Synthesis and first studies of the host-guest and substrate recognition properties of a porphyrin-tethered calix[6]arene ditopic ligand

European Journal of Organic Chemistry

Volumn , Issue 1, 2011, Pages 166-175

  Monnereau, Cyrille ^a   Rebilly, Jean Noal ^a   Reinaud, Olivia ^a  

^a Laboratoire de Chimie du Solide et Inorganique Moleculaire de Rennes   (France)

Author keywords

Calixarenes; Click chemistry; Coordination modes; Host guest systems; Porphyrinoids; Receptors

Indexed keywords

EID: 78650820829     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001225     Document Type: Article

References (78)

1. A. J. Kirby, Angew. Chem. Int. Ed. Engl. 1996, 35, 706-724.
2. B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947-3980.
3. A. Fersht, Enzyme Structure and Mechanism, 2nd ed., Freeman, San Francisco, 1985.
4. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
5. W. B. Motherwell, M. J. Bingham, Y. Six, Tetrahedron 2001, 57, 4663-4686.
6. See special issue on organic catalysis: Chem. Rev. 2007, 107.
7. H.-C. Liang, M. Dahan, K. D. Karlin, Curr. Opin. Chem. Biol. 1999, 3, 168-175.
8. See special issue on biomimetic inorganic chemistry: Chem. Rev. 2004, 104.
9. See special issue on dioxygen activation by metalloenzymes and models: Acc. Chem. Res. 2007, 40.
10. B. C. Cunningham, J. A. Wells, Curr. Opin. Struct. Biol. 1997, 7, 457-462.
11. M. W. Hosseini, J. M. Lehn, L. Maggiora, K. B. Mertes, M. P. Mertes, J. Am. Chem. Soc. 1987, 109, 537-544.
12. M. L. Merlau, M. del Pilar Mejia, S. T. Nguyen, J. T. Hupp, Angew. Chem. Int. Ed. 2001, 40, 4239-4242.
13. R. G. E. Coumans, J. A. A. W. Elemans, R. J. M. Nolte, A. E. Rowan, Proc. Natl. Acad. Sci. USA 2006, 103, 19647-19651.
14. J. Eid, A. Fehr, J. Gray, K. Luong, J. Lyle, G. Otto, Science 2009, 323, 133-138.
15. S. Shaik, D. Kumar, S. P. de Visser, A. Altun, W. Thiel, Chem. Rev. 2005, 105, 2279-2328.
16. R. R. French, P. P. Holzer, M. G. Leuenberger, W.-D. Woggon, Angew. Chem. Int. Ed. 2000, 39, 1267-1269.
17. P. Thordarson, E. J. A. Bijsterveld, A. E. Rowan, R. J. M. Nolte, Nature 2003, 424, 915-918.
18. Special issue on cyclodextrins: Chem. Rev. 1998, 98, 1741-2076.
19. R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2012.
20. C. D. Gutsche, Calixarenes Revisited, Royal Society of Chemistry, Cambridge, U.K., 1998.
21. R. Cacciapaglia, A. Casnati, L. Mandolini, D. N. Reinhoudt, R. Salvio, A. Sartori, R. Ungaro, J. Org. Chem. 2005, 70, 5398-5402.
22. P. Molenveld, W. M. G. Stikvoort, H. Kooijman, A. L. Spek, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1999, 64, 3896-3906.
23. P. Molenveld, J. F. J. Engbersen, D. N. Reinhoudt, Chem. Soc. Rev. 2000, 29, 75-86.
24. S. Shimizu, N. Shimada, Y. Sasaki, Green Chem. 2006, 8, 608-614.
25. L. Mandolini, R. Ungaro, Calixarenes in Action, Imperial College Press, London, U.K., 2000.
26. C. D. Gutsche, Calixarenes, An Introduction, 2nd ed., Royal Society of Chemistry, Cambridge, U.K., 2008.
27. D. J. Cram, J. M. Cram, Container Molecules and Their Guests, Royal Society of Chemistry, Cambridge, 1994.
28. R. J. Hooley, J. Rebek Jr., Chem. Biol. 2009, 16, 255-264.
29. R. Warmuth, J. Yoon, Acc. Chem. Res. 2001, 34, 95-105.
30. H. Xi, C. L. D. Gibb, B. C. Gibb, J. Org. Chem. 1999, 64, 9286-9288.
31. G. Cevasco, S. Thea, D. Vigo, A. Williams, F. Zaman, J. Phys. Org. Chem. 2006, 19, 630-636.
32. A. Collet, in: Comprehensive Supramolecular Chemistry, vol. 2 (Ed.:, F. Vögtle), Pergamon Press, New York, 1996, pp. 325-365.
33. T. Brotin, J.-P. Dutasta, Chem. Rev. 2008, 109, 88-130.
34. A. Gautier, J.-C. Mulatier, J. Crassous, J.-P. Dutasta, Org. Lett. 2005, 7, 1207-1210.
35. C. D. Gutsche, L. J. Bauer, J. Am. Chem. Soc. 1985, 107, 6052-6059.
36. A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734.
37. J. Vicens, A. Bohmer (Eds.), Topics in Inclusion Science, vol. 3, Kluwer Academic Press, Dordrecht, 1991, p. 280.
38. O. Seneque, M.-N. Rager, M. Giorgi, O. Reinaud, J. Am. Chem. Soc. 2000, 122, 6183-6189.
39. O. Seneque, M.-N. Rager, M. Giorgi, T. Prange, A. Tomas, O. Reinaud, J. Am. Chem. Soc. 2005, 127, 14833-14840.
