DABCO-directed self-assembly of bisporphyrins (DABCO = 1,4-diazabicyclo[2. 2.2]octane)

Chemistry - A European Journal

Volumn 11, Issue 7, 2005, Pages 2196-2206

  Ballester, Pablo ^a,b   Costa, Antoni ^b   Castilla, Ana M ^b   Deyà, Pere M ^b   Frontera, Antonio ^b   Gomila, Rosa M ^b   Hunter, Christopher A ^c  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

^c UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Coordination modes; Porphyrinoids; Receptors; Self assembly; Zinc

Indexed keywords

COMPLEXATION; COORDINATION REACTIONS; ISOMERS; NITROGEN COMPOUNDS; SELF ASSEMBLY; SUBSTITUTION REACTIONS; TITRATION;

AMINOPORPHYRINS; COORDINATION MODES; INTERMOLECULAR ASSEMBLY; POPHYRYNOIDS;

PORPHYRINS;

1,4 DIAZABICYCLO[2.2.2]OCTANE; BISPORPHYRIN DERIVATIVE; CHLOROFORM; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; COVALENT BOND; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; TITRIMETRY; ULTRAVIOLET RADIATION;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHTHALIC ACIDS; PIPERAZINES; PORPHYRINS; SENSITIVITY AND SPECIFICITY; SPECTROPHOTOMETRY, ULTRAVIOLET; TITRIMETRY; ZINC;

EID: 15944363073     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400772     Document Type: Article

References (59)

