Skip to main content
SpringerLink
Log in

Photocontrol of Ion Extraction and Ion Transport by Photofunctional Crown Ethers

  • Chapter
Host Guest Complex Chemistry / Macrocycles

Abstract

Photoresponsive systems are ubiquitously seen in nature: photosynthesis, vision, phototropism, and phototaxis are typical examples. In these systems, light is used as a trigger to cause subsequent life processes. We have been interested in the application of the phenomena to biomimetic systems. To imitate the fundamental functions of such photoresponsive systems, one has to combine within a molecule a photoantenna to capture a photon with a functional group to mediate a subsequent event. Host molecules have drawn attention as simplified enzyme model systems. We assumed that the photocontrol of host molecules, as well as that of enzymes 1–3) might provide a somewhat new field of chemistry.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bieth, J. et al.: Proc. Natl. Acad. Sci. U.S.A. 66, 850 (1970)

    Article  CAS  Google Scholar 

  2. Berezin, I. V. et al.: FEBS Lett. 30, 329 (1974)

    Article  Google Scholar 

  3. Karuhe. T.. Nakamoto. Y.. Suzuki, S.: Biochim. Biophys. Acta 445, 774 (1976)

    Google Scholar 

  4. Shinkai, S., Ogawa, T., Nakaji, T., Kusano, Y., Manabe, O.: Tetrahedron Lett. 1979, 4569

    Google Scholar 

  5. Shinkai, S. et al.: J. Am. Chem. Soc. 102, 5860 (1980)

    Article  CAS  Google Scholar 

  6. Ammon, L., Shinkai, S.: to be submitted

    Google Scholar 

  7. Fisher, D. P. et al.: J. Am. Chem. Soc. 99, 2811 (1977)

    Article  CAS  Google Scholar 

  8. Nakamura, A., Aotake, M., Otsuka, S.: ibid. 96, 3456 (1974)

    CAS  Google Scholar 

  9. Shinkai, S., Minami, T., Kouno, T., Kusano, Y., Manabe, O.: Chem. Lett. 1982, 499

    Google Scholar 

  10. Shinkai, S. et al.: J. Chem. Soc. Perkin 2 1982, 2741

    Google Scholar 

  11. Shinkai, S., Shigematsu, K., Honda, Y. Manabe, O.: to be submitted

    Google Scholar 

  12. Wildes, P. D., Pacifici, J. G., Irick, G., Whitten, D. G.: J. Am. Chem. Soc. 93, 2004 (1971)

    Google Scholar 

  13. Harberfield, P. et al.: J. Am. Chem. Soc. 97, 5804 (1975)

    Article  Google Scholar 

  14. a) Asano, T.: J. Am. Chem. Soc. 102, 1205 (1980)

    Article  CAS  Google Scholar 

  15. Asano, T. et al.: ibid. 104, 4900 (1982)

    CAS  Google Scholar 

  16. Nishimura, N. et al.: Bull. Chem. Soc. Jpn. 49, 1381 (1976)

    Article  CAS  Google Scholar 

  17. Schanze, K. S., Mattox, T. F., Whitten, D. G.: J. Am. Chem. Soc. 104, 1733 (1982)

    Article  CAS  Google Scholar 

  18. Shinkai, S. et al.: Chem. Lett. 1980, 1303

    Google Scholar 

  19. Asano, T. et al.: J. Am. Chem. Soc. 103, 5161 (1981)

    Article  CAS  Google Scholar 

  20. Rau, H., Lüddecke, E.: ibid. 104, 1616 (1982)

    CAS  Google Scholar 

  21. a) Ueno, A. et al.: ibid. 101, 2779 (1979)

