Skip to main content

Thiacalixarenes

  • Chapter
  • First Online:
Calixarenes and Beyond

Abstract

This review focuses on the emergence of supramolecular functions arising from the synergy between thiacalixarene and other components, particularly metal ions. The functions described in this review are separation, catalysis, cage formation, magnetism, luminescence, and sensing, which are not realized by covalent modification of the thiacalixarenes. Fundamental functions such as inclusion and complexation, as well as some new synthetic and modification methods of thiacalixarene, will be discussed prior to discussing the supramolecular functions. The examples also cover the cases of other sulfur-bridged entities: sulfinyl- and sulfonylcalixarenes. Emphasis is placed on the fact that the multifunctionality of the sulfur-bridged calixarene is the key to realize these supramolecular functions. This is almost the sole reason why thiacalixarene is valuable in chemistry.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 219.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 279.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 279.99
Price excludes VAT (USA)
  • Durable hardcover 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

References

  1. Sone, T.; Ohba, Y.; Moriya, K.; Kumada, H.; Ito, K. Tetrahedron 1997, 53, 10689–10698.

    Article  CAS  Google Scholar 

  2. Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Tetrahedron Lett. 1997, 38, 3971–3972.

    Article  CAS  Google Scholar 

  3. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.

    Google Scholar 

  4. Iki, N.; Miyano, S. J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 99–105.

    Article  CAS  Google Scholar 

  5. Morohashi, N.; Iki, N.; Miyano, S. Yuki Gosei Kagaku Kyokaishi 2002, 60, 550–562.

    Article  CAS  Google Scholar 

  6. Lhoták, P. Eur. J. Org. Chem. 2004, 1675–1692.

    Google Scholar 

  7. Morohashi, N.; Narumi, F.; Iki, N.; Hattori, T.; Miyano, S. Chem. Rev. 2006, 106, 5291–5316.

    Article  CAS  Google Scholar 

  8. Iki, N. J. Inclusion Phenom. Macrocyclic Chem. 2009, 64, 1–13.

    Article  CAS  Google Scholar 

  9. Iki, N. Supramol. Chem. 2011, 23, 160–168.

    Article  CAS  Google Scholar 

  10. Kumar, R.; Lee, Y. O.; Bhalla, V.; Kumar, M.; Kim, J. S. Chem. Soc. Rev. 2014, 43, 4824–4870.

    Article  CAS  Google Scholar 

  11. Iki, N.; Ogawa, S.; Matsue, T.; Miyano, S. J. Electroanal. Chem. 2007, 610, 90–95.

    Article  CAS  Google Scholar 

  12. Iki, N.; Morohashi, N.; Suzuki, T.; Ogawa, S.; Aono, M.; Kabuto, C.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyano, S. Tetrahedron Lett. 2000, 41, 2587–2590.

