Site-isolated porphyrin catalysts in imprinted polymers

Chemistry - A European Journal

Volumn 11, Issue 17, 2005, Pages 5055-5061

  Burri, Estelle ^a   Öhm, Margarita ^a   Daguenet, Corinne ^a   Severin, Kay ^a  

^a EPFL   (Switzerland)

Author keywords

Heterogeneous catalysis; Molecular imprinting; Oxidation; Porphyrin complexes; Ruthenium

Indexed keywords

CATALYSIS; COMPLEXATION; METHANE; ORGANIC POLYMERS; OXIDATION; POLYPYRROLES; RUTHENIUM; SYNTHESIS (CHEMICAL);

METALATION; MOLECULAR IMPRINTING; PORPHYRINE; PORPHYRINE COMPLEXES;

CATALYSTS;

EID: 24344435960     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500375     Document Type: Article

References (78)

1. T. Higuchi, H. Ohtake, M. Hirohe, Tetrahedron Lett. 1989, 30, 6545-6548.
2. For reviews see: a) G. Simonneaux, P. Le Maux, Coord. Chem. Rev. 2002, 228, 43-60;
3. b) J. T. Groves, K. Shalyacv, J. Lee in The Porphyrin Handbook, Vol. 4 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 17-40;
4. c) C.-M. Che, W.-Y. Yu, Pure Appl. Chem. 1999, 71, 281-288;
5. d) B. Meunier, Chem. Rev. 1992, 92, 1411-1456.
6. a) C.-M. Che, J.-S. Huang, J.-L. Zhang, C. R. Chim. 2003, 6, 1105-1115;
7. b) J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem. Eur. J. 2002, 8, 1554-1562.
8. a) P. Le Maux, M. Lukas, G. Simonneaux, J. Mol. Catal. A 2003, 206, 95-103;
9. b) A. Berkessel, P. Kaiser, J. Lex. Chem. Eur. J. 2003, 9, 4746-4756;
10. c) R. Zhang, W.-Y. Yu, H.-Z. Sun, W.-S. Liu, C.-M. Che, Chem. Eur. J. 2002, 8, 2495-2507;
11. d) Z. Gross, S. Ini, Org. Lett. 1999, 1, 2077-2080;
12. e) R. Zhang, W.-Y. Yu, T.-S. Lai, C.-M. Che, Chem. Commun. 1999, 409-410;
13. f) Z. Gross, S. Ini, Inorg. Chem. 1999, 38, 1446-1449;
14. g) A. Berkessel, M. Frauenkron, J. Chem. Soc. Perkin Trans. 1 1997. 2265-2266;
15. h) Z. Gross, S. Ini, J. Org. Chem. 1997, 62, 5514-5521;
16. i) Z. Gross, S. Ini, M. Kapon, S. Cohen, Tetrahedron Lett. 1996, 37, 7325-7328.
17. a) R. Zhang, W.-Y. Yu, T.-S. Lai, C.-M. Che, Chem. Commun. 1999, 1791-1792;
18. b) T. Shigeaki, K. Miura, T. Higuchi, M. Hirobe, T. Nagano, Chem. Commun. 1997, 9, 861-862;
19. c) J. T. Groves, M. Bonchio, T. Carofiglio, K. Shalyaev, J. Am. Chem. Soc. 1996, 118, 8961-8962;
20. d) H. Ohtake, T. Higuchi, M. Hirobe, Heterocycles 1995, 40, 867-903;
21. e) H. Ohtake, T. Higuchi, M. Hirobe, J. Am. Chem. Soc. 1992, 114, 10660-10662.
22. R. Ito, N. Umezawa, T. Higuchi, J. Am. Chem. Soc. 2005, 127, 834-835.
23. a) H. Tanaka, K. Hashimoto, K. Suzuki, Y. Kitaichi, M. Sato, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2004, 77, 1905-1914;
24. b) K. Hashimoto, H. Tanaka, T. Ikeno, T. Yamada, Chem. Lett. 2002, 582-583;
25. c) K. Hashimoto, Y. Kitaichi, H. Tanaka, T. Ikeno, T. Yamada, Chem. Lett. 2001, 922-923;
26. d) T. Yamada, K. Hashimoto, Y. Kitaichi, K. Suzuki, T. Ikeno, Chem. Lett. 2001, 268-269;
27. e) J. T. Groves, T. S. Roman, J. Am. Chem. Soc. 1995, 117, 5594-5595.
28. a) H. Tanaka, T. Ikeno, T. Yamada, Synlett 2003, 576-578;
29. b) C. Caris-Veyrat, M.-J. Amiot, R. Ramasseul, J.-C. Marchon, New J. Chem. 2001, 25, 203-206;
30. c) T.-S. Lai, R. Zhang, K.-K. Cheung, H.-L. Kwong, C.-M. Che, Chem. Commun. 1998, 1583-1584;
31. d) E. R. Birnbaum, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chim. Acta 1998, 270, 433-439;
32. c) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792.
33. a) J.-L. Zhang, Y.-L. Liu, C.-M. Che, Chem. Commun. 2002, 2906-2907;
34. b) C.-J. Liu, W.-Y. Yu, S.-G. Li, C.-M. Che, J. Org. Chem. 1998, 63, 7364-7369;
35. c) C.-J. Liu, S.-G. Li, W.-Q. Pang, C.-M. Che, Chem. Commun. 1997, 65-66.
36. R. Zhang, W.-Y. Yu, K.-Y. Wong, C.-Mi. Che, J. Org. Chem. 2001, 66, 8145-8153.
37. C. Paul-Roth, J. Rault-Berthelot, G. Simonneaux, Tetrahedron 2004, 60, 12169-12175.
38. X.-Q. Yu, J.-S. Huang, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2000, 122, 5337-5342.
