Solvent-induced high fidelity switching between two discrete supramolecules

Journal of the American Chemical Society

Volumn 131, Issue 9, 2009, Pages 3186-3188

  Betancourt, José E ^a   Martín Hidalgo, Mariana ^a   Gubala, Vladimir ^a   Rivera, José M ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; BIOMOLECULES; POTASSIUM IODIDE;

GUANOSINES; HIGH FIDELITY; MECHANISM OF FORMATION; NANOCONSTRUCTION; OCTAMERS; POTASSIUM CONCENTRATIONS; SELF ASSEMBLED STRUCTURES; SELF-ASSEMBLED; SOLVENT EFFECTS; STERIC CROWDING; SUPRAMOLECULES; SWITCHING PROCESS; TETRAMERS;

POTASSIUM;

CADMIUM CHLORIDE; GUANOSINE; POTASSIUM IODIDE; SOLVENT; TETRAMER; ACETONITRILE DERIVATIVE; CHLOROFORM; MACROMOLECULE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; MOLECULE; PROTON NUCLEAR MAGNETIC RESONANCE; ANALOGS AND DERIVATIVES; CHEMISTRY; MACROMOLECULE; SYNTHESIS;

ACETONITRILES; CHLOROFORM; GUANOSINE; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MOLECULAR STRUCTURE; SOLVENTS;

EID: 67849085529     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja809612d     Document Type: Article

References (35)

1. (a) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines - A Journey into the Nano World; Wiley-VCH: Weinheim, 2003.
2. (b) Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, 2001.
3. (c) Feringa, B. L. J. Org. Chem. 2007, 72, 6635-6652.
4. Balzani, V.; Credi, A.; Venturi, M. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 4814-4817.
5. Moon, K.; Kaifer, A. E. J. Am. Chem. Soc. 2004, 126, 15016-15017.
6. (a) Pieraccini, S.; Masiero, S.; Pandoli, O.; Samori, P.; Spada, G. P. Org. Lett. 2006, 8, 3125-3128.
7. (b) Ghoussoub, A.; Lehn, J. M. Chem. Commun. 2005, 46, 5763-5765.
8. For examples of discrete coordination-driven assemblies that reversibly interconvert by varying the ratio of metal to ligand, see a-b; for those that interconvert by changing the solvent see, c-d. (a) From dimers to tetramers: Hiraoka, S.; Yi, T.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2002, 124, 14510-14511.
9. (b) From tetramers to octamers: Harano, K.; Hiraoka, S.; Shionoya, M. J. Am. Chem. Soc. 2007, 129, 5300-5301.
10. (c) Suzuki, K.; Kawano, M.; Fujita, M. Angew. Chem., Int. Ed. 2007, 46, 2819-2822.
11. (d) Provent, C.; Rivara-Minten, E.; Hewage, S.; Brunner, G.; Williams, A. Chem.-Eur. J. 1999, 5, 3487-3494.
12. (a) Davis, J. T.; Spada, G. P. Chem. Soc. Rev. 2007, 36, 296-313.
13. (b) Davis, J. T. Angew. Chem., Int. Ed. 2004, 43, 668-698.
14. (a) Gubala, V.; Betancourt, J. E.; Rivera, J. M. Org. Lett. 2004, 6, 4735-4738.
15. (b) Gubala, V.; De Jesús, D.; Rivera, J. M. Tetrahedron Lett. 2006, 47, 1413-1416.
16. (a) García-Arriga, M.; Hobley, G.; Rivera, J. M. J. Am. Chem. Soc. 2008, 130, 10492-10493.
17. (b) Betancourt, J. E.; Rivera, J. M. Org. Lett. 2008, 10, 2287-2290.
18. See Supporting Information.
19. (a) Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554.
20. (b) Kaucher, M. S.; Lam, Y. F.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. Chem.-Eur. J. 2004, 11, 164-173.
21. H = 9.96 Å.
22. 16·3KI.
23. The Hill coefficient should be viewed not just as a lower end on the number of binding sites in a receptor but as an "interaction coefficient" that indicates the level of cooperativity in a system, Weiss, J. N. FASEB J. 1997, 11, 835-841.
24. The use of Hill coefficients as a measure of cooperativity in self-assembly should only be used when all the stepwise constants refer to identical intermolecular processes: Ercolani, G. J. Am. Chem. Soc. 2003, 125, 16097-16103.
25. García-Arriga, M.; Hobley, G.; Rivera, J. M. Unpublished results.
26. N = 0.460) enhancing the activity (and solubility) of individual ions by preventing their association. For more details, see SI p. S17 and Reichardt, C. Solvent and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003.
27. -, increases as the interatomic distance decreases. For more details, see ref 9.
28. (a) Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Susalito, CA, 2006.
29. (b) Dill, K. A.; Bromberg, S. Molecular Driving Forces: Statistical Thermodynamics in Chemistry and Biology; Garland Science: New York & London, 2002.
30. Rivera, J. M.; Craig, S. L.; Martin, T.; Rebek, J. Angew. Chem., Int. Ed. 2000, 39, 2130-2132.
31. 3CN by EXSY NMR, is 66.7 s. For more details, see Figure S13 and Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
32. For a detailed study on the differential affinity for cations in lipophilic G-quadruplexes, see: Ma, L.; Iezzi, M.; Kaucher, M. S.; Lam, Y. F.; Davis, J. T. J. Am. Chem. Soc. 2006, 128, 15269-15277.
33. The residence lifetime for the potassium cations in the G-quadruplex structure formed by 5′-GMP has been estimated at 250 ms. (a) Wong, A.; Ida, R.; Wu, G. Biochem. Biophys. Res. Commun. 2005, 337, 363-366.
34. (b) Ida, R.; Wu, G. J. Am. Chem. Soc. 2008, 130, 3590-3602.
35. (c) Neidle, S.; Balasubramanian, S. Quadruplex Nucleic Acids; The Royal Society of Chemistry: Cambridge, 2006.