    Article  CAS  Google Scholar 

  13. Kondo, Y.; Ulzii, M.; Itoh, S.; Yamada, M.; Hamada, F. Int. J. Soc. Mater. Eng. Resour. 2014, 20, 103–108.

    Article  CAS  Google Scholar 

  14. Morohashi, N.; Iki, N.; Aono, M.; Miyano, S. Chem. Lett. 2002, 31, 494–495.

    Article  Google Scholar 

  15. Kajiwara, T.; Kon, N.; Yokozawa, S.; Ito, T.; Iki, N.; Miyano, S. J. Am. Chem. Soc. 2002, 124, 11274–11275.

    Article  CAS  Google Scholar 

  16. Kajiwara, T.; Shinagawa, R.; Ito, T.; Kon, N.; Iki, N.; Miyano, S. Bull. Chem. Soc. Jpn. 2003, 76, 2267–2275.

    Article  CAS  Google Scholar 

  17. Iki, N.; Kabuto, C.; Fukushima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437–1443.

    Article  CAS  Google Scholar 

  18. Patel, M. H.; Shrivastav, P. S. Chem. Commun. 2009, 586–588.

    Google Scholar 

  19. Kundrat, O.; Eigner, V.; Dvorakova, H.; Lhoták, P. Org. Lett. 2011, 13, 4032–4035.

    Article  CAS  Google Scholar 

  20. Kundrat, O.; Dvorakova, H.; Bohm, S.; Eigner, V.; Lhoták, P. J. Org. Chem. 2012, 77, 2272–2278.

    Article  CAS  Google Scholar 

  21. Kundrat, O.; Dvorakova, H.; Eigner, V.; Lhoták, P. J. Org. Chem. 2010, 75, 407–411.

    Article  CAS  Google Scholar 

  22. Kundrat, O.; Kroupa, J.; Bohm, S.; Budka, J.; Eigner, V.; Lhoták, P. J. Org. Chem. 2010, 75, 8372–8375.

    Article  CAS  Google Scholar 

  23. Kundrat, O.; Cisarova, I.; Bohm, S.; Pojarova, M.; Lhoták, P. J. Org. Chem. 2009, 74, 4592–4596.

    Article  CAS  Google Scholar 

  24. Akdas, H.; Bringel, L.; Graf, E.; Hosseini, M. W.; Mislin, G.; Pansanel, J.; De Cian, A.; Fischer, J. Tetrahedron Lett. 1998, 39, 2311–2314.

    Article  CAS  Google Scholar 

  25. Morohashi, N.; Noji, S.; Nakayama, H.; Kudo, Y.; Tanaka, S.; Kabuto, C.; Hattori, T. Org. Lett. 2011, 13, 3292–3295.

    Article  CAS  Google Scholar 

  26. Morohashi, N.; Miyoshi, I.; Tonosaki, A.; Ohsugi, K.; Kitamoto, Y.; Hattori, T. In The 13th Host-Guest Chemistry Symposium, Japan Sendai, 2015, B-16.

    Google Scholar 

  27. Ebata, K.; Morohashi, N.; Hattori, T. In The 13th Host-Guest Chemistry Symposium, Japan Sendai, 2015, 1P-12.

    Google Scholar 

  28. Iki, N.; Morohashi, N.; Narumi, F.; Miyano, S. Bull. Chem. Soc. Jpn. 1998, 71, 1597–1603.

    Article  CAS  Google Scholar 

  29. Morohashi, N.; Iki, N.; Sugawara, A.; Miyano, S. Tetrahedron 2001, 57, 5557–5563.

    Article  CAS  Google Scholar 

  30. Iki, N.; Morohashi, N.; Kabuto, C.; Miyano, S. Chem. Lett. 1999, 28, 219–220.

    Article  Google Scholar 

  31. Harrowfield, J.; Koutsantonis, G. In Calixarenes in the Nanoworld; Vicens, J., Harrowfield, J., Baklouti, L., Eds.; Springer: Netherlands, 2007, p 197–212.

    Chapter  Google Scholar 

  32. Kajiwara, T.; Iki, N.; Yamashita, M. Coord. Chem. Rev. 2007, 251, 1734–1746.

    Article  CAS  Google Scholar 

  33. Bilyk, A.; Hall, A. K.; Harrowfield, J. M.; Hosseini, M. W.; Skelton, B. W.; White, A. H. Inorg. Chem. 2001, 40, 672–686.

    Article  CAS  Google Scholar 

  34. Bilyk, A.; Dunlop, J. W.; Fuller, R. O.; Hall, A. K.; Harrowfield, J. M.; Hosseini, M. W.; Koutsantonis, G. A.; Murray, I. W.; Skelton, B. W.; Sobolev, A. N.; Stamps, R. L.; White, A. H. Eur. J. Inorg. Chem. 2010, 2127–2152.

    Google Scholar 

  35. Bilyk, A.; Dunlop, J. W.; Fuller, R. O.; Hall, A. K.; Harrowfield, J. M.; Hosseini, M. W.; Koutsantonis, G. A.; Murray, I. W.; Skelton, B. W.; Stamps, R. L.; White, A. H. Eur. J. Inorg. Chem. 2010, 2106–02126.