    Google Scholar 

  22. Ueno, A. et al.: Chem. Lett. 1979, 841

    Google Scholar 

  23. Emert, J., Breslow, R.: J. Am. Chem. Soc. 97, 670 (1975)

    Article  CAS  Google Scholar 

  24. Ueno, A. et al.: Chem. Lett. 1979, 1007

    Google Scholar 

  25. Ueno, A. et al.: J. Chem. Soc. Chem. Commun. 1981, 94

    Google Scholar 

  26. Irie, M., Hayashi, K.: J. Macromol. Sci.-Chem. A13, 511 (1979)

    Article  Google Scholar 

  27. Irie, M. et al.: Macromolecules 14, 262 (1981)

    Article  CAS  Google Scholar 

  28. Blair, H. S., et al.: Polymer 21, 1195 (1980)

    Article  CAS  Google Scholar 

  29. Irie, M. et al.: J. Polym. Sci. Polym. Lett. Ed. 17, 29 (1979)

    Google Scholar 

  30. Negishi, N..et al.: Kobunshi Ronbun Shu 37, 293 (1980)

    Article  CAS  Google Scholar 

  31. Blasius, E., Maurer, P.-G.: Makromol. Chem. 178, 649 (1977)

    Article  CAS  Google Scholar 

  32. Bormann, S. et al.: Tetrahedron 31, 2791 (1975)

    Article  CAS  Google Scholar 

  33. Smid, J. et al.: J. Am. Chem. Soc. 97, 5932 (1975)

    Article  CAS  Google Scholar 

  34. Wong, L., Smid, J.: ibid. 99, 5637 (1977)

    CAS  Google Scholar 

  35. Shinkai, S., Kinda, H., Manabe, O.: ibid. 104, 2933 (1982)

    CAS  Google Scholar 

  36. Shinkai, S. et al.: unpublished result

    Google Scholar 

  37. Shinkai, S., Honda, Y., Kusano, Y., Manabe, O.: J. Chem. Soc. Chem. Commun. 1982, 848

    Google Scholar 

  38. Shinkai, S. et al.: Bull. Chem. Soc. Jpn. 56, 1700 (1983)

    Article  CAS  Google Scholar 

  39. Shinkai, S., Ueda, K., Honda, Y., Manabe, O.: to be submitted

    Google Scholar 

  40. a) Desvergne, J.-P., Bouas-Laurent, H.: J. Chem. Soc. Chem. Commun. 1978, 403

