Skip to main content
SpringerLink
Log in

Large Calixarenes

  • Chapter
  • First Online:
Calixarenes and Beyond

Abstract

This chapter deals with those members of the calix[n]arene family having a number n of aryl rings ranging from 7 to 20, which have been defined as the “large” calixarenes. In particular, their synthesis, chemical modification, and supramolecular properties are here reviewed. Notwithstanding their unfavorable common features (the lack of efficient large-scale syntheses, an intricate chemistry, a high conformational mobility, which imply many possible regioisomers with floppy threedimensional shapes) they can be considered useful platforms to construct large hosts for medium-sized organic molecules or metal clusters, or to prepare di- or polytopic receptors, which may present cooperativity or allostery typical of biological systems. The research work here reviewed demonstrates that very interesting results have been already obtained, with recognition properties towards metal and organic cations and different biomolecular targets. Additional applications regard their ability to act as wheels for pseudorotaxane complexes, to stabilize metal clusters, and to give rise to peculiar supramolecular architectures.

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 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. For comprehensive reviews on calixarene macrocycles, see: (a) Gutsche, C. D. Calixarenes, An Introduction; Royal Society of Chemistry: Cambridge, UK, 2008. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713–745. (c) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998. (d) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens J.; Eds.; Kluwer: Dordrecht, 2001. (e) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, UK, 2003; Chapter 19. (f) Calixarenes in the Nanoworld; Vicens J.; Harrowfield, J.; Eds.; Springer, Dordrecht, 2007.

    Google Scholar 

  2. For reviews on the chemistry of large calixarenes, see: (a) ref. 1d; Neri, P.; Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Piattelli, M.; Chapter 5, p. 89─109. (b) Martino, M.; Neri, P. Mini-Rev. Org. Chem. 2004, 1, 219–231.

    Google Scholar 

  3. Munch, J. H.; Gutsche, C. D. Org. Synth. 1990, 68, 243–246.

    Article  CAS  Google Scholar 

  4. (a) Specht, A.; Bernard, P.; Goeldner, M.; Peng, L. Angew. Chem. Int. Ed. 2002, 41, 4706–4708. (b) Martínez-Alanis, P. R.; Castillo, I. Tetrahedron Lett. 2005, 46, 8845─8848. (c) Gaeta, C.; Talotta, C.; Margarucci, L.; Casapullo, A.; Neri, P. J. Org. Chem. 2013, 78, 7627–7638.

    Google Scholar 

  5. (a) Bergougnant, R. D.; Robin, A. Y.; Fromm, K. M. Tetrahedron 2007, 63, 10751–10757. (b) Redshaw, C. Coord. Chem. Rev. 2003, 244, 45─70.

    Google Scholar 

  6. (a) Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Gavuzzo, E.; Neri, P. Org. Lett. 2002, 4, 2649–2652. (b) Gaeta, C.; Talotta, C.; Farina, F.; Camalli, M.; Campi, G.; Neri, P. Chem. Eur. J. 2012, 18, 1219–1230

    Google Scholar 

  7. (a) For the synthesis of p-tert-butylcalix[7]arene by a one-pot procedure, see: Stewart, D. R.; Gutsche, C. D. J. Am. Chem. Soc. 1999, 121, 4136─4146. (b) For the synthesis of p-tert-butylcalix[8]arene by a one-pot procedure, see reference 3.

    Google Scholar 

  8. (a) Kämmerer, H.; Happel, G. Makromol. Chem. 1980, 181, 2049─2062. (b) Hayes, B. T.; Hunter, R. F. J. Appl. Chem. 1958, 8, 743─748. (c) Zetta, L.; Wolff, A.; Vogt, W.; Platt, K. L.; Böhmer, V. Tetrahedron 1991, 47, 1911─1924. (d) Tabatabai, M.; Vogt, W.; Böhmer, V. Tetrahedron Lett. 1990, 31, 3295─3298.

