Self-assembly, binding, and dynamic properties of heterodimeric porphyrin macrocycles

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6616-6622

  Ballester, Pablo ^a   Costa, Antoni ^b   Deyà, Pere M ^b   Frontera, Antonio ^b   Gomila, Rosa M ^b   Oliva, Ana I ^e   Sanders, Jeremy K M ^c   Hunter, Christopher A ^d  

^a INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d UNIVERSITY OF SHEFFIELD   (United Kingdom)

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

Author keywords

[No Author keywords available]

Indexed keywords

MACROMOLECULES; REACTION KINETICS; SELF ASSEMBLY; TITRATION;

HETERODIMERIC TETRALACTUM MACROCYCLES; NONCOVALENT ASSEMBLIES; STABILITY CONSTANTS; TEREPHTHALAMIDE;

PORPHYRINS;

AMIDE; CHLOROFORM; MACROCYCLIC COMPOUND; PORPHYRIN; PORPHYRIN DERIVATIVE; PYRIDINE; ROTAXANE; TEREPHTHALAMIDE; TEREPHTHALIC ACID; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL BINDING; MOLECULAR DYNAMICS; MOLECULAR STABILITY; SELF ASSEMBLY; SYNTHESIS; TITRIMETRY; ULTRAVIOLET RADIATION;

EID: 23644458132     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0505369     Document Type: Article

References (28)

1. (a) Sauvage, J.-P. Molecular Machines and Motors; Springer-Verlag: Berlin, 2001; Vol. 99.
2. (b) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
3. (a) Schalley, C. A.; Beizai, K.; Vögtle, F. Acc. Chem. Res. 2001, 34, 465-476.
4. (b) Bottari, G.; Leigh, D. A.; Perez, E. M. J. Am. Chem. Soc. 2003, 125, 13360-13361 and references therein.
5. Jeong, K.-S.; Choi, J. S.; Chang, S.-Y.; Chang, H.-Y. Angew. Chem., Int. Ed. 2000, 39, 1692-1695.
6. Hunter, C. A.; Low, C. M. R.; Packer, M. J.; Spey, S. E.; Vinter, J. G.; Vysotsky, M. O.; Zonta, C. Angew. Chem., Int. Ed. 2001, 40, 2678-2682.
7. Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313-2316.
8. Markees, D. G.; Kidder, G. W. J. Am. Chem. Soc. 1956, 78, 4130-4135.
9. (a) Lee, S. B.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 4317-4320.
10. (b) Fosdick, L. S.; Fancher, O. E. J. Am. Chem. Soc. 1941, 63, 1277-1279.
11. (c) Calandra, J. C.; Svarz, J. J. J. Am. Chem. Soc. 1950, 72, 1027-1028.
12. Essery, J. M.; Schofield, K. J. Chem. Soc. 1960, 4953-4959.
13. Gardner, M.; Guerin, A. J.; Hunter, C. A.; Michelsen, U.; Rotger, C. New J. Chem. 1999, 23, 309-316.
14. SPECFIT, ver 3.0, from Spectra Software Associates.
15. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 95-101.
16. Anderson, H. L.; Anderson, S.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1995, 2231-2245.
17. The MMFF94 was used as implemented in Macromodel 6.0, except that the charges on the Zn atoms and N atoms coordinated to it were modified. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
18. Differences in the conformation adopted by the bisporphyrins 4a and 4b may cause changes in the geometry of the zinc porphyrin-pyridine interaction contributing also to the observed difference in stability. Gomila, R. M.; Quiñonero, D.; Rotger, C.; Garau, C.; Frontera, A.; Ballester, P.; Costa, A.; Deyà, P. M. Org. Lett. 2002, 4, 399-401.
19. Bisporhyrin 4a is a flexible molecule, for example, about the porphyrin meso bond and so a range of strained conformations are possible for macrocycle 1aa. The structure depicted in Figure 2 is only an energy minimum.
20. Chang, S.-Y.; Um, M.-C.; Uh, H.; Jang, H.-Y.; Jeong, K.-S. Chem. Commun. 2003, 2026-2027.
21. Chang, S.-Y.; Kim, H. S.; Chang, K.-J.; Jeong, K.-S. Org. Lett. 2004, 6, 181-184.
22. Intermolecular NOEs observed in a ROESY experiment on 1aa-8 are also in agreement with a threading binding mode.
23. The small chemical shift difference between the bisporphyrin amide signals of pure 1aa compared with free 1aa in the presence of 10 is probably due to some aggregation at low temperatures.
24. It has been proposed for similar systems that the exchange between the components of the rotaxane occurs by breaking just one coordinative bond (see refs 3 and 4), but no determination of the rate constant for the exchange of the subunits of the self-assembled macrocycle has been carried out.
25. Pons, M.; Millet, O. Prog. Nucl. Magn. Reson. Spectrosc. 2001, 38, 267-324.
26. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90 (6), 935-67.
27. D2DNMR (PC version).
28. Abel, E. W.; Coston, T. P. J.; Orrell, K. G.; Sik, V.; Stephenson, D. J. Magn. Reson. 1986, 70 (1), 34-53.