Interplay between molecular recognition and redox chemistry

Accounts of Chemical Research

Volumn 32, Issue 1, 1999, Pages 62-71

  Kaifer, Angel E ^a  

^a UNIVERSITY OF MIAMI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CYCLODEXTRIN; DENDRIMER;

ARTICLE; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; OXIDATION REDUCTION REACTION; OXIDATION REDUCTION STATE;

EID: 0032964012     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970335u     Document Type: Article

References (74)

1. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives, VCH: Weinheim, 1995.
2. For reviews, see: (a) Beer, P. D. Transition Metal and Organic Redox-Active Macrocycles Designed to Electrochemically Recognize Charged and Neutral Guest Species. Adv. Inorg. Chem. 1992, 39, 79.
3. (b) Fabbrizzi, L.; Poggi, A. Sensors and Switches from Supramolecular Chemistry. Chem. Soc. Rev. 1995, 24, 197.
4. (c) Shinkai, S. Switchable Guest-Binding Receptor Molecules. In Comprehensive Supramolecular Chemistry, Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Elsevier: New York, 1996; Vol. 1, Chapter 18.
5. (d) Kaifer, A. E.; Mendoza, S. Redox-Switchable Receptors. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Elsevier: New York, 1996; Vol. 1, Chapter 19.
6. (e) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Supramolecular Electrochemistry. Angew. Chem., Int. Ed. Engl. 1998, 37, 216.
7. Marcus, R. A. Electron-Transfer Reactions in Chemistry: Theory and Experiment (Nobel Lecture). Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
8. (a) For a recent and comprehensive compilation of work on cyclodextrins, see: Comprehensive Supramolecular Chemistry, Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Elsevier: New York, 1996; Vol. 3.
9. (b) For a review on the applications of cyclodextrins to supramolecular chemistry, see: Wenz, G. Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units. Angew. Chem., Int. Ed. Engl. 1994, 33, 803.
10. Connors, K. A. The Stability of Cyclodextrin Complexes in Solution. Chem. Rev. 1997, 97, 1325.
11. Matsue, T.; Evans, D. H.; Osa, T.; Kobayashi, N. Electron-Transfer Reactions Associated to Host -Guest Complexation. Oxidation of Ferrocenecarboxylixc Acid in the Presence of β-Cyclodextrin. J. Am. Chem. Soc. 1985, 107, 3411.
12. (a) Isnin, R.; Salam, C.; Kaifer, A. E. Bimodal Cyclodextrin Complexation of Ferrocene Derivatives Containing n-Alkyl Chains of Varying Length. J. Org. Chem. 1991, 56, 35.
13. (b) Isnin, R., Kaifer, A. E. Novel Class of Asymmetric Zwitterionic Rotaxanes Based on α-Cyclodextrin. J. Am. Chem. Soc. 1991, 113, 8188.
14. (c) Godínez, L. A.; Patel, S.; Criss, C. M.; Kaifer, A. E. Calorimetric Studies on the Complexation of Several Ferrocene Derivatives by α- and β-Cyclodextrin. Effects of Urea on the Thermodynamic Parameters. J. Phys. Chem. 1995, 99, 17449.
15. (a) Harada, A.; Takahashi, S. Preparation and Properties of Cyclodextrin-Ferrocene Inclusion Complexes. J. Chem. Soc., Chem. Commun. 1984, 645.
16. (b) Thiem, H.-J.; Brandi, M.; Breslow, R. Molecular Modeling Calculations on the Acylation of β-Cyclodextrin by Ferrocenylacrylate Esters. J. Am. Chem. Soc. 1988, 110, 8612.
17. Mirzoian, A.; Kaifer, A. E. Reactive Pseudorotaxanes: Inclusion Complexation of Reduced Viologens by the Hosts β-Cyclodextrin and Heptakis(2,6-di-O-methyl)-β-Cyclodextrin. Chem. Eur. J. 1997, 3, 1052.
18. Wang, Y.; Mendoza, S.; Kaifer, A. E. Electrochemical Reduction of Cobaltocenium in the Presence of β-Cyclodextrin. Inorg. Chem. 1998, 37, 317.
19. Castro, R.; Cuadrado, I.; Alonso, B.; Casado, C. M.; Morán, M.; Kaifer, A. E. Multisite Inclusion Complexation of Redox Active Dendrimer Guests. J. Am. Chem. Soc. 1997, 119, 5760.
20. (a) Gutsche, C. D. In Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: London, 1989.
21. (b) Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
22. Shinkai, S.; Mori, S.; Koreishi, H.; Tsubaki, T.; Manabe, O. Hexasulfonated Calix[6]arene Derivatives: A New Class of Catalysts, Surfactants, and Host Molecules. J. Am. Chem. Soc. 1986, 108, 2409.
