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[5]Rotaxane and [5]Pseudorotaxane Based on Cucurbit[6]uril and Anchored to a Meso-tetraphenyl Porphyrin

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Abstract

Water soluble [5]rotaxane and [5]pseudorotaxane based on cucurbit[6]uril and anchored to a meso-tetraphenyl porphyrin have been synthesized and characterized by spectroscopic methods (1H-NMR, 13C-NMR and UV), and by elemental analysis, and mass spectrometry. The preliminary results of the pH-driven switching properties of [5]rotaxane investigated through 1H-NMR spectroscopy are reported. These results were compared with those obtained from a model porphyrin, which was prepared by the de-threading cucurbit[6]uril from [5]pseudorotaxane under basic conditions.

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References

  1. (a) On molecular machine and motors: Special issue of Account of Chemical Research, 2001, 6, guest-edited by Stoddart, J.F; (b) J.W. Steed and J.L. Atwood: Supramolecular Chemistry, John Wiley and Sons, Ltd, (2000)

  2. (a) S.A. Nepogodiev and J.F. Stoddart: Chem. Rev. 98, 1959 (1998); (b) Molecular Catenanes, Rotaxanes, and Knots, ed. J.-P. Sauvage, C.O. Dietrich-Buchecker, Wiely-VCH, Weinheim (1999)

  3. Badjic J.D., Balzani V., Credi A., Silvi S., Stoddart J.F., 2004 Science 303: 1847

    Article  Google Scholar 

  4. (a) W.L. Mock: In F. Vogtle (ed.), Comprehensive Supramolecular Chemistry, Vol. 2, Pergamon, Oxford (1996), 477; (b) K. Kim: Chem. Soc. Rev. 31, 96 (2002); (c) J. Lagona, P. Mukhopadhyay, S. Chakrabarti, and L. Isaacs: Angew. Chem. Int. Ed. 44, 4844 (2005)

  5. Tuncel D., Steinke J.H.G., 2004 Macromolecules 37: 288

    Article  CAS  Google Scholar 

  6. (a) J.W. Lee, K. Kim, and K. Kim: Chem. Commun. 1042 (2001); (b) S.I. Jun, J.W. Lee, S. Sakamoto, K. Yamaguchi, and K. Kim: Tetrahedron Lett. 41, 471 (2000)

  7. (a) M.-S. Choi, T. Yamazaki, I. Yamazaki, and T. Aida: Angew. Chem. Int. Ed. 43, 150 (2004); (b) A.K. Burrell, D.L. Officer, P.G. Plieger, and D.C. Reid: Chem. Rev. 101, 2751 (2001)

  8. (a) L.M. Scolaro, A. Romeo, and R.F. Pasternack: J. Am. Chem. Soc. 126, 7178 (2004); (b) C.N. Lunardi and A.C. Tedesco: Curr. Org. Chem. 9, 813 (2005)

  9. (a) G. Moschetto, R. Lauceri, F.G. Gulino, D. Sciotto, and R.␣Purrello: J. Am. Chem. Soc. 124, 14536 (2002); (b) R.G.E. Coumans, J.A.A.W. Elemans, P. Thordarson, R.J.M. Nolte, and E. Rowan: Angew. Chem. Int. Ed. 42, 650 (2003); (c) K. Kano, R.␣Nishiyabu, T. Yamazaki, and I. Yamazaki: J. Am. Chem. Soc. 125, 10625 (2003); (d) D. Kuciauskas, P.A. Liddell, S. Lin, T.E. Johnson, S.J. Weghorn, J.S. Lindsey, A.L. Moore, and D. Gust: J.␣Am. Chem. Soc. 121, 8604 (1999); (e) D.L. Dick, T.V.S. Rao, D. Sukumaran, and D.S. Lawrence: J. Am. Chem. Soc. 114, 2664 (1992); (f) K. Kano, R. Nishiyabu, T. Asada, and Y. Kuroda: J.␣Am. Chem. Soc. 124, 9937 (2002); (g) K. Kano, R. Nishiyabu, and R. Doi: J. Org. Chem. 70, 3667 (2005)

  10. Wen L., Li M., Schlenoff J.B., 1997 J. Am. Chem. Soc. 119: 7726

    Article  CAS  Google Scholar 

  11. (a) W.L. Mock and N.-Y. Shih: J. Org. Chem. 51, 4440 (1986); (b) W.L. Mock and N.-Y. Shih: J. Am. Chem. Soc. 110, 4706 (1988); (c) W.A. Freeman: Acta Crystallgr., Sect. B B40, 382 (1984)

  12. At pH < 4, UV–Vis spectrum reveals one absorption peak due to Soret Band at 432 nm and two absorption bands due to Q band at 593 and 647 nm, whereas at pH > 4 the Soret Band appears at 414 nm along with four bands for the Q band at 515, 553, 588 and 637 nm

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Acknowledgements

This research was supported by the Scientific and Technical Research Council of Turkey (TUBITAK, Grant No: MISAG 260) and by a Bilkent University Faculty Development Grant. The authors thank the Chemistry Department of Hacettepe University and the TUBITAK Analysis Centre for the NMR, and Dr. M. Katterle (Potsdam University) and Prof. B. Salih (Chemistry Department of Hacettepe University) for MALDI-TOF measurements.

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  1. Chemistry Department, Bilkent University, 06800, Ankara, Turkey

    Dönüs Tuncel, Nesibe Cindir & Ünsal Koldemir

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  1. Dönüs Tuncel
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  2. Nesibe Cindir
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  3. Ünsal Koldemir
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Correspondence to Dönüs Tuncel.

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Tuncel, D., Cindir, N. & Koldemir, Ü. [5]Rotaxane and [5]Pseudorotaxane Based on Cucurbit[6]uril and Anchored to a Meso-tetraphenyl Porphyrin. J Incl Phenom Macrocycl Chem 55, 373–380 (2006). https://doi.org/10.1007/s10847-006-9112-3

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  • DOI: https://doi.org/10.1007/s10847-006-9112-3

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