    Google Scholar 

  9. Asfari, Z.; Vicens, J. Makromol. Chem.- Rapid 1989, 10, 181–183.

    Google Scholar 

  10. (a) Casnati, A.; Ferdani, R.; Pochini, A.; Ungaro, R. J. Org. Chem. 1997, 62, 6236─6239. (b) Atwood, J. L.; Hardie, M. J.; Raston, C. L.; Sandoval, C. A. Org. Lett. 1999, 1, 1523─1526.

    Google Scholar 

  11. (a) Gutsche, C. D.; Pagoria P. F. J. Org. Chem. 1985, 50, 5795–5802. (b) Baudry, R.; Felix, C.; Bavoux, C.; Perrin, M.; Vocanson, F.; Dumazet-Bonnamour, I.; Lamartine, R. New J. Chem., 2003, 27, 1540–1543.

    Google Scholar 

  12. Izatt, S. R.; Hawkins, R. T.; Christensen, J. J.; Izatt, R. M. J. Am. Chem. Soc. 1985, 107, 63–66.

    Article  CAS  Google Scholar 

  13. Recently the procedure for the synthesis of 2c has been revised by: Huc, V.; Npetgat, E.; Guérineau, V.; Bourcier, S.; Dos Santos, A.; Guillot, R.; Baltaze, J.-P.; Martini, C. Eur. J. Org. Chem. 2010, 6186–6192.

    Google Scholar 

  14. Lubitov, I. E.; Shokova, E. A.; Kovalev, V. V. Synlett 1993, 647─648.

    Google Scholar 

  15. Falana, O. O.; Keehn, F. M.; Stevenson, R. Tetrahedron Lett. 2015, 3240─3242.

    Google Scholar 

  16. Ferchichi, M.; Jeanneau, E.; Sollier, J.-C.; Meganem, F.; Darbost, U.; Bonnamour, I. CheM 2011, 1, 27–35.

    Article  Google Scholar 

  17. Dumazet, I.; Regnouf De-Vains, J.-B.; Lamartine, R. Synthetic Commun. 1997, 27, 2547–2555.

    Article  CAS  Google Scholar 

  18. Huc, V. G.; Martini, C. PCT Int. Appl. 2014, WO2014033406A120140306.

    Google Scholar 

  19. (a) Columbus, I.; Biali, S. E. Org. Lett. 2007, 9, 2927─2929. (b) Gaeta, C.; Troisi, F.; Martino, M.; Gavuzzo, E.; Neri, P. Org. Lett. 2004, 6, 3027–3030. (c) Troisi, F.; Mogavero, L.; Gaeta, C.; Gavuzzo, E.; Neri, P. Org. Lett. 2007, 9, 915–918. (d) Troisi, F.; Citro, L.; Gaeta, C.; Gavuzzo,E.; Neri P. Org. Lett. 2008, 10, 1393–1396. (e) Gaeta, C.; Troisi, F.; Gavuzzo, E.; Camalli, b M.; Campi, G.; Neri, P. CrystEngComm 2010, 12, 880–887. (f) Gaeta, C.; Troisi, F.; Spagna, R.; Camalli, M.; Campi, G.; Neri, P. CrystEngComm 2011, 13, 467–473.

    Google Scholar 

  20. Shu, C.-M.; Liu, W.-C.; Ku, M.-C.; Tan, F.-S.; Yeh, M.-L.; Lin, L.-G. J. Org. Chem. 1994, 59, 3730–3733. No, K.; Koo, H. J. Bull. Korean Chem. Soc. 1994, 15, 483–488. Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586–601. Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152–3159. Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981, 103, 3782–3792

    Google Scholar 

  21. Martino, M.; Gregoli, L.; Gaeta, C.; Neri, P. Org. Lett. 2002, 4, 1531–1534.

    Article  CAS  Google Scholar 

  22. Jin, T.; Kinjo, M.; Kobayashi, Y.; Hirata, H. J. Chem. Soc., Faraday Trans. 1998, 94, 3135–3140.

    Article  CAS  Google Scholar 

  23. Ludwing, R.; Lentz, D.; Nguyen, T. K. D. Radiochim. Acta 2000, 88, 335–343.

    Google Scholar 

  24. Neri, P.; Battocolo, E.; Cunsolo, F.; Geraci, C.; Piattelli, M. J. Org. Chem. 1994, 59, 3880–3889.

    Article  CAS  Google Scholar 

  25. Cunsolo, F.; Consoli, G. M. L.; Piattelli, M.; Neri, P. J. Org. Chem. 1998, 63, 6852–6858.

    Article  CAS  Google Scholar 

  26. Ferchichi, M.; Jeanneau, E.; Fenet, B.; Meganem, F.; Darbost, U.; Bonnamour, I. Tetrahedron Lett. 2012, 53, 4047–4050.

    Article  CAS  Google Scholar 

  27. (a) Neri, P.; Geraci, C.; Piattelli, M. Tetrahedron Lett. 1993, 34, 3319–3322. (b) Neri, P.; Geraci, C.; Piattelli, M. J. Org. Chem. 1995, 60, 4126–4135. (c) Consoli, G. M. L.; Cunsolo, F.; Piattelli, M.; Neri, P. J. Org. Chem. 1996, 61, 2195–2198.

    Google Scholar 

  28. Cram, D. J. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009–1020.

    Article  Google Scholar 

  29. Cunsolo,F.; Piattelli, M.; Neri, P. J. Chem. Soc., Chem. Commun. 1994, 1917–1918.

    Google Scholar 

  30. For examples of singly bridged calix[7]arene derivatives, see: (a) Martino, M.; Gaeta, C.; Gregoli, L.; Neri, P. Tetrahedron Lett. 2002, 43, 9521–9525. (b) Luo, Z.; Gong, S.; Zhang, C.; Zheng, Q.; Chen, Y. Synlett 2006, 5, 795–797.

    Google Scholar 

  31. Martino, M.; Gaeta, C.; Neri, P. Tetrahedron Lett. 2004, 45, 3387–3391.

    Article  CAS  Google Scholar 

  32. Li, H.; Xiong, D.; Chen, Y.; Xie, P.; Wan, J. J. Incl. Phenom. Macrocycl. Chem. 2008, 60, 169–172.

    Article  CAS  Google Scholar 

  33. Geraci, C.; Piattelli, M.; Chessari, G.; Neri, P. J. Org. Chem. 2000, 65, 5143–5151.

    Article  CAS  Google Scholar 

  34. Gaeta, C.; Gregoli, L.; Martino, M.; Neri, P. Tetrahedron Lett. 2002, 43, 8875–8878.

    Article  CAS  Google Scholar 

  35. (a) Neri, P.; Geraci, C.; Piattelli, M. In: Recent Research Developments in Organic Chemistry; Pandalai, S. G. Ed.; Transworld Research Network, Trivandrum 1997; Vol. 1, p. 285. (b) Geraci, C.; Consoli, G. M. L.; Piattelli, M.; Neri, P. Collect. Czech. Chem. Commun. 2004, 69,1345–1361. (c) Geraci, C.; Piattelli, M.; Neri, P. Tetrahedron Lett. 1996, 37, 3899–3902.

    Google Scholar 

  36. Hernández, D. J.; Castillo, I. Tetrahedron Lett. 2009, 50, 2548–2551.

    Article  Google Scholar 

  37. Hernández, D. J.; Vázquez-Lima, H.; Guadarrama, P.; Martínez-Otero, D.; Castillo, I. Tetrahedron Lett. 2013, 54, 4930–4933.

    Article  Google Scholar 

  38. Geraci, C.; Piattelli, M.; Neri, P. Tetrahedron Lett. 1995, 36, 5429–5432.

    Article  CAS  Google Scholar 

  39. Cunsolo, F.; Consoli, G. M. L.; Piattelli, M.; Neri, P. Tetrahedron Lett. 1996, 37, 715–718.

    Article  CAS  Google Scholar 

  40. Ikeda, A.; Akao, K.; Harada, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 1621–1624.

    Article  Google Scholar 

  41. Geraci, C.; Bottino, A.; Piattelli, M.; Gavuzzo, E.; Neri, P. J. Chem. Soc., Perkin Trans. 2 2000, 185–187.

    Google Scholar 

  42. Gregoli, L.; Russo, L.; Stefio, I.; Gaeta, C.; Arnaud-Neu, F.; Hubscher-Bruder, V.; Khazaeli-Parsa, P.; Geraci, C.; Neri, P. Tetrahedron Lett. 2004, 45, 6277–6281.

