Skip to main content
Log in

Photodimerization of hydrophobic guests within a water-soluble nanocapsule

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Conducting reactions in environmentally benign conditions is one of the major objectives of “green chemistry.” In this context, developing ways to conduct reactions in water seems obvious. In this report, we present our results on photodimerization of select guest molecules placed within the rigid reaction cavity of a water-soluble cavitand, octa acid. The results presented herein highlight the value of a supramolecular approach in achieving selectivity in photoreactions and opening reaction pathways that are latent in solution chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5
Scheme 3
Fig. 6
Fig. 7
Scheme 4
Fig. 8
Fig. 9
Scheme 5

Similar content being viewed by others

References

  1. N.J. Turro, V. Ramamurthy, J.C. Scaiano, Modern Molecular Photochemistry of Organic Molecules (University Science Books, Sausalito, 2010)

    Google Scholar 

  2. R.G. Weiss, V. Ramamurthy, G.S. Hammond, Acc. Chem. Res. 26, 530 (1993)

    Article  CAS  Google Scholar 

  3. V. Ramamurthy, Photochemistry in Organized & Constrained Media (VCH, New York, 1991)

    Google Scholar 

  4. V. Ramamurthy, R.G. Weiss, G.S. Hammond, in Advances in Photochemistry, ed. by D.H. Volman, G.S. Hammond, D.C. Neckers (Wiley, New York, 1993)

  5. M.D. Cohen, Angew. Chem. Int. Ed. Engl. 14, 386 (1975)

    Article  Google Scholar 

  6. G.M.J. Schmidt, Pure Appl. Chem. 27, 647 (1971)

    Article  CAS  Google Scholar 

  7. G.R. Desiraju, Crystal Engineering: The Design of Organic Solids (Elsevier, Amsterdam, 1989)

    Google Scholar 

  8. P. De Mayo, L.K. Sydnes, J. Chem. Soc. Chem. Commun. 994 (1980)

  9. K. Gnanaguru, G.S. Murthy, K. Venkatesan, V. Ramamurthy, Chem. Phys. Lett. 109, 255 (1984)

    Article  CAS  Google Scholar 

  10. K. Muthuramu, V. Ramamurthy, J. Org. Chem. 47, 3976 (1982)

    Article  CAS  Google Scholar 

  11. K. Muthuramu, N. Ramnath, V. Ramamurthy, J. Org. Chem. 48, 1872 (1983)

    Article  CAS  Google Scholar 

  12. V. Ramesh, V. Ramamurthy, J. Org. Chem. 49, 536 (1984)

    Article  CAS  Google Scholar 

  13. Y. Tao, H. Kanoh, L. Abrams, K. Kaneko, Chem. Rev. 106, 896 (2006)

    Article  CAS  Google Scholar 

  14. B.R. Bhogala, B. Captain, A. Parthasararthy, V. Ramamurthy, J. Am. Chem. Soc. 132, 13434 (2010)

    Article  CAS  Google Scholar 

  15. M. Pattabiraman, L.S. Kaanumalle, A. Natarajan, V. Ramamurthy, Langmuir 22, 7605 (2006)

    Article  CAS  Google Scholar 

  16. R. Kaliappan, M.V.S.N. Maddipatla, L.S. Kaanumalle, V. Ramamurthy, Photochem. Photobiol. Sci. 6, 737 (2007)

    Article  CAS  Google Scholar 

  17. M.V.S.N. Maddipatla, L.S. Kaanumalle, A. Natarajan, M. Pattabiraman, V. Ramamurthy, Langmuir 23, 7545 (2007)

    Article  CAS  Google Scholar 

  18. B. Mondal, B. Captain, V. Ramamurthy, Photochem. Photobiol. Sci. 10, 891 (2011)

    Article  CAS  Google Scholar 

  19. S. Karthikeyan, V. Ramamurthy, J. Org. Chem. 71, 6409 (2006)

    Article  CAS  Google Scholar 

  20. L.S. Kaanumalle, V. Ramamurthy, Chem. Commun. 1062 (2007)

  21. R. Breslow, Artificial Enzymes (Wiley, Weinheim, 2005)

    Book  Google Scholar 

  22. R. Breslow, S.D. Dong, Chem. Rev. 98, 1997 (1998)

    Article  CAS  Google Scholar 

  23. V.T. D’Souza, M.L. Bender, Acc. Chem. Res. 20, 146 (1987)

    Article  Google Scholar 

  24. D.J. Cram, J.M. Cram, Container Molecules and Their Guests (Royal Society of Chemistry, Cambridge, 1997)

    Google Scholar 

  25. W. Sliwa, C. Kozlowski, Calixarenes and Resorcinarenes (Wiley-VCH Verlag, Weinheim, 2009)

    Google Scholar 

  26. C.L.D. Gibb, B.C. Gibb, J. Am. Chem. Soc. 126, 11408 (2004)

    Article  CAS  Google Scholar 

  27. N. Jayaraj, Y. Zhao, A. Parthasarathy, M. Porel, R.S.H. Liu, V. Ramamurthy, Langmuir 25, 10575 (2009)

    Article  CAS  Google Scholar 

  28. L.S. Kaanumalle, C.L.D. Gibb, B.C. Gibb, V. Ramamurthy, J. Am. Chem. Soc. 127, 3674 (2005)

    Article  CAS  Google Scholar 

  29. M. Porel, N. Jayaraj, L.S. Kaanumalle, M.V.S.N. Maddipatla, A. Parthasarathy, V. Ramamurthy, Langmuir 25, 3473 (2009)

