Synthesis and complexation properties of an oligooxaethylene-spacered porphyrin dimer - Toward the construction of a new switchable porphyrin array

European Journal of Organic Chemistry

Volumn , Issue 8, 1999, Pages 1901-1906

  Monti, Donato ^a   Venanzi, Mariano ^a   Mancini, Giovanna ^b   Marotti, Federica ^b   La Monica, Laura ^a   Boschi, Tristano ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Cation binding; Cations; Host guest; Porphyrin receptors; Porphyrinoids; Supramolecular chemistry

Indexed keywords

ETHYLENE DERIVATIVE; PORPHYRIN; PORPHYRIN DERIVATIVE; POTASSIUM; SODIUM;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032792231     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199908)1999:8<1901::AID-EJOC1901>3.0.CO;2-R     Document Type: Article

References (58)

1. [1a] M. R. Wasielewski, Chem. Rev. 1992, 92, 435-461.
2. [1b] H. Kurreck, M. Huber, Angew. Chem. Int. Ed. Engl. 1995, 34, 849-866.
3. [1c] M. D. Ward, Chem. Soc. Rev. 1997, 26, 365-375.
4. [2a] J. Deisenhofer, H. Michel, Science 1989, 245, 1463-1473.
5. [2b] J. Deisenhofer, O. Epp, K. Miki, R. Huber, H. Michel, J. Mol. Biol. 1984, 180, 385-391.
6. [3a] J. P. Collman, P. S. Wagenknecht, J. E. Hutchinson, Angew. Chem. Int. Ed. Engl. 1994, 33, 1537-1554.
7. [3b] J. P. Collman, Inorg. Chem. 1997, 36, 5145-5155.
8. [3c] T. Ayashi, H. Ogoshi, Chem. Soc. Rev. 1997, 26, 355-364.
9. [3d] For an overview of the role of metalloporphyrins as a catalyst in oxidation reactions see: B. Meunier, Chem. Rev. 1992, 92, 1411-1456.
10. [4a] R. Paolesse, P. Tagliatesta, T. Boschi, Tetrahedron Lett. 1996, 37, 2637-2640.
11. [4b] R. Paolesse, R. K. Pandey, T. P. Forsyth, L. Jaquinod, K. R. Gerzevske, D. J. Nurco, M. O. Senge, S. Licoccia, T. Boschi, K. M. Smith, J. Am. Chem. Soc. 1996, 118, 3869-3882.
12. [4c] K. M. Kadish, N. Guo, E. Van Caemelbecke, A. Froiio, R. Paolesse, D. Monti, P. Tagliatesta, T. Boschi, L. Prodi, F. Bolletta, N. Zaccheroni, Inorg. Chem. 1998, 37, 2358-2365.
13. For a critical approach to the problem see for example: T. E. Clement, D. J. Nurco, K. M. Smith, Inorg. Chem. 1998, 37, 1150-1160 and references therein.
14. [6a] U. Hofstra, R. B. M. Koehorst, T. J. Schaafsma, Chem. Phys. Lett. 1986, 130, 555-559.
15. [6b] M. Hugerat, H. Levanon, E. Ojadi, L. Biczok, H. Linschitz, Chem. Phys. Lett. 1991, 181, 400-406.
16. [6c] C. Endisch, J.-H. Fuhrhop, J. Buschmann, P. Luger, U. Siggel, J. Am. Chem. Soc. 1996, 118, 6671-6680.
17. [6d] J. L. Sessler, B. Wang, A. Harriman, J. Am. Chem. Soc., 1995, 117, 704-714.
18. [6e] P. J. F. de Rege, S. A. Williams, M. J. Therien, Science 1995, 269, 1409-1413.
19. [6f] C. M. Drain, K. C. Russell, J.-M. Lehn, Chem. Commun. 1996, 337-338.
20. [6g] L. Cuseck, S. Nagaroja Rao, D. Fitzmaurice, Chem. Eur. J. 1997, 3, 202-207.
21. [6h] Y. Kuroda, A. Kawashima, Y. Hayashi, H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 4929-4933.
22. [6i] L. Flamigni, F. Barigelletti, N. Armaroli, J.-P. Collin, J.-P. Sauvage, J. A. G. Williams, Chem. Eur. J. 1998, 4, 1744-1754.
23. [6l] N. Kariya, T. Imamura, Y. Sasaki, Inorg. Chem. 1998, 37, 1658-1660.
24. [6m] K. Funatsu, T. Imamura, A. Ichimura, Y. Sasaki, Inorg. Chem. 1998, 37, 4986-4995.
25. [6n] N. Kariya, T. Imamura, Y. Sasaki, Inorg. Chem. 1997, 36, 833-839.
26. [6o] H. Yuan, L. Thomas, L. K. Woo, Inorg. Chem. 1996, 35, 2808-2817.
27. [6p] E. Alessio, M. Macchi, S. L. Heath, L. G. Marzilli, Inorg. Chem. 1997, 36, 5614-5623.
28. [6q] C. A. Hunter, L. D. Sarson, Angew. Chem. Int. Ed. Engl. 1994, 33, 2313-2316.