    Google Scholar 

  41. Bouas-Laurent, H. et al.: Pure and Appl. Chem. 52, 2633 (1980)

    Article  CAS  Google Scholar 

  42. Yamashita, I. et al.: Tetrahedron Lett. 1980, 541

    Google Scholar 

  43. Eichner, M., Merz, A.: ibid. 22, 1315 (1981)

    CAS  Google Scholar 

  44. Shiga, M., Takagi, M., Ueno, K.: Chem. Lett. 1980, 1021

    Google Scholar 

  45. Shinkai, S., Minami, T., Kusano, Y., Manabe, O.: Tetrahedron Lett. 23, 2581 (1982)

    Article  CAS  Google Scholar 

  46. Shinkai, S. et al.: J. Am. Chem. Soc. 105, 1851 (1983)

    Article  CAS  Google Scholar 

  47. Kimura, K. et al.: Chem. Lett. 1979, 611

    Google Scholar 

  48. Maeda, T., Kimura, K., Shono, T.: Bull. Chem. Soc. Japan 55, 3506 (1982)

    Article  CAS  Google Scholar 

  49. Mollison, P. R., Turter, M. R.: J. Chem. Soc. Perkin 2 1982, 1818

    Google Scholar 

  50. Shinkai, S. et al.: J. Chem. Soc. Perkin 1 1981, 3279

    Article  Google Scholar 

  51. Shinkai, S., Ogawa, T., Kusano, Y., Manabe, O.: Chem. Lett. 1980, 283

    Google Scholar 

  52. Shinkai, S. et al.: J. Am. Chem. Soc. 103, 111 (1981)

    Article  CAS  Google Scholar 

  53. Shinkai, S. et al.: J. Am. Chem. Soc. 104, 1960 (1982)

    Article  CAS  Google Scholar 

  54. Blank, M. et al.: Science 214, 70 (1981)

    Article  CAS  Google Scholar 

  55. Choy, E. M. et al.: J. Am. Chem. Soc. 96, 7085 (1974)

    Article  CAS  Google Scholar 

  56. Cussler, E. L.: Am. Inst. Chem. Eng. J. 17, 1300 (1971)

    CAS  Google Scholar 

  57. Wierenga, W. et al.: J. Am. Chem. Soc. 101, 1334 (1979)

    Article  CAS  Google Scholar 

  58. Frederick, L. A. et al.: J. Chem. Soc. Chem. Commun. 1980, 1211

    Google Scholar 

  59. Shinkai, S. et al.: Tetrahedron Lett. 21, 4463 (1980)

    Article  CAS  Google Scholar 

  60. Shinkai, S., Minami, T., Kusano, Y., Manabe, O.: J. Am. Chem. Soc. 104, 1967 (1982)

    Article  CAS  Google Scholar 

  61. Yamazaki, N. et al.: Tetrahedron Lett. 1978, 2429

    Google Scholar 

  62. Kubokawa, H. et al.: Chem. Lett. 1982, 1937

    Google Scholar 

  63. Yamazaki, N. et al.: J. Macromol. Sci.-Chem. A13, 321 (1079)

    Google Scholar 

  64. Gardner, J. O., Beard, C. C.: J. Med. Chem. 21, 357 (1978)

    Article  CAS  Google Scholar 

  65. Hiratani, K. et al.: Chem. Lett. 1980, 477

    Google Scholar 

  66. Hiratani, K.: ibid. 1981, 21

    Google Scholar 

  67. Rebek, J., Jr. et al.: J. Am. Chem. Soc. 101, 4333 (1979)

    Article  CAS  Google Scholar 

  68. Van Bergen, T. J., Kellogg, R. M.: ibid. 99, 3882 (1977)

    Google Scholar 

  69. De Vries, J. G., Kellogg, R. M.: ibid. 101, 2759 (1979)

    Google Scholar 

  70. Behr, J.-P., Lehn, J.-M.: J. Chem. Commun. 1978, 143

    Google Scholar 

  71. Shinkai, S. et al.: Tetrahedron Lett. 24, 1539 (1983)

    Article  CAS  Google Scholar 

  72. Thanabal, V., Krishnan, V.: J. Am. Chem. Soc. 104, 3643 (1982)

    Article  CAS  Google Scholar 

  73. Chao, Y., Cram, D. J.: ibid. 98, 1015 (1976)

    CAS  Google Scholar 

  74. Matsui, T., Koga, K.: Tetrahedron Lett. 1978, 1115

    Google Scholar 

  75. Lehn, J.-M., Sirlin, C.: J. Chem. Soc. Chem. Commun 1978, 949

    Google Scholar 

  76. Minami, T., Shinkai, S., Manabe, O.: Tetrahedron Lett. 1982, 5167

    Google Scholar 

  77. Shinkai, S. et al.: Chem. Lett. 1983, 747 and unpublished results

    Google Scholar 

  78. Warshawsky, A., Kahana, N.: J. Am. Chem. Soc. 104, 2663 (1982)

    Article  CAS  Google Scholar 

  79. Brown, H. S. et al.: J. Org. Chem. 45, 1682 (1980)

    Article  CAS  Google Scholar 

  80. Schroder, G., Witt, W.: Angew. Chem. Int. Ed. Engl. 18, 311 (1979)