    Google Scholar 

  36. Matsumiya, H.; Iki, N.; Miyano, S.; Hiraide, M. Anal. Bioanal. Chem. 2004, 379, 867–871.

    Article  CAS  Google Scholar 

  37. Matsumiya, H.; Hiraide, M. Bull. Chem. Soc. Jpn. 2005, 78, 1939–1943.

    Article  CAS  Google Scholar 

  38. Matsumiya, H.; Yasuno, S.; Iki, N.; Miyano, S. J. Chromatogr. A 2005, 1090, 197–200.

    Article  CAS  Google Scholar 

  39. Kikuchi, T.; Goto, I.; Suzuki, K. J. Nucl. Sci. Technol. 2006, 43, 690–693.

    Article  CAS  Google Scholar 

  40. Kikuchi, T.; Suzuki, K. J. Alloys Compd. 2006, 408–412, 1287–1290.

    Article  Google Scholar 

  41. Morohashi, N.; Hattori, T.; Yokomakura, K.; Kabuto, C.; Miyano, S. Tetrahedron Lett. 2002, 43, 7769–7772.

    Article  CAS  Google Scholar 

  42. Morohashi, N.; Yokomakura, K.; Hattori, T.; Miyano, S. Tetrahedron Lett. 2006, 47, 1157–1161.

    Article  CAS  Google Scholar 

  43. Proto, A.; Giugliano, F.; Capacchione, C. Eur. Polym. J. 2009, 45, 2138–2141.

    Article  CAS  Google Scholar 

  44. Floriani, C.; Floriani-Moro, R. In Calixarenes 2001; Kluwer Academic Publishers: 2001, p 536–560.

    Google Scholar 

  45. Yilmaz, M. In Calixarenes and Beyond; Neri, P., Ed.; Springer: 2016.

    Google Scholar 

  46. Limberg, C. Eur. J. Inorg. Chem. 2007, 3303–3314.

    Google Scholar 

  47. Su, K.; Jiang, F.; Qian, J.; Gai, Y.; Wu, M.; Bawaked, S. M.; Mokhtar, M.; Al-Thabaiti, S. A.; Hong, M. Cryst. Growth Des. 2014, 14, 3116–3123.

    Article  CAS  Google Scholar 

  48. Su, K.; Jiang, F.; Qian, J.; Pang, J.; Al-Thabaiti, S. A.; Bawaked, S. M.; Mokhtar, M.; Chen, Q.; Hong, M. Cryst. Growth Des. 2014, 14, 5865–5870.

    Article  CAS  Google Scholar 

  49. Bi, Y.; Wang, X.-T.; Liao, W.; Wang, X.; Wang, X.; Zhang, H.; Gao, S. J. Am. Chem. Soc. 2009, 131, 11650–11651.

    Article  CAS  Google Scholar 

  50. Gehin, A.; Ferlay, S.; Harrowfield, J. M.; Fenske, D.; Kyritsakas, N.; Hosseini, M. W. Inorg. Chem. 2012, 51, 5481–5486.

    Article  CAS  Google Scholar 

  51. Bi, Y.; Du, S.; Liao, W. Chem. Commun. 2011, 47, 4724–4726.

    Article  CAS  Google Scholar 

  52. Bi, Y.; Du, S.; Liao, W. Coord. Chem. Rev. 2014, 276, 61–72.

    Article  CAS  Google Scholar 

  53. Bi, Y.; Xu, G.; Liao, W.; Du, S.; Wang, X.; Deng, R.; Zhang, H.; Gao, S. Chem. Commun. 2010, 46, 6362–6364.

    Article  CAS  Google Scholar 

  54. Xiong, K.; Jiang, F.; Gai, Y.; He, Z.; Yuan, D.; Chen, L.; Su, K.; Hong, M. Cryst. Growth Des. 2012, 12, 3335–3341.

    Article  CAS  Google Scholar 

  55. Bi, Y.; Wang, S.; Liu, M.; Du, S.; Liao, W. Chem. Commun. 2013, 49, 6785–6787.

    Article  CAS  Google Scholar 

  56. Du, S.; Yu, T.-Q.; Liao, W.; Hu, C. Dalton Trans. 2015, 44, 14394–14402.

    Article  CAS  Google Scholar 

  57. Dai, F.-R.; Wang, Z. J. Am. Chem. Soc. 2012, 134, 8002–8005.

    Article  CAS  Google Scholar 

  58. Dai, F.-R.; Becht, D. C.; Wang, Z. Chem. Commun. 2014, 50, 5385–5387.

    Article  CAS  Google Scholar 

  59. Dai, F.-R.; Sambasivam, U.; Hammerstrom, A. J.; Wang, Z. J. Am. Chem. Soc. 2014, 136, 7480–7491.

    Article  CAS  Google Scholar 

  60. Kajiwara, T.; Hasegawa, M.; Ishii, A.; Katagiri, K.; Baatar, M.; Takaishi, S.; Iki, N.; Yamashita, M. Eur J Inorg Chem 2008, 5565–5568.