    Article  CAS  Google Scholar 

  43. (a) Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Neri, P. Org. Lett. 2001, 3, 1605–1608. (b) Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Gavuzzo, E.; Neri, P. Tetrahedron Lett. 2002, 43, 1209–1211.

    Google Scholar 

  44. Troisi, F.; Gaeta, C.; Neri, P. Tetrahedron Lett. 2005, 46, 8041–8045.

    Article  CAS  Google Scholar 

  45. Gloede, J.; Ozegowski, S.; Matt, D.; De Cian, A. Tetrahedron Lett. 2001, 42, 9139–9142.

    Article  CAS  Google Scholar 

  46. Gloede, J.; Ozegowski, S.; Costisella, B.; Gutsche, C. D. Eur. J. Org. Chem. 2003, 4870–4873.

    Google Scholar 

  47. Li, H.; Zhan, J. J. Incl. Phenom. Macrocycl. Chem. 2008, 60, 379–382.

    Article  CAS  Google Scholar 

  48. Gutsche, C.D. Acc. Chem. Res. 1983, 16, 161–170.

    Article  CAS  Google Scholar 

  49. Verboom, W.; Durie, A.; Egberink, R. J. M.; Asfari, Z.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 1313–1316.

    Article  CAS  Google Scholar 

  50. Gutsche, C. D.; Pagoria, P. F. J. Org. Chem. 1985, 50, 5795–5802.

    Article  CAS  Google Scholar 

  51. Gutsche, C. D.; Lin, L.-G. Tetrahedron 1986, 42, 1633–1640.

    Article  CAS  Google Scholar 

  52. Shinkai, S.; Koreishi, H.; Ueda, K.; Arimura, T.; Manabe, O. J. Am. Chem. Soc. 1987, 109, 6371–6375.

    Article  CAS  Google Scholar 

  53. (a) Cornforth, J. W.; Morgan, E. D.; Potts, K. T.; Rees, R. J. W. Tetrahedron 1973, 29, 1659–1667. (b) Yao, B.; Bassus, J.; Lamartine, R. An. Quim. Int. Ed. 1998, 94, 65–66.

    Google Scholar 

  54. Gutsche, C. D.; Alam, I. Tetrahedron 1988, 44, 4689–4694.

    Article  CAS  Google Scholar 

  55. Gutsche, C. D.; Nam, K. C. J. Am. Chem. Soc. 1988, 110, 6153–6162.

    Article  CAS  Google Scholar 

  56. Bouoit, S.; Bassus, J.; Lamartine, R. An. Quim. Int. Ed. 1998, 94, 342–344.

    Google Scholar 

  57. Dozol, J. F.; Ungaro, R.; Casnati, A. PCT Int. Appl. WO 0112586, 2001 [Chem. Abstr. 2001, 134, 193226].

    Google Scholar 

  58. Gaeta, C.; Caruso, T.; Mincolelli, M.; Troisi, F.; Vasca, E.; Neri, P. Tetrahedron 2008, 64, 5370–5378.

    Article  CAS  Google Scholar 

  59. (a) Podoprygorina, G.; Zhang, J.; Brusko, V.; Bolte, M.; Janshoff, A.; Böhmer, V. Org. Lett. 2003, 5, 5071–5074. (b) Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Mecca, T.; Neri, P. Tetrahedron Lett. 2003, 44, 7467–7470.

    Google Scholar 

  60. Leverd, P. C.; Huc, V.; Palacin, S.; Nierlich, M. J. Incl. Phenom. Macrocycl. Chem. 2000, 36, 259–266.

    Article  CAS  Google Scholar 

  61. Makha, M.; Raston, C. L. Tetrahedron Lett. 2001, 42, 6215–6217.

    Article  CAS  Google Scholar 

  62. Aoki, M.; Nakashima, K.; Kawabata, H.; Tsutsui, S.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1993, 347–354.