39. O. Nestler, K. Serverin, Org. Lett. 2001, 3, 3907-3909.
40. For recent monographs about molecular imprinting see: a) Molecularly Imprinted Materials - Science and Technology (Eds.: M. Yan, O. Ramströhm), Marcel Dekker, New York, 2005;
41. b) Molecularly Imprinted Polymers - Man-Made Mimics of Antibodies and Their Applications in Analytical Chemistry (Ed.: B. Sellergren), Elsevier, Amsterdam, 2001.
42. For molecular imprinting with transition-metal catalysts see: a) J. J. Becker, M. R. Gagné, Acc. Chem. Res. 2004, 37, 798-804;
43. b) S. Striegler, J. Chromatogr, B 2004, 804, 183-195;
44. c) M. Tada, Y. Iwasawa, J. Mol. Catal. A 2003, 199, 115-137;
45. d) C. Alexander, L. Davidson, W. Hayes, Tetrahedron 2003, 59, 2025-2057;
46. e) G. Wulff. Chem. Rev. 2002, 102, 1-28;
47. f) K. Severin, Curr. Opin. Chem. Biol. 2000, 4, 710-714.
48. A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour, L. Korsakoff, J. Org. Chem. 1967, 32, 476.
49. H. Eichhorn, M. Sturm, D. Wöhrle, Macromol. Chem. Phys. 1995, 196, 115-131.
50. a) J.-D. Lee, N. T. Greene, G. T. Rushton, K. D. Shimizu, J.-I. Hong, Org. Lett. 2005, 7, 963-966;
51. b) T. Takeuchi, A. Seko, T. Mukawa, Bull. Chem. Soc. Jpn. 2005, 78, 356-360;
52. c) T. Takeuchi, T. Mukawa, J. Matsui, M. Higashi, K. D. Shimizu, Anal. Chem. 2001, 73, 3869-3874;
53. d) J. Matsui, M. Higashi, T. Takeuchi, J. Am. Chem. Soc. 2000, 122, 5218-5219;
54. e) J. Matsui, Y. Tachibana, T. Takeuchi, Anal. Commun. 1998, 35, 225-227.
55. H. Kamogawa, Y. Haramoto, M. Nanasawa, Bull. Chem. Soc. Jpn. 1979, 52, 846-848.
56. J. P. Collman, J. I. Brauman, J. P. Fitzgerald, P. D. Hampton, Y. Naruta, J. W. Sparapany, J. A. Ibers, J. Am. Chem. Soc. 1988, 110. 3477-3486, and references therein.
57. These data are within the expected range. See: B. P. Santora, M. R. Gagné. K. G. Moloy, N. S. Radu, Macromolecules 2001, 34, 658-661.
58. E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, N. Masciocchi, A. Sironi, S. Cenini, Inorg. Chem. 2005, 44, 2039-2049.
59. For additional reports about dimeric μ-oxo-ruthenium-porphyrin complexes see: a) J. P. Collman, C.E. Barnes, P. J. Brothers, T. J. Collins, T. Ozawa, J. C. Gallucci, J. A. Ibers, J. Am. Chem. Soc. 1984, 106, 5151-5163;
60. b) J. P. Collman, C.E. Barnes, T. J. Collins, P. J. Brothers, J. Am. Chem. Soc. 1981, 103, 7030-7032;
61. c) H. Masuda, T. Taga, K. Osaki, H. Sugimoto, M. Mori, H. Ogoshi, J. Am. Chem. Soc. 1981, 103, 2199-2203;
62. d) S. Mosseri, P. Neta, P. Hambright, J. Phys. Chem. 1989, 93, 2358-2362, and references therein.
63. Z. Cheng, L. Zhang, Y. Li, Chem. Eur. J. 2004, 10, 3555-3561.
64. a) K. Chichak, M. C. Walsh, N. R. Branda, Chem. Commun. 2000, 847-848;
65. b) K. Chichak, N. R. Branda, Chem. Commun. 2000, 1211-1212;
66. c) S. L. Darling, C. C. Mark, N. Bampos, N. Feeder, S. J. Teat, J. K. M. Sanders, New J. Chem. 1999, 23, 359-364;
67. d) E. Alessio, S. Geremia, S. Mestroni, E. Iengo, I. Srnova, M. Slouf, Inorg. Chem. 1999, 38, 869-875;
68. e) E. Alessio, S. Geremia, S. Mestroni, I. Srnova, M. Slouf, T. Gianferrara, A. Prodi, Inorg. Chem. 1999, 38, 2527-2529.
69. a) H. Li, L. Nie, S. Yao, Chromatographia 2004, 60, 425-431;
70. b) Y. Lu, C. Li, X. Wang, P. Sun, X. Xing, J. Chromatogr, B 2004, 804, 53-59;
71. c) A. Visnjevski, E. Yilmaz, O. Brüggemann, Appl. Catal. A 2004, 260, 169-174;
72. d) Q. Fu, H. Sanbe, C. Kagawa, K.-K. Kunimoto, J. Haginaka, Anal. Chem. 2003, 75, 191-198.
73. a) K. Polborn, K. Severin, Chem. Eur. J. 2000, 6, 4604-4611;
74. b) K. Polborn, K. Severin, Chem. Commun. 1999, 2481-2482.
75. Selectivity = conversion(2-adamantol)/conversion(2-octanol).
76. a) K. Hyunjung, D. A. Spivak, J. Am. Chem. Soc. 2003, 125, 11269-11275;
77. b) D. A. Spivak, J. Campbell, Analyst 2001, 126, 793-797;
78. c) D. A. Spivak, R. Smon, J. Campbell, Anal. Chim. Acta 2004, 504, 23-30.