    Google Scholar 

  61. Bi, Y.; Wang, X.-T.; Liao, W.; Wang, X.; Deng, R.; Zhang, H.; Gao, S. Inorg. Chem. 2009, 48, 11743–11747.

    Article  CAS  Google Scholar 

  62. Desroches, C.; Pilet, G.; Borshch, S. A.; Parola, S.; Luneau, D. Inorg. Chem. 2005, 44, 9112–9120.

    Article  CAS  Google Scholar 

  63. Desroches, C.; Pilet, G.; Szilagyi, P. A.; Molnar, G.; Borshch, S. A.; Bousseksou, A.; Parola, S.; Luneau, D. Eur. J. Inorg. Chem. 2006, 357–365.

    Google Scholar 

  64. Lamouchi, M.; Jeanneau, E.; Novitchi, G.; Luneau, D.; Brioude, A.; Desroches, C. Inorg. Chem. 2014, 53, 63–72.

    Article  CAS  Google Scholar 

  65. Xiong, K.; Wang, X.; Jiang, F.; Gai, Y.; Xu, W.; Su, K.; Li, X.; Yuan, D.; Hong, M. Chem. Commun. 2012, 48, 7456–7458.

    Article  CAS  Google Scholar 

  66. Su, K.; Jiang, F.; Qian, J.; Wu, M.; Xiong, K.; Gai, Y.; Hong, M. Inorg. Chem. 2013, 52, 3780–3786.

    Article  CAS  Google Scholar 

  67. Eliseeva, S. V.; Bünzli, J. C. Chem. Soc. Rev. 2010, 39, 189–227.

    Article  CAS  Google Scholar 

  68. Eliseeva, S. V.; Bünzli, J.-C. G. New J. Chem. 2011, 35, 1165–1176.

    Article  CAS  Google Scholar 

  69. Zhu, X.-H.; Peng, J.; Cao, Y.; Roncali, J. Chem. Soc. Rev. 2011, 40, 3509–3524.

    Article  CAS  Google Scholar 

  70. Liu, Z.; Zhang, G.; Zhang, D. Chem. – Eur. J. 2016, 22, 462–471.

    Google Scholar 

  71. Sabbatini, N.; Guardigli, M.; Manet, I.; Ziessel, R. In Calixarenes 2001; Kluwer Academic Publishers: 2001, p 583–597.

    Google Scholar 

  72. Iki, N.; Horiuchi, T.; Oka, H.; Koyama, K.; Morohashi, N.; Kabuto, C.; Miyano, S. J. Chem. Soc. Perkin Trans. 2001, 2, 2219–2225.

    Article  Google Scholar 

  73. Matsumiya, H.; Masai, H.; Terazono, Y.; Iki, N.; Miyano, S. Bull. Chem. Soc. Jpn. 2003, 76, 133–136.

    Article  CAS  Google Scholar 

  74. Iki, N.; Ohta, M.; Horiuchi, T.; Hoshino, H. Chem. – Asian J. 2008, 3, 849–853.

    Article  CAS  Google Scholar 

  75. Tanaka, T.; Iki, N.; Kajiwara, T.; Yamashita, M.; Hoshino, H. J. Inclusion Phenom. Macrocyclic Chem. 2009, 64, 379–383.