    Google Scholar 

  63. (a) Jebors, S.; Ananchenko, G. S.; Coleman, A. W.; Ripmeester, J. A. Tetrahedron Lett. 2007, 48, 5503–5506. (b) Jebors, S.; Fache, F.; Balme, S.; Devoge, F.; Monachino, M.; Cecillon, S.; Coleman, A. W. Org. Biomol. Chem. 2008, 6, 319–329.

    Google Scholar 

  64. Ferro, R.; Tedesco, C.; Gaeta, C.; Neri, P. J. Incl. Phenom. Macrocycl. Chem. 2008, 60, 115–122.

    Article  Google Scholar 

  65. Gaeta, C.; Martino, M.; Neri, P. Tetrahedron Lett. 2003, 44, 9155–9159.

    Article  CAS  Google Scholar 

  66. (a) Troisi, F.; Pierro, T.; Gaeta, C.; Neri, P. Org. Lett. 2009, 11, 697–700. (b) Troisi, F.; Pierro, T.; Carratù, M.; Gaeta, C.; Neri, P. Tetrahedron Lett. 2009, 50, 4416–4419. (c) Talotta, C.; Gaeta, C.; Troisi, F.; Monaco, G.; Zanasi, R.; Mazzeo, G.; Rosini, C.; Neri, P. Org. Lett. 2010, 12, 2912–2915. (d) Chena, S.; Webster, R. D.; Talotta, C.; Troisi, F.; Gaeta, C.; Neri, P. Electrochim. Acta 2010, 55, 7036–7043. (e) Gaeta, C.; Troisi, F.; Talotta, C.; Pierro, T.; Neri, P. J. Org. Chem. 2012, 77, 3634–3639. (f) De Rosa, M.; Soriente, A.; Concilio, G.; Talotta, C.; Gaeta, C.; Neri, P. J. Org. Chem. 2015, 80, 7295–7300. (g) For an exhaustive review on the p-bromodienone route, see: Gaeta, C.; Talotta, C.; Neri, P. J. Incl. Phenom. Macrocycl. Chem. 2014, 79, 23–46.

    Google Scholar 

  67. (a) Kuno, L.; Seri, N.; Biali, S. E. Org. Lett. 2007, 9, 1577–1580. (b) Columbus, I.; Biali, S. E. J. Org. Chem. 2008, 73, 2598–2606. (c) Kogan, K.; Columbus, I.; Biali, S. E. J. Org. Chem. 2008, 73, 7327–7335. (d) Kuno, L.; Biali, S. E. J. Org. Chem. 2011, 76, 3664–3675.

    Google Scholar 

  68. (a) Kogan, K.; Biali, S. E. J. Org. Chem. 2011, 76, 7240–7244. (b) Itzhak, N.; Kogan, K.; Biali, S. E. Eur. J. Org. Chem. 2011, 6581–6585.

    Google Scholar 

  69. Jin, T.; Kinjo, M.; Kobayashi, Y.; Hirata, H. J. Chem. Soc., Faraday Trans. 1998, 94, 3135─3140.

    Google Scholar 

  70. Torrent-Burgues, J.; Vocanson, F.; Perez-Gonzalez, J. J.; Errachid, A. Colloids and Surfaces A: Physicochem. Eng. Aspects 2012, 401, 137–147.

    Google Scholar 

  71. Gaeta, C.; Martino, M.; Neri, P. Org. Lett. 2006, 8, 4409–4412.

    Article  CAS  Google Scholar 

  72. Erra, L.; Tedesco, C.; Vaughan, G.; Brunelli, M.; Troisi, F.; Gaeta, C.; Neri, P. CrystEngComm 2010, 12, 3463–3466.

    Article  CAS  Google Scholar 

  73. Geraci, C.; Chessari, G.; Piattelli, M.; Neri, P. Chem. Commun. 1997, 921–922.

    Google Scholar 

  74. Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Mecca, T.; Neri, P. Tetrahedron Lett. 2003, 44, 7467–7470.