29. [6r] M. Momenteau, F. Le Bras, B. Loock, Tetrahedron Lett. 1994, 35, 3289-3292.
30. For a remarkable example of a mimic of the "special pair" showing high stability in polar solvents see: M. C. Feiters, M. C. T. Fyfe, M.-V. Martinez-Diaz, S. Menzer, R. J. M. Nolte, J. F. Stoddart, P. J. M. van Kan, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 8119-8120.
31. [8a] H.-G. Löhr, F. Vögtle, Acc. Chem. Res. 1985, 18, 65-72.
32. [8b] Y. Kobuke, K. Kokubo, M. Munakata, J. Am. Chem. Soc. 1995, 117, 12751-12758.
33. I. Tabushi, S. Kugimiya, M. G. Kinnaird, T. Sasaki, J. Am. Chem. Soc. 1985, 107, 4192-4199.
34. E. Tsuchida, T. Komatsu, E. Hasegawa, H. Nishide, J. Chem. Soc., Dalton Trans. 1990, 2713-2718.
35. H. Feuer, J. Hooz in The Chemistry of the Ether Linkage, Interscience Publishers, New York, 1967 chapter 10.
36. D. Live, S. Chan, J. Am. Chem. Soc. 1976, 98, 3769-3778.
37. The anisotropic effect of porphyrins is a powerful tool for determining the mutual location of certain protons: T. R. Jonson, J. J. Katz in The Porphyrins (Ed.: D. Dolphin), Academic Press, New York, 1978, vol 4, chapter 1.
38. B. Tümmler, G. Maas, F. Vögtle, H. Sieger, U. Heimann, E. Weber, J. Am. Chem. Soc. 1979, 101, 2588-2598.
39. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534.
40. [16a] For an overview see: W. I. White in The Porphyrins (Ed.: D. Dolphin), Academic Press, New York, 1978, vol. V, chapter 7.
41. [16b] R. F. Pasternack, P. R. Huber. P. Boyd, G. Engasser, L. Francesconi, P. Fasella, G. Cerio Venturo, L. de C. Hinds, J. Am. Chem. Soc. 1972, 94, 4511-4517.
42. For some selected references see: [17a] K. Kano, H. Minamizono, T. Kitae, S. Negi, J. Phys. Chem. A 1997, 101, 6118-6124.
43. [17b] R. Guilard, N. Senglet, Y. H. Liu, D. Sazou, E. Findsen, D. Faure, T. Des Couriers, K. M. Kadish, Inorg. Chem. 1991, 30, 1898-1905 and references therein.
44. P. Laszlo, Angew. Chem. Int. Ed. Engl. 1978, 17, 254-266.
45. J. Grandjean, P. Laszlo, F. Vögtle, H. Sieger, Angew. Chem. Int. Ed. Engl. 1978, 17, 856-857.
46. C. K. Chang, J. Heterocycl. Chem. 1977, 14, 1285-1288.
47. J. R. Lakowicz in Principle of Fluorescence Spectroscopy, Plenum Press, New York, 1983, chapter 9.
48. [22a] R. A. W. Johnstone, M. E. Rose, J. Chem. Soc., Chem. Commun. 1983, 1268-1270.
49. [22b] M. Vincenti, C. Minero, E. Pellizzetti, A. Secchi, E. Dalcanale, Pure Appl. Chem. 1995, 67, 1075-1084.
50. [22c] J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1996, 35, 1090-1093.
51. [22d] M. Lämsä, J. Huuskonen, K. Rissanen, J. Pursiainen, Chem. Eur. J. 1998, 4, 84-92.
52. A quantitative interpretation of the binding constant values by FAB MS, however, is not always straigthforward since the relative peak intensities in some cases do not fully reflect equilibrium conditions. For a useful discussion see for example: G. J. Langley, D. G. Hamilton, M. C. Grossel, J. Chem. Soc., Perkin Trans. 2 1995, 929-933.
53. [24a] L. Fabbrizzi, A. Poggi, Chem. Soc. Rev. 1995, 197-202
54. [24b] A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaughsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566.
55. B. Valuer, J. Boursan, J. Pouget in Fluorescent Chemosensor for Ion and Molecule Recognition (Ed.: A. W. Czarnik), American Chemical Society, Washington DC, 1993, chapter 3.
56. M. Ouchi, Y. Inoue, T. Kanzaki, T. Hakushi, J. Org. Chem. 1984, 49, 1408-1412.
57. D. D. Perrin, W. L. F. Armarego, D. E. Perrin in Purification of laboratory chemicals, 2nd ed., Pergamon Press, New York, 1980.
58. K. A. Connors, Binding Constants -. The Measurement of Molecular Complex Stability, John Wiley & Sons, New York, 1987.