40. U. Darbost, M.-N. Rager, S. Petit, I. Jabin, O. Reinaud, J. Am. Chem. Soc. 2005, 127, 8517-8525.
41. D. Coquiere, S. Le Gac, U. Darbost, O. Seneque, I. Jabin, O. Reinaud, Org. Biomol. Chem. 2009, 7, 2485-2500.
42. D. Coquiere, J. Marrot, O. Reinaud, Org. Biomol. Chem. 2008, 6, 3930-3934.
43. S. Redon, Y. Li, O. Reinaud, J. Org. Chem. 2003, 68, 7004-7008.
44. D. Coquiére, A. de la Lande, O. Parisel, T. Prangé, O. Reinaud, Chem. Eur. J. 2009, 15, 11912-11917.
45. J. P. Collman, R. Boulatov, C. J. Sunderland, L. Fu, Chem. Rev. 2003, 104, 561-588.
46. E. Rose, B. Andrioletti, S. Zrig, M. Quelquejeu-Ethéve, Chem. Soc. Rev. 2005, 34, 573-583.
47. R. Guilard, K. M. Kadish, Chem. Rev. 2002, 88, 1121-1146.
48. H. Brand, J. Arnold, Coord. Chem. Rev. 1995, 140, 137-168.
49. W.-D. Woggon, Acc. Chem. Res. 2005, 38, 127-136.
50. C. C. Y. Wang, D. M. Ho, J. T. Groves, J. Am. Chem. Soc. 1999, 121, 12094-12103.
51. J. T. Groves, T. E. Nemo, J. Am. Chem. Soc. 1983, 105, 5786-5791.
52. D. Jokic, Z. Asfari, J. Weiss, Org. Lett. 2002, 4, 2129-2132.
53. G. Pognon, C. Boudon, K. J. Schenk, M. Bonin, B. Bach, J. Weiss, J. Am. Chem. Soc. 2006, 128, 3488-3489.
54. J.-P. Tremblay-Morin, S. Faure, D. Samar, C. Stern, R. Guilard, P. D. Harvey, Inorg. Chem. 2005, 44, 2836-2842.
55. D. Mössinger, J. Hornung, S. Lei, S. De Feyter, S. Höger, Angew. Chem. Int. Ed. 2007, 46, 6802-6806.
56. M. O. Senge, X. Feng, J. Chem. Soc. Perkin Trans. 1 2000, 3615-3621.
57. B.-Y. Lee, S. R. Park, H. B. Jeon, K. S. Kim, Tetrahedron Lett. 2006, 47, 5105-5109.
58. N. Jin, M. Ibrahim, T. G. Spiro, J. T. Groves, J. Am. Chem. Soc. 2007, 129, 12416-12417.
59. J. T. Groves, W. J. Kruper, R. C. Haushalter, J. Am. Chem. Soc. 1980, 102, 6375-6377.
60. P. Xue, R. Lu, G. Chen, Y. Zhang, H. Nomoto, M. Takafuji, H. Ihara, Chem. Eur. J. 2007, 13, 8231-8239.
61. P. G. A. Janssen, P. Jonkheijm, P. Thordarson, J. C. Gielen, P. C. M. Christianen, J. L. J. van Dongen, E. W. Meijer, A. P. H. J. Schenning, J. Mater. Chem. 2007, 17, 2654-2660.
62. S. C. M. Gandini, V. E. Yushmanov, I. E. Borissevitch, M. Tabak, Langmuir 1999, 15, 6233-6243.
63. B. Colasson, O. Reinaud, J. Am. Chem. Soc. 2008, 130, 15226-15227.
64. M. Nappa, J. S. Valentine, J. Am. Chem. Soc. 1978, 100, 5075-5080.
65. Note that in the three cases exposed above, we assume that at least one of the two binding constants is large enough to provide full complexation with a stoichiometric amount (or only little excess) of the guest amine: this would not be the case in a diluted medium for host systems displaying only moderate affinity for the guest. See the Supporting Information for more details.
66. H. Tsukube, H. Furuta, A. Odani, Y. Takeda, Y. Kudo, Y. Liu, H. Sakamoto, K. Kimura, in: Comprehensive Supramolecular Chemistry (Eds.:, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J.-M. Lehn, J.-P. Sauvage, M. W. Hosseini), Pergamon Press, Oxford, 1996, p. 425.
67. P. Thordarson, R. G. E. Coumans, J. A. A. W. Elemans, P. J. Thomassen, J. Visser, A. E. Rowan, R. J. M. Nolte, Angew. Chem. Int. Ed. 2004, 43, 4755-4759.
68. G. Ercolani, J. Am. Chem. Soc. 2003, 125, 16097-16103.
69. A. J. Kirby, in: Advances in Physical Organic Chemistry, vol. 17 (Eds.:, V. Gold, D. Bethell), Academic Press, London, 1980, pp. 183-278.
70. L. Mandolini, Adv. Phys. Org. Chem. 1986, 22, 1-111.
71. G. Schwarzenbach, Helv. Chim. Acta 1952, 35, 2344-2359.
72. J. H. Timmons, W. R. Harris, I. Murase, A. E. Martell, Inorg. Chem. 1978, 17, 2192-2197.
73. G. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95-102.
74. A. B. C. Deutman, C. Monnereau, J. A. A. W. Elemans, G. Ercolani, R. J. M. Nolte, A. E. Rowan, Science 2008, 322, 1668-1671.
75. S. P. Gaynor, M. J. Gunter, M. R. Johnston, R. N. Warrener, Org. Biomol. Chem. 2006, 4, 2253-2266.
76. M. J. Crossley, P. Thordarson, Angew. Chem. Int. Ed. 2002, 41, 1709-1712.
77. S. D. Starnes, D. M. Rudkevich, J. Rebek, J. Am. Chem. Soc. 2001, 123, 4659-4669.
78. H. L. Anderson, Inorg. Chem. 1994, 33, 972-981.