23. Zhang, L.; Macías, A.; Lu, T.; Gordon, J. I.; Gokel, G. W.; Kaifer, A. E. Calixarenes as Hosts in Aqueous Media: Inclusion Complexation of Ferrocene Derivatives by a Water-Soluble Calix[6]arene. J. Chem. Soc., Chem. Commun. 1993, 1017.
24. Bernardo, A. R.; Lu, T.; Córdova, E.; Zhang, L.; Gokel, G. W.; Kaifer, A. E. Host-Guest Complexation at the Electrode/Solution Interface: The Inclusion of an Amphiphilic Viologen Guest by an Amphiphilic Calix[6]arene Host. J. Chem. Soc., Chem. Commun. 1994, 529.
25. Castro, A.; Godínez, L. A.; Criss, C. M.; Bott, S. G.; Kaifer, A. E. Solid-State and Solution Complexation of Cobalt(III) Sepulchrate by a Water-Soluble Calix-[6]arene Host. Chem. Commun. 1997, 935.
26. 2O and Its Parent Acid. J. Am. Chem. Soc. 1992, 114, 7558.
27. Alvarez, J.; Wang, Y.; Gómez-Kaifer, M.; Kaifer, A. E. Importance of Intramolecular Hydrogen Bonding for Preorganization and Binding of Molecular Guests by Water-Soluble Calix[6]arene Hosts. Chem. Commun. 1998, 1455.
28. Wang, Y.; Alvarez, J.; Kaifer, A. E. Redox Control of Host-Guest Recognition: A Case of Host Selection Determined by the Oxidation State of the Guest. Chem. Commun. 1998, 1457.
29. Deans, R.; Niemz, A.; Breinlinger, E. C.; Rotello, V. M. Electrochemical Control of Recognition Processes. A Three-Component Molecular Switch. J. Am. Chem. Soc. 1997, 119, 10863.
30. (a) Gómez-Kaifer, M.; Reddy, P. A.; Gutsche, C. D.; Echegoyen, L. Electroactive Calixarenes. 1. Redox and Cation Binding Properties of Calixquinones. J. Am. Chem. Soc. 1994, 116, 3580.
31. (b) Szemes, F.; Hesek, D.; Chen, Z.; Dent, S. W.; Drew, M. G. B.; Goulden, A. J.; Graydon, A. R.; Grieve, A.; Mortimer, R. J.; Wear, T.; Weightman, J. S.; Beer, P. D. Synthesis and Characterization of Novel Acyclic, Macrocyclic and Calix[4]arene Ruthenium(II) Bipyridyl Receptor Molecules that Recognize and Sense Anions. Inorg. Chem. 1996, 35, 5868.
32. Diederich, F. In Cyclophanes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: London, 1990.
33. Seward, E. M.; Hopkins, R. B.; Sauerer, W.; Tam, S.-W.; Diederich, F. Redox-Dependent Binding Ability of a Flavin Cyclophane in Aqueous Solution: Hydrophobic Stacking versus Cavity-Inclusion Complexation. J. Am. Chem. Soc. 1990, 112, 1783.
34. Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Cyclobis-(paraquat-p-phenylene). A Tetracationic Multipurpose Receptor. Angew. Chem., Int. Ed. Engl. 1988, 27, 1547.
35. For recent reviews, see: (a) Amabilino, D. B.; Stoddart, J. F. Interlocked and Intertwined Structures and Superstructures. Chem. Rev. 1995, 95, 2725.
36. (b) Philip, D.; Stoddart, J. F. Self-Assembly in Natural and Unnatural Systems. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
37. (a) Vögtle, F.; Müller, W. M.; Müller, U.; Bauer, M.; Rissamen, K. Photoswitchable Catenanes. Angew. Chem., Int. Ed. Engl. 1993, 32, 1295.
38. (b) Benniston, A. C.; Harriman, A.; Lynch, V. M. Photoactive [2]-Rotaxanes: Structure and Photophysical Properties of Anthracene- and Ferrocene-Stoppered [2]Rotaxanes. J. Am. Chem. Soc. 1995, 117, 5275.
39. (a) Córdova, E.; Bissell, R. A.; Spencer, N.; Ashton, P. R.; Stoddart, J. F.; Kaifer, A. E. Novel Rotaxanes Based on the Inclusion Complexation of Biphenyl Guests by Cyclobis(paraquat-p-phenylene). J. Org. Chem. 1993, 58, 6550.
40. (b) Córdova, E.; Bissell, R. A.; Kaifer, A. E. Synthesis and Electrochemical Properties of Redox-Active [2]Rotaxanes Based on the Inclusion Complexation of 1,4-Phenylenediamine and Benzidine by Cyclobis(paraquat-p-phenylene). J. Org. Chem. 1995, 60, 1033.
41. Mirzoian, A.; Kaifer, A. E. Solvent Effects on the Binding Equilibria between the Guests Indole and Catechol and the Host Cyclobis(paraquat-p-phenylene). J. Org. Chem. 1995, 60, 8093.
