)

    Article  Google Scholar 

  11. M. Kanematsu, P. Naumov, T. Kojima, S. Fukuzumi, Chem. Eur. J. 17, 12372 (2011)

    Article  CAS  Google Scholar 

  12. Y.K. Kang, P.M. Iovine, M.J. Therien, Coord. Chem. Rev. 255, 804 (2011)

    Article  CAS  Google Scholar 

  13. Y.K. Kang, I.V. Rubtsov, P.M. Iovine, J. Chen, M.J. Therien, J. Am. Chem. Soc. 124, 8275 (2002)

    Article  CAS  Google Scholar 

  14. C.-H. Lee, J.S. Linsey, Tetrahedron 50, 11427 (1994)

    Article  CAS  Google Scholar 

  15. M. Eipert, C. Maichle-Mössemer, M.E. Maier, J. Org. Chem. 67, 8692 (2002)

    Article  CAS  Google Scholar 

  16. G.M. Sheldrick, SHELX-97, Program for the Refinement of Crystal Structures (University of Gottingen, Gottingen, 1997)

    Google Scholar 

  17. D.T. Gryko, M. Tasior, Tetrahedron Lett. 44, 3317 (2003)

    Article  CAS  Google Scholar 

  18. M. Linke-Schaetzel, C.E. Anson, A.K. Powell, G. Buth, E. Palomares, J.D. Durrant, T.S. Balaban, J.-M. Lehn, Chem. Eur. J. 12, 1931 (2006)

    Article  CAS  Google Scholar 

  19. A.W. Kleji, M. Kuil, D.M. Tooke, A.L. Spek, J.N.H. Reek, Inorg. Chem. 44, 7696 (2005)

    Article  Google Scholar 

  20. R.S. Kishore, T. Paululat, M. Schmittel, Chem. Eur. J. 12, 8136 (2006)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by Grant-in-Aids for Scientific Research on Innovative Areas “Coordination Programming” (area 2107, No. 21108012) to K.T. and the Global COE Program for “Elucidation and Design of Materials and Molecular Functions” to K.T. from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

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Correspondence to Kentaro Tanaka.

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This paper is dedicated to Prof. Dr. Hiroshi Nishihara for his outstanding contribution to the field of metal-containing polymers.

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Yamada, Y., Tanaka, K. Metal-Induced Structural Switching of a Folded Quinone-Sandwiched Porphyrin. J Inorg Organomet Polym 23, 180–185 (2013). https://doi.org/10.1007/s10904-012-9726-4

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  • DOI: https://doi.org/10.1007/s10904-012-9726-4

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