1. a) P. N. Taylor, H. L. Anderson, J. Am. Chem. Soc. 1999, 121, 11538;
2. b) J. S. Lindsey, New J. Chem. 1991, 15, 153;
3. L. F. Lindoy, I. M. Atkinson, Self-Assembly in Supramolecular Systems, The Royal Society of Chemistry, Cambridge, UK, 2000.
4. B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076;
5. Angew. Chem. Int. Ed. 2001, 40, 2022.
6. S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853.
7. a) C. M. Drain, J. D. Batteas, G. W. Flynn, T. Milic, N. Chi, D. G. Yablon, H. Sommers, Proc. Natl. Acad. Sci. USA 2002, 99, 6498;
8. b) E. Iengo, E. Zangrando, E. Alessio, Eur. J. Inorg. Chem. 2003, 2371;
9. c) J. Wojaczynski, L. Latos-Grazynski, Coord. Chem. Rev. 2000, 204, 113;
10. d) E. Alessio, E. Iengo, L. G. Marzilli, Supramol. Chem. 2002, 14, 103;
11. e) Y. Kobuke, K. Ogawa, Bull. Chem. Soc. Jpn. 2003, 76, 689;
12. f) L. Baldini, C. A. Hunter, Adv. Inorg. Chem. 2002, 55, 213.
13. Examples of assemblies involving a metalloporphyrin unit acting simultaneously as donor and acceptor module: a) See reference [4e];
14. b) H.-J. Kim, N. Bampos, J. K. M. Sanders, J. Am. Chem. Soc. 1999, 121, 8120;
15. c) A. Tsuda, H. Hu, R. Watanabe, T. Aida, J. Porphyrins Phthalocyanines 2003, 7, 388;
16. d) A. Tsuda, S. Sakamoto, K. Yamaguchi, T. Aida, J. Am. Chem. Soc. 2003, 125, 15722.
17. a) R. Takahashi, Y. Kobuke, J. Am. Chem. Soc. 2003, 125, 2372;
18. b) C. Ikeda, N. Nagahara, N. Yoshioka, H. Inoue, New J. Chem. 2000, 24, 897;
19. c) R. A. Haycock, C. A. Hunter, D. A. James, U. Michelsen, L. R. Sutton, Org. Lett. 2000, 2, 2435.
20. a) K. Ogawa, Y. Kobuke, Angew. Chem. 2000, 112, 4236; Angew. Chem. Int. Ed. 2000, 39, 4070;
21. a) K. Ogawa, Y. Kobuke, Angew. Chem. 2000, 112, 4236; Angew. Chem. Int. Ed. 2000, 39, 4070;
22. b) U. Michelsen, C. A. Hunter, Angew. Chem. 2000, 112, 780; Angew . Chem. Int. Ed. 2000, 39, 764;
23. b) U. Michelsen, C. A. Hunter, Angew. Chem. 2000, 112, 780; Angew . Chem. Int. Ed. 2000, 39, 764;
24. c) C. Ikeda, E. Fujiwara, A. Satake, Y. Kobuke, Chem. Commun. 2003, 616.
25. a) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2567;
26. b) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2563;
27. c) G. Ercolani, J. Phys. Chem. B 2003, 107, 5052.
28. a) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169; Angew. Chem. Int. Ed. 1998, 37, 3020;
29. a) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169; Angew. Chem. Int. Ed. 1998, 37, 3020;
30. b) S. Yagi, M. Ezoe, I. Yonekura, T. Takagishi, H. Nakazumi, J. Am. Chem. Soc. 2003, 125, 4068;
31. see also references [1a] and [11].
32. a) C. A. Hunter, R. Tregonning, Tetrahedron 2002, 58, 691;
33. b) L. Baldini, P. Ballester, A. Casnati, R. M. Gomila, C. A. Hunter, F. Sansone, R. Ungaro, J. Am. Chem. Soc. 2003, 125, 14 181.
34. a) H. L. Anderson, C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5780;
35. b) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5773;
36. c) H. L. Anderson, Inorg. Chem. 1994, 33, 972;
37. see also reference [1a].
38. M. Gardner, A. J. Guerin, C. A. Hunter, U. Michelsen, C. Rotger, New J. Chem. 1999, 23, 309.
39. S. B. Lee, J.-I. Hong, Tetrahedron Lett. 1998, 39, 4317.
40. Stoichiometric binding constants for multiple site ligands are related to microscopic binding constants by means of statistical factors. See Figure 2 and reference [20], p. 20.
41. It is generally accepted that intermolecular binding of a divalent receptor (two binding sites) to a monovalent substrate (unique binding site) is positively cooperative if α is larger than 1, it is non-cooperative or statistical if α is equal to 1, and it is negatively cooperative if α is smaller than 1. See reference [20], Chapter 2. α is calculated by dividing the value of the statistically corrected binding constant of the second interaction by that of the first interaction.
42. SPECFIT, Version 3.0 from Spectra Software Associates: a) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1986, 33, 943;
43. b) H. Gampp, M. Maeder, C. J. Meyer, A. D. Zuberbühler, Talanta 1985, 32, 95.
44. 11. In this case, α is calculated by dividing the value of the statistically corrected binding constant of the first interaction by that of the second interaction. The system is said to be positively cooperative if α is smaller than 1.
45. A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454.
46. C. A. Hunter, J. K. M. Sanders, A. J. Stone, Chem. Phys. 1989, 133, 395.
47. K. A. Connors, Binding Constants, Wiley, New York, 1987.
48. a) A. J. Kirby, Adv. Phys. Org. Chem. 1980, 17, 183;
49. b) L. Mandolini, Adv. Phys. Org. Chem. 1986, 22, 1.
50. H. L. Anderson, S. Anderson, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 2231.
51. W. P. Jenks, Catalysis in Chemistry and Enzymology, Dover, New York, 1987.
52. -1 for the stability constant of the ternary complex predict that at 0.5 equivalents of DABCO, the ratio of ternary/sandwich complex should be 15/85, 1/99, and 11/89 for 5 a, 5 b, and 5 c, respectively.
53. 21 = 10.5. These values were used in the simulation of the distribution profile for the destruction of a 3:3 sandwich complex as presented in Figure 11c.
54. Experiments to distinguish the structure of the complexes by ESI mass spectrometry gave only molecular ions corresponding to the free porphyrins. This is a common result for supramolecular assemblies based on the coordination of zinc-oligoporphyrins with aza ligands. All attempts to grow crystals were unsuccessful.
55. H. Zhao, A. Thurkauf, Synth. Commun. 2001, 31, 1921.
56. J. R. Taylor, An Introduction to Error Analysis: The Study of Uncertainty in Physical Measurements, University Science Books, Mill Valley, CA, 1982.
57. M. J. S. Dewar, M. E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902.
58. J. J. P. Stewart, MOPAC-93, Fujitsu, 1993
59. J. Baker, J. Comput. Chem. 1986, 7, 385.