    Article  CAS  Google Scholar 

  30. B.H. Clampitt, J.W. Callis, J. Phys. Chem. 66, 201 (1962)

    Article  CAS  Google Scholar 

  31. F.D. Lewis, S.L. Quillen, P.D. Hale, J.D. Oxman, J. Am. Chem. Soc. 110, 1261 (1988)

    Article  CAS  Google Scholar 

  32. S. Karthikeyan, V. Ramamurthy, J. Org. Chem. 72, 452 (2007)

    Article  CAS  Google Scholar 

  33. F.D. Lewis, J.E. Elbert, A.L. Upthagrove, P.D. Hale, J. Am. Chem. Soc. 110, 5191 (1988)

    Article  CAS  Google Scholar 

  34. F.D. Lewis, M. Kojima, J. Am. Chem. Soc. 110, 8660 (1988)

    Article  CAS  Google Scholar 

  35. F.D. Lewis, J.D. Oxman, L.L. Gibson, H.L. Hampsch, S.L. Quillen, J. Am. Chem. Soc. 108, 3005 (1986)

    Article  CAS  Google Scholar 

  36. M. Porel, N. Jayaraj, S. Raghothama, V. Ramamurthy, Org. Lett. 12, 4544 (2010)

    Article  CAS  Google Scholar 

  37. T. Asanuma, M. Yamamoto, Y. Nishijima, J. Chem. Soc. Chem. Commun., 608 (1975)

  38. H. Nozaki, I. Otani, R. Noyori, M. Kawanisi, Tetrahedron 24, 2183 (1968)

    Article  CAS  Google Scholar 

  39. T. Asanuma, T. Gotoh, A. Tsuchida, M. Yamamoto, Y. Nishijima, J. Chem. Soc. Chem. Commun., 485 (1977)

  40. M. Kojima, H. Sakuragi, K. Tokumaru, Bull. Chem. Soc. Jpn. 62, 3863 (1989)

    Article  CAS  Google Scholar 

  41. L. Brancaleon, D. Brousmiche, V.J. Rao, L.J. Johnston, V. Ramamurthy, J. Am. Chem. Soc. 120, 4926 (1998)

    Article  CAS  Google Scholar 

  42. M. Yasuda, C. Pac, H. Sakurai, Bull. Chem. Soc. Jpn. 53, 502 (1980)

    Article  CAS  Google Scholar 

  43. W. Metzner, D. Wendisch, Justus Liebigs Ann. Chem. 730, 111 (1969)

    CAS  Google Scholar 

  44. C. DeBoer, J. Am. Chem. Soc. 91, 1855 (1969)

    Article  CAS  Google Scholar 

  45. T. Majima, C. Pac, A. Nakasone, H. Sakurai, J. Am. Chem. Soc. 103, 4499 (1981)

    Article  CAS  Google Scholar 

  46. P.E. Eaton, J. Am. Chem. Soc. 84, 2344 (1962)

    Article  CAS  Google Scholar 

  47. J.L. Ruhlen, P.A. Leermakers, J. Am. Chem. Soc. 89, 4944 (1967)

    Article  CAS  Google Scholar 

  48. E.Y.Y. Lam, D. Valentine, G.S. Hammond, J. Am. Chem. Soc. 89, 3482 (1967)

    Article  CAS  Google Scholar 

  49. G. Lem, N.A. Kaprinidis, D.I. Schuster, N.D. Ghatlia, N.J. Turro, J. Am. Chem. Soc. 115, 7009 (1993)

    Article  CAS  Google Scholar 

  50. J. Yang, M.B. Dewal, S. Profeta Jr, M.D. Smith, Y. Li, L.S. Shimizu, J. Am. Chem. Soc. 130, 612 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

V.R. is grateful to the National Science Foundation, USA for generous financial support (CHE-0848017). V.R. fondly recalls the visit to Professor Mizuno’s laboratory at Osaka and meeting him at various conferences around the world. V.R. wishes Professor Katsuhiko Mizuno a fulfilling and healthy life after decades of intense scientific career at Osaka Prefecture University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. Ramamurthy.

Additional information

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2195 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Parthasarathy, A., Samanta, S.R. & Ramamurthy, V. Photodimerization of hydrophobic guests within a water-soluble nanocapsule. Res Chem Intermed 39, 73–87 (2013). https://doi.org/10.1007/s11164-012-0633-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0633-7

Keywords

Navigation