    Article  CAS  Google Scholar 

  75. (a) Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092–2095. (b) Pierro, T.; Gaeta, C.; Talotta, C.; Casapullo, A.; Neri, P. Org. Lett. 2011, 13, 2650–2653. (c) Talotta, C.; Gaeta, C.; Pierro, T.; Neri, P. Org. Lett. 2011, 13, 2098–2101. (d) Talotta, C.; Gaeta, C.; Neri, P. Org. Lett. 2012, 14, 3104–3107. (e) Gaeta, C.; Talotta, C.; Mirra, S.; Margarucci, L.; Casapullo, A.; Neri, P. Org. Lett. 2013, 15, 116–119. (f) Talotta, C.; Gaeta, C.; Qi, Z.; Schalley, C. A.; Neri, P. Angew. Chem. Int. Ed. 2013, 52, 7437–7441. (g) Ciao, R.; Talotta, C.; Gaeta, C.; Margarucci, L.; Casapullo, A.; Neri, P. Org. Lett. 2013, 15, 5694–5697. (h) Ciao, R.; Talotta, C.; Gaeta, Neri, P. Supramol. Chem. 2014, 26, 569–578. (i) Gaeta, C.; Talotta, C.; Neri, P. Chem. Commun. 2014, 50, 9917–9920. (j) Gaeta, C.; Talotta, C.; Farina, F.; Teixeira, F. A.; Marcos, P. A.; Ascenso, J. R.; Neri, P. J. Org. Chem. 2012, 77, 10285–10293.

    Google Scholar 

  76. Jin, T. J. Incl. Phenom. Macrocyclic Chem. 2003, 45, 195–201.

    Article  CAS  Google Scholar 

  77. Pang, T.-T.; Cai, Z.-F.; Liu, H.-L.; Du, L.-M.; Guo, M.-G.; Fu, Y.-L. Anal. Lett. 2014, 47, 1808–1820.

    Article  CAS  Google Scholar 

  78. (a) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229–231. (b) Chen, X.; Boulos, R. A.; Slattery, A. D.; Atwood, J. L.; Raston, C. L. Chem. Commun. 2015, 51, 11413–11416.

    Google Scholar 

  79. Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699–702.

    Google Scholar 

  80. Guzmán-Percástegui; Hernández, D. J.; Castillo, I. Chem. Commun. 2016, 52, 3111–3114.

    Google Scholar 

  81. (a) Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479–2493. (b) Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Soc. Rev. 2007, 36, 254–266. (c) Casnati, A.; Sansone, F.; Ungaro, R. Acc. Chem. Res. 2003, 36, 246–254. (d) Chini, M. G.; Terracciano, S.; Riccio, R.; Bifulco, G.; Ciao, R.; Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 5382–5385. (e) Francese, S.; Cozzolino, A.; Caputo, I.; Esposito, C.; Martino, M.; Gaeta, C.; Troisi, F.; Neri, P. Tetrahedron Lett. 2005, 46, 1611–1615.

    Google Scholar 

  82. (a) Mecca, T.; Consoli, G. M. L.; Geraci, C.; La Spina, R.; Cunsolo, F. Org. Biomol. Chem. 2006, 4, 3763–3768. (b) Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Mecca T. U.S. Patent 7,465,820, 2008.

    Google Scholar 

  83. Mecca, T.; Consoli, G. M. L.; Geraci, C.; Cunsolo, F. Bioorg. Med. Chem. 2004, 12, 5057–5062.

    Google Scholar 

  84. Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Sgarlata, V. Org. Lett. 2004, 6, 4163–4166.

    Article  CAS  Google Scholar 

  85. For exhaustive reviews, see: (a) Perret, F.; Lazar, A. N.; Coleman, A. W. Chem. Commun. 2006, 2425–2438. (b) Guo, D.-S.; Liu, Y. Acc. Chem. Res. 2014, 47, 1925–1934. (c) For a recent report, see: Tauran, Y.; Anjard, C.; Kim, B.; Rhimi, M.; Coleman, A. W. Chem. Commun. 2014, 50, 11404–11406.

    Google Scholar 

  86. Lamartine, R.; Tsukadab, M.; Wilson, D.; Shirata, A. C. R. Chimie 2002, 5, 163–169.

    Article  CAS  Google Scholar 

  87. (a) Kalchenko, O. I.; Perret, F.; Morel-Desrosiers, N.; Coleman, A. W. J. Chem. Soc., Perkin Trans. 2 2001, 258–263. (b) Arena, G.; Contino, A.; Gulino, F. G.; Magri, A.; Sansone, F.; Sciotto, D.; Ungaro, R. Tetrahedron Lett. 1999, 40, 1597–1600.