    Article  CAS  Google Scholar 

  76. Iki, N.; Hiro-oka, S.; Tanaka, T.; Kabuto, C.; Hoshino, H. Inorg. Chem. 2012, 51, 1648–1656.

    Article  CAS  Google Scholar 

  77. Iki, N.; Tanaka, T.; Hoshino, H. Inorg. Chim. Acta 2013, 397, 42–47.

    Article  CAS  Google Scholar 

  78. Bünzli, J.-C. G. J. Lumin. 2016, 170, 866–878.

    Google Scholar 

  79. Iki, N.; Hiro-oka, S.; Nakamura, M.; Tanaka, T.; Hoshino, H. Eur. J. Inorg. Chem. 2012, 3541–3545.

    Google Scholar 

  80. Iki, N.; Boros, E.; Nakamura, M.; Baba, R.; Caravan, P. Inorg. Chem. 2016, 55, 4000–4005.

    Google Scholar 

  81. Karashimada, R.; Iki, N. Chem. Commun. 2016, 52, 3139–3142.

    Google Scholar 

  82. Tang, W.; Su, M. Appl. Mech. Mater. 2014, 687–691, 4223–4227.

    Article  Google Scholar 

  83. Song, M.; Sun, Z.; Han, C.; Tian, D.; Li, H.; Kim, J. S. Chem. – Asian J. 2014, 9, 2344–2357.

    Article  CAS  Google Scholar 

  84. Patra, S.; Maity, D.; Gunupuru, R.; Agnihotri, P.; Paul, P. J. Chem. Sci. 2012, 124, 1287–1299.

    Article  CAS  Google Scholar 

  85. Kim, H. N.; Ren, W. X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2012, 41, 3210–3244.

    Article  CAS  Google Scholar 

  86. Sharma, K.; Cragg, P. J. Chem. Sens. 2011, 1, 1–18.

    CAS  Google Scholar 

  87. Ben Ali, M.; Bureau, C.; Martelet, C.; Jaffrezic-Renault, N.; Lamartine, R.; Ben Ouada, H. Mater. Sci. Eng., C 2000, C7, 83–89.

    CAS  Google Scholar 

  88. Ben Ali, M.; Jaffrezic-Renault, N.; Martelet, C.; Ben Ouada, H.; Davenas, J.; Charbonnier, M. Mater. Sci. Eng., C 2001, C14, 17–23.

    Article  CAS  Google Scholar 

  89. Zheng, H.; Yan, Z.; Dong, H.; Ye, B. Sens. Actuators, B 2007, 120, 603–609.

    Article  CAS  Google Scholar 

  90. Wang, L.; Wang, X.; Shi, G.; Peng, C.; Ding, Y. Anal. Chem. 2012, 84, 10560–10567.

    Article  CAS  Google Scholar 

  91. Jin, T.; Fujii, F.; Yamada, E.; Nodasaka, Y.; Kinjo, M. Comb. Chem. High Throughput Screen. 2007, 10, 473–479.

    Article  CAS  Google Scholar 

  92. Hu, X.-J.; Li, C.-M.; Song, X.-Y.; Zhang, D.; Li, Y.-S. Inorg. Chem. Commun. 2011, 14, 1632–1635.

    Article  CAS  Google Scholar 

  93. Horiuchi, T.; Iki, N.; Oka, H.; Miyano, S. Bull. Chem. Soc. Jpn. 2002, 75, 2615–2619.

    Article  CAS  Google Scholar 

  94. Horiuchi, T.; Iki, N.; Hoshino, H. Anal. Chim. Acta 2009, 650, 258–263.

    Article  CAS  Google Scholar 

  95. Iki, N.; Ohta, M.; Tanaka, T.; Horiuchi, T.; Hoshino, H. New J. Chem. 2009, 33, 23–25.

    Article  CAS  Google Scholar 

  96. Abe, N.; Hoshino, H.; Iki, N. Bunseki Kagaku 2015, 64, 493–499.

    Article  CAS  Google Scholar 

  97. Matsumiya, H.; Nakamura, H.; Hiraide, M. Anal. Bioanal. Chem. 2009, 394, 1471–1476.

    Article  CAS  Google Scholar 

  98. Nagai, S.; Matsumiya, H.; Hiraide, M. Bunseki Kagaku 2012, 61, 723–726.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The author acknowledges with thanks Profs. S. Miyano, T. Hattori, and N. Morohashi, Tohoku University for their great suggestions, discussions, and contributions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nobuhiko Iki .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Iki, N. (2016). Thiacalixarenes. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_13

Download citation

Publish with us

Policies and ethics