Unique inclusion behaviour of 5,11,17,23-tetra-tert-butyl-25,26,27,28- tetraaminothiacalix[4]- Arene towards small organic molecules

Supramolecular Chemistry

Volumn 25, Issue 12, 2013, Pages 812-818

  Morohashi, Naoya ^a   Katagiri, Hiroshi ^a,b   Shimazaki, Takanori ^a   Kitamoto, Yuichi ^a   Tanaka, Shinya ^a   Kabuto, Chizuko ^a   Iki, Nobuhiko ^a   Hattori, Tetsutaro ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

Amino group; Calixarene; Crystallisation; Inclusion; Molecular recognition

Indexed keywords

EID: 84888380103     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610278.2013.806808     Document Type: Article

References (39)

1. Reviews: Gutsche, C.D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J.F., Ed.; The Royal Society of Chemistry, Cambridge, UK, 1998
2. Calixarenes in Action; Mandolini, L.; Ungaro, R., Eds.; Imperial College Press, London, 2000;, pp. 37-61
3. Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.M.; Vicens, J., Eds.; Kluwer Academic Publishers, Dordrecht, 2001, pp. 457-475.
4. Reviews: Lhoták, P. Eur. J. Org. Chem. 2004, 1675-1692
5. Parola, S.; Desroches, C. Collect. Czech. Chem. Commun. 2004, 69, 966-983
6. Morohashi, N.; Narumi, F.; Iki, N.; Hattori, T.; Miyano, S. Chem. Rev. 2006, 106, 5291-5316.
7. For example, see: Sone, T.; Ohba, Y.; Moriya, K.; Kumada, H.; Ito, K. Tetrahedron 1997, 53, 10689-10698
8. Iki, N.; Kabuto, C.; Fukushima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437-1443
9. Ripmeester, J.A.; Enright, G.D.; Ratcliffe, C.I.; Udachin, K.A.; Moudrakovski, I.L. Chem. Commun. 2006, 4986-4996.
10. Yoshimura, K.; Fukazawa, Y. Tetrahedron Lett. 1996, 37, 1435-1438
11. Arena, G.; Contino, A.; Gulino, F.G.; Magri, A.; Sciotto, D.; Ungaro, R. Tetrahedron Lett. 2000, 41, 9327-9330
12. Kon, N.; Iki, N.; Miyano, S. Org. Biomol. Chem. 2003, 1, 751-755
13. Arena, G.; Contino, A.; Longo, E.; Spoto, G.; Arduini, A.; Pochini, A.; Secchi, A.; Massera, C.; Ugozzoli, F. New J. Chem. 2004, 28, 56-61.
14. Wong, P.S.H.; Yu, X-J.; Dearden, D.V. Inorg. Chim. Acta 1996, 246, 259-265
15. Vincenti, M.; Irico, A. Int. J. Mass Spectrom. 2002, 214, 23-36.
16. For example, see: Atwood, J.L.; Barbour, L.J.; Jerga, A.; Schottel, B.L. Science, 2002, 298, 1000-1002
17. Gorbatchuk, V.V.; Tsifarkin, A.G.; Antipin, I.S.; Solomonov, B.N.; Konovalov, A.I.; Lhoták, P.; Stibor, I.J. Phys. Chem. B 2002, 106, 5845-5851
18. Enright, G.D.; Udachin, K.A.; Moudrakovski, I.L.; Ripmeester, J.A. J. Am. Chem. Soc. 2003, 125, 9896-9897
19. Thallapally, P.K.; Mcgrail, B.P.; Dalgarno, S.J.; Schaef, H.T.; Tian, J.; Atwood, J.L. Nat. Mater. 2008, 7, 146-150
20. Morohashi, N.; Noji, S.; Nakayama, H.; Kudo, Y.; Tanaka, S.; Kabuto, C.; Hattori, T. Org. Lett. 2011, 13, 3292-3295
21. Morohashi, N.; Shibata, O.; Hattori, T. Chem. Lett. 2012, 41, 1412-1413.
22. Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699-702.
23. Atwood, J.L.; Koutsantonis, G.A.; Raston, C.L. Nature 1994, 368, 229-231.
24. Katagiri, H.; Iki, N.; Hattori, T.; Kabuto, C.; Miyano, S. J. Am. Chem. Soc. 2001, 123, 779-780.
25. Katagiri, H.; Iki, N.; Matsunaga, Y.; Kabuto, C.; Miyano, S. Chem. Commun. 2002, 2080-2081.
26. Iki, N.; Morohashi, N.; Narumi, F.; Miyano, S. Bull. Chem. Soc. Jpn. 1998, 71, 1597-1603
27. Morohashi, N.; Iki, N.; Sugawara, A.; Miyano, S. Tetrahedron 2001, 57, 5557-5563.
28. Suwattanamala, A.; Magalhães, A.L.; Gomes, J.A.N.F. Chem. Phys. 2005, 310, 109-122
29. Zvereva, E.E.; Katsyuba, S.A.; Vandyukov, A.E.; Chernova, A.V.; Kovalenko, V.I.; Solovieva, S.E.; Antipin, I.S.; Konovalov, A.I. Spectrochim. Acta, A 2010, 75, 872-879.
30. For, D.F.T. calculation of compound 2, see: Katsyuba, S. Kovalenko, V., Chernova, A., Vandyukova, E., Zverev, V., Shagidullin, R., Antipin, I., Solovieva, S., Stoikov, I., Konovalov, A. Org. Biomol. Chem. 2005, 3, 2558-2565.
31. Akdas, H.; Bringel, L.; Graf, E.; Hosseini, M.W.; Mislin, G.; Pansanel, J.; Cian, A.D.; Fischer, J. Tetrahedron Lett. 1998, 39, 2311-2314.
32. Lhoták, P.; Himl, M.; Stibor, I.; Sýkora, J.; Dvořáková, H.; Lang, J. Tetrahedron, 2003, 59, 7581-7585
33. Li, Y.; Yang, W.; Guo, R.; Chen, Y.; Gong, S. Cryst. Eng. Commun. 2012, 14, 1455-1462.
34. Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213
35. Suezawa, H.; Yoshida, T.; Umezawa, Y.; Tsuboyama, S.; Nishio, M. Eur. J. Inorg. Chem. 2002, 3148-3155
36. Nishio, M. Cryst Eng Commun. 2004, 6, 130-158.
37. Sheldrick, G.M. SHELEX-97, Programs for the Refinement of Crystal structures; University of Göttingen: Göttingen, Germany, 1997.
38. Wakita, K. Yadokari-XG, Software for Crystal Structure Analyses, 2001
39. Kabuto, C.; Akine, S.; Nemoto, T.; Kwon, E.J. Cryst. Soc. Jpn. 2009, 51, 218-224.