    Google Scholar 

  81. Pressman, B. C.: Ann. Rev. Biochem. 45, 501 (1976)

    Article  CAS  Google Scholar 

  82. Westly, J. W.: Ann. Rep. Med. Chem. 10, 246 (1975)

    Article  Google Scholar 

  83. Kobuke, Y. et al.: J. Am. Chem. Soc. 98, 7414 (1976)

    Article  CAS  Google Scholar 

  84. Kirch, M., Lehn, J.-M.: Angew. Chem. Int. Ed. Engl. 14, 555 (1975)

    Google Scholar 

  85. Lamb, J. D. et al.: J. Am. Chem. Soc. 102, 6820 (1980)

    Article  CAS  Google Scholar 

  86. Shinkai, S. et al.: J. Chem. Soc. Chem. Commun. 1980, 375

    Google Scholar 

  87. Shinkai, S., Shigematsu, K., Sato, M., Manabe, O.: J. Chem. Soc. Perkin 1 1982, 2735

    Google Scholar 

  88. Kumano, A. et al.: Chem. Lett. 1983, 1327

    Google Scholar 

  89. Ebrey, T. G., Honig, B.: Quat. Rev. Biophys. 8, 129 (1975)

    Article  CAS  Google Scholar 

  90. Montal, M.: Biochim. Biophys. Acta 559, 231 (1979)

    CAS  Google Scholar 

  91. Kaupp, U. B. et al.: ibid. 552, 390 (1979)

    CAS  Google Scholar 

  92. O’Brien, D. F.: Photochem. Photobiol. 29, 679 (1979)

    Article  Google Scholar 

  93. Tyminski, P. N. et al.: Biochemistry 21, 1197 (1982)

    Article  CAS  Google Scholar 

  94. Kano, K. et al.: Chem. Lett. 1980, 421

    Google Scholar 

  95. Kano, K. et al.: Photochem. Photobiol. 34, 322 (1981)

    Google Scholar 

  96. Ring, K.: Angew. Chem. Int. Ed. Eng1.9,345(1970)

    Google Scholar 

  97. Behr,J.-P.,Lehn,J.-M.:J.Am.Chem.Soc.95,6108(1973)

    Google Scholar 

  98. Newcomb,M.etal.:ibid.101,4941(1979)

    Google Scholar 

  99. Maruyama, K. et al.: Tetrahedron Lett. 22, 2001 (1981)

    Article  CAS  Google Scholar 

  100. Tsukube, H.: ibid. 22, 3981 (1981)

    CAS  Google Scholar 

  101. Sunamoto, J. et al.: J. Am. Chem. Soc. 104, 5502 (1982)

    Article  CAS  Google Scholar 

  102. Rebek, J., Jr., Wattley, R.: ibid. 102, 4853 (1980)

    CAS  Google Scholar 

  103. Shinbo, T. et al.: Nature 270, 277 (1977)

    Article  CAS  Google Scholar 

  104. Shinbo, T. et al.: Chem. Lett. 1979, 1177

    Google Scholar 

  105. Grimaldi, J. J., Lehn, J.-M.: J. Am. Chem. Soc. 101, 1333 (1979)

    Article  CAS  Google Scholar 

  106. Matsuo, S. et al.: Chem. Lett. 1981, 1543

    Google Scholar 

  107. Burgmayer, P., Murray, R. W.: J. Am. Chem. Soc. 104, 6139 (1982)

    Article  CAS  Google Scholar 

  108. Shimidzu, T. et al.: Makromol. Chem. 178, 1923 (1977)

    Article  CAS  Google Scholar 

  109. Shimidzu, T. et al.: Macromolecules 14, 170 (1981)

    Article  CAS  Google Scholar 

  110. Shimidzu, T. et al.: Polym. J. 12, 363 (1980)

    Article  CAS  Google Scholar 

  111. Ogata, N. et al.: J. Polym. Lett. Ed. 25, 1419 (1980)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University, Nagasaki 852, Japan

    Seiji Shinkai & Osamu Manabe

Authors
  1. Seiji Shinkai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Osamu Manabe
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Straße 1, 5300, Bonn 1, Germany

    Fritz Vögtle  & Edwin Weber  & 

Rights and permissions

Reprints and permissions

Copyright information

© 1985 Springer-Verlag, Berlin, Heidelberg

About this chapter

Cite this chapter

Shinkai, S., Manabe, O. (1985). Photocontrol of Ion Extraction and Ion Transport by Photofunctional Crown Ethers. In: Vögtle, F., Weber, E. (eds) Host Guest Complex Chemistry / Macrocycles. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-70108-5_6

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-70108-5_6

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-13950-8

  • Online ISBN: 978-3-642-70108-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation