Head-to-Head Linked Double Calix[4]arenes: Convenient Synthesis and Complexation Properties

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2487-2493

  Struck, Oliver ^a   Chrisstoffels, Lysander A J ^a   Lugtenberg, Ronny J W ^a   Verboom, Willem ^a   Van Hummel, Gerrit J ^a   Harkema, Sybolt ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000763140     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962138z     Document Type: Article

References (60)

1. Resorcinarenes and calix[4]arenes: (a) Timmerman, P.; Nierop, K.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132. (b) Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 5920.
2. Resorcinarenes and calix[4]arenes: (a) Timmerman, P.; Nierop, K.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132. (b) Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 5920.
3. Porphyrins and calix[4]arenes: (a) Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1994, 35, 7131. (b) Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6585.
4. Porphyrins and calix[4]arenes: (a) Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1994, 35, 7131. (b) Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6585.
5. Cyclodextrins and calix[4]arenes: (a) van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151. (b) van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Grote Gansey, M. H. B.; Venema, F.; Feiters, M. C.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6537.
6. Cyclodextrins and calix[4]arenes: (a) van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151. (b) van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Grote Gansey, M. H. B.; Venema, F.; Feiters, M. C.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6537.
7. (a) For a recent review, see: Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
8. (b) Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry, Vol. 1; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989.
9. (c) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens. J., Böhmer, V., Eds.; Kluwer Academic Press: Dordrecht, 1991.
10. For a recent review on covalently linked double calix[4]arenes, see: Asfari, Z.; Weiss, J.; Vicens, J. Synlett 1993, 719.
11. Siepen, A.; Zett, A.; Vögtle, F. Liebigs Ann. 1996, 757.
12. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1995, 60, 6070.
13. Double calix[4]arenes linked via polymethene spacers were reported by Böhmer et al. The authors used a stepwise synthesis in which the calix[4]arene skeleton was built up in the final step. The reported yields are very low (1-13%): Böhmer, V.; Goldmann, H.; Vogt, W.; Vicens, J.; Asfari, Z. Tetrahedron Lett. 1989, 30, 1391.
14. The synthesis of a symmetric double calix[4]arene (12% yield) covalently linked via four ethylene glycol spacers at the upper rim was described by Shinkai et al.: Araki, K.; Sisido, K.; Hisaichi, K.; Shinkai, S. Tetrahedron Lett. 1993, 34, 8297.
15. 2-bridged double calix[4]arene via the upper rim was recently reported: Araki, K.; Hisaichi, K.; Kanai, T.; Shinkai, S. Chem. Lett. 1995, 569.
16. 2 bridges: Arduini, A.; Fanni, S.; Manfredi, G.; Pochini, A.; Ungaro, R.; Sicuri, A. R.; Ugozzoli, F. J. Org. Chem. 1995, 60, 1448.
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26. Arduini, A.; Fabbi, M.; Mantovani, M.; Mirone, L.; Pochini, A.; Secchi, A.; Ungaro, R. J. Org. Chem. 1995, 60, 1454.
27. 1H NMR and the FAB-MS spectra.
28. For the stabilization of the cone conformation of calix[4]arenes via proximal OH⋯OR hydrogen bonds at the lower rim, see for example: Bugge, K.-E.; Verboom, W.; Reinhoudt, D. N.; Harkema, S. Acta Crystallogr. 1992, C48, 1848.
29. 1H NMR spectrum of a 4-week- old sample showed decomposition of 10. Also diamine 3 decomposed (oxidation) by contact with air.
30. 3CN in THF as a solvent resulted in many side products. Double calix[4]-arene 11 could be isolated only in low yield (<10%) after several purification steps.
31. b is possible due to the longer distance.
32. For very recent discussions on the pinched cone conformation of calix[4]arenes in solution, see refs 17b and 25.
33. Scheerder, J.; Vreekamp, R. H.; Engbersen, J. F. J.; Verboom, W.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 3476.
34. b and the imine proton absorb at the usual, lower field.
35. For the first X-ray crystal structure of a self-assembled, hydorogen-bonded calix[4]arene dimer via the upper rim, see ref 17b.
36. An X-ray structure of a double calix[4]arene in the 1,3-alternate conformation was very recently reported by de Mendoza et al. The authors also described qualitative studies of silver(I) ion complexation: Pérez-Adelmar, J.-A.; Abraham, H.; Sánchez, C.; Rissanen, K.; Prados, P.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1009.
37. 2- bridged double calix[4]arene, see ref 10 and literature cited therein.
38. The solubility of double calix[4]arene 8 in the membrane matrix (o-NPOE) is limited; therefore, the more soluble double calix[4]arene 9 was used for the membrane transport studies.
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47. Casabó et al. showed already that simple thioethers could be applied in CHEMFETs as good sensing molecules. (a) Casabó, J.; Flor, T.; Romero, M. I.; Teixidor, F.; Pérez-Jiménez, C. Anal. Chim. Acta 1994, 294, 207. (b) Errachid, A.; Bausells, J.; Merlos, A.; Esteve, J.; Teixidor, F.; Pérez-Jiménez, C.; Casabó, J.; Jiménez, C.; Bartrolí, J. Sens. Actuators B 1995, 26-27, 321.
48. Casabó et al. showed already that simple thioethers could be applied in CHEMFETs as good sensing molecules. (a) Casabó, J.; Flor, T.; Romero, M. I.; Teixidor, F.; Pérez-Jiménez, C. Anal. Chim. Acta 1994, 294, 207. (b) Errachid, A.; Bausells, J.; Merlos, A.; Esteve, J.; Teixidor, F.; Pérez-Jiménez, C.; Casabó, J.; Jiménez, C.; Bartrolí, J. Sens. Actuators B 1995, 26-27, 321.
49. Also more lipophilic thioethers have been described. Wróblewski, W.; Brzózka, Z. Sens. Actuators B 1995, 26-27, 183.
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51. 13C NMR spectrum could be obtained.
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59. The authors have deposited atomic coordinates for compound 11 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1 EZ, U.K.
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