    Google Scholar 

  88. Da Silva, E.; Ficheux, D.; Coleman, A. W. J. Incl. Phenom. Macrocyclic Chem. 2005, 52, 201–206.

    Article  CAS  Google Scholar 

  89. See Ref. 1f: Gaeta, C.; Tedesco, C.; Neri, P.; Chapter 16, p. 335–354.

    Google Scholar 

  90. Andreetti, G. D.; Ugozzoli, F.; Nakamoto, Y.; Ishida, S.-I. J. Incl. Phenom. Macrocyclic Chem. 1991, 10, 241–253.

    Google Scholar 

  91. Perrin, M.; Lecocq, S.; Asfari, Z. C. R. Acad. Sci. Ser. 2 1990, 310, 515–520.

    CAS  Google Scholar 

  92. Gutsche, C. D.; Gutsche, A. E.; Karaulov, A. I. J. Inclusion Phenom. 1985, 3, 447–451.

    Article  CAS  Google Scholar 

  93. Czugler, M.; Tisza, S.; Speier, G. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 11, 323–331.

    Article  CAS  Google Scholar 

  94. (a) Bergougnant, R. D.; Robin, A. Y.; Fromm, K. M.; Katharina, M. Cryst. Growth Des. 2005, 5, 1691–1694. (b) Dalgarno, S. J.; Hardie, M. J.; Atwood, J. L.; Warren, J. E.; Raston, C. L. New J. Chem. 2005, 29, 649–652. (c) Perret, F.; Bonnard, V.; Danylyuk, O.; Suwinsk, K.; Coleman, A. W. New J. Chem. 2006, 30, 987–990

    Google Scholar 

  95. Liu, Y.; Liao, W.; Bi, Y.; Wang, M.; Wu, Z.; Wang, X.; Su, Z.; Zhang, H. CrystEngComm 2009, 11, 1803–1806.

    Article  CAS  Google Scholar 

  96. Clark, T. E.; Makha, M.; Sobolev, A. N.; Raston, C. L. Dalton Trans. 2008, 4855–4859.

    Google Scholar 

  97. Perrin, M.; Ehlinger, N.; Viola-Motta, L.; Lecocq, S.; Dumazet, I.; Bouoitmontesinos, S.; Lamartine, R. J. Incl. Phenom. Macrocycl. Chem. 2001, 39, 273–276.

    Article  CAS  Google Scholar 

  98. Leverd, P. C.; Dumazet-Bonnamour, I.; Lamartine, R.; Nierlich, M. Chem. Commun. 2000, 493–494.

    Google Scholar 

  99. Bavoux, C.; Baudry, R.; Dumazet-Bonnamour, I.; Lamartine, R.; Perrin, M. J. Incl. Phenom. Macrocycl. Chem. 2001, 40, 221–224.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, Via Giovanni Paolo II, 132, 84084, Fisciano, Salerno, Italy

    Carmen Talotta, Carmine Gaeta, Annunziata Soriente, Margherita De Rosa & Placido Neri

  2. Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, Via Paolo Gaifami 18, 95126, Catania, Italy

    Corrada Geraci

Authors
  1. Carmen Talotta
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Carmine Gaeta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Annunziata Soriente
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Margherita De Rosa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Corrada Geraci
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Placido Neri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Corrada Geraci or Placido Neri .

Editor information

Editors and Affiliations

  1. Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, Fisciano, Salerno, Italy

    Placido Neri

  2. Department of Chemistry, The University of Texas, Austin, Texas, USA

    Jonathan L. Sessler

  3. Department of Chemistry, Tsinghua University, Beijing, China

    Mei-Xiang Wang

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Talotta, C., Gaeta, C., Soriente, A., De Rosa, M., Geraci, C., Neri, P. (2016). Large Calixarenes. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_7

Download citation

Publish with us

Policies and ethics

Search

Navigation