42. (b) Castro, R.; Berardi, M.; Córdova, E.; Ochoa de Olza, M.; Kaifer, A. E.; Evanseck, J. Unexpected Roles of Guest Polarizibility and Maximum Hardness, and of Host Solvation in Supramolecular Inclusion Complexes: A Dual Theoretical and Experimental Study. J. Am. Chem. Soc. 1996, 118, 10257.
43. (c) Castro, R.; Nixon, K. R.; Evanseck, J. D.; Kaifer, A. E. Effects of Side Arm Length and Structure of para-Substituted Phenyl Derivatives on Their Binding to the Host Cyclobis(paraquat-p-phenylene). J. Org. Chem. 1996, 61, 7298.
44. Anelli, P. L.; Spencer, N.; Stoddart, J. F. A Molecular Shuttle. J. Am. Chem. Soc. 1991, 113, 5131.
45. Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. A Chemically and Electrochemically Switchable Molecular Shuttle. Nature 1994, 369, 133.
46. Bissell, R. A.; Córdova, E.; Stoddart, J. F.; Kaifer, A. E. Advantages of the Rotaxane Framework for the Construction of Switchable Molecular Devices. In Molecular Engineering for Advanced Materials; Becher, J., Schaumburg, K., Eds.; NATO ASI Series; Kluwer: Dordrecht, The Netherlands, 1995; p 29.
47. For reviews, see: (a) Whitesides, G. M.; Laibinis, P. E. Wet Chemical Approaches to the Characterization of Organic Surfaces: Self-Assembled Monolayers, Wetting, and the Physical-Organic Chemistry of the Solid-Liquid Interface. Langmuir 1990, 6, 87.
48. (b) Ulman, A. Ultrathin Organic Films; Academic Press: New York, 1991; Chapters 3.
49. (c) Dubois, L. H.; Nuzzo, R. G. Synthesis, Structure, and Properties of Model Organic Surfaces. Annu. Rev. Phys. Chem. 1992, 43, 437.
50. (d) Zhong, C.-J.; Porter, M. D. Designing Interfaces at the Molecular Level. Anal. Chem. 1995, 67, 709A.
51. (e) Finklea, H. O. Electrochemistry of Organized Monolayers of Thiols and Related Molecules on Electrodes In Electroanalytical Chemistry, Bard, A. J., Rubinstein, I., Eds.; Marcel Dekker: New York, 1996; Vol. 19, p 109.
52. (a) Rubinstein, I.; Steinberg, S.; Tor, Y.; Shanzer, A.; Sagiv, J. Ionic Recognition and Selective Response in Self-Assembling Monolayer membranes on Electrodes. Nature 1988, 332, 426.
53. (b) Steinberg, S.; Tor, Y.; Sabatini, E.; Rubinstein, I. Ion-Selective Monolayer Membranes Based upon Self-Assembling Tetradentate Ligand Monolayers on Gold Electrodes. 2. Effect of Applied Potential on Ion Binding. J. Am. Chem. Soc. 1991, 113, 5176.
54. (c) Thoden van Velzen, E. U.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W. G.; Reinhoudt, D. N. Self-Assembled Monolayers of Resorcin[4]arene Tetrasulfides on Gold. J. Am. Chem. Soc. 1995, 117, 6853.
55. (d) Schierbaum, K. D.; Weiss, T.; Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N.; Göpel, W. Molecular Recognition by Self-Assembled Monolayers of Cavitand Receptors. Science 1994, 265, 1413.
56. (e) Dermody, D. L.; Crooks, R. M.; Kim, T. Interactions between Organized, Surface-Confined Monolayers and Vapor-Phase Probe Molecules. 11. Synthesis, Characterization, and Chemical Sensitivity of Self-Assembled Polydiacetylene/Calix[n]arene Bilayers. J. Am. Chem. Soc. 1996, 118, 11912.
57. Rojas, M. T.; Kaifer, A. E. Molecular Recognition at the Electrode-Solution Interface. Design, Self-Assembly, and Interfacial Binding Properties of a Molecular Sensor. J. Am. Chem. Soc. 1995, 117, 5883.
58. Rojas, M. T.; Königer, R.; Stoddart, J. F.; Kaifer, A. E. Supported Monolayers Containing Preformed Binding Sites. Synthesis and Interfacial Binding Properties of a Thiolated β-Cyclodextrin Derivative. J. Am. Chem. Soc. 1995, 117, 336.
59. (a) Berg, C. H.; Purcell, E. M. Physics of Chemoreception. Biophys. J. 1977, 20, 193.
60. (b) Shoup, D.; Szabo, A. Role of Diffusion in Ligand Binding to Macromolecules and Cell-Bound Receptors. Biophys. J. 1982, 40, 33.
61. (c) Goldstein, B.; Posner, R. G.; Torney, D. C.; Erickson, J.; Holowka, D.; Baird, B. Competition between Solution and Cell Surface Receptors for Ligand. Biophys. J. 1989, 56, 955.
62. Arias, F.; Godínez, L. A.; Wilson, S. R.; Kaifer, A. E.; Echegoyen, L. Interfacial Hydrogen Bonding. Self-Assembly of a Monolayer of a Fullerene-Crown Ether Derivative on Gold Surfaces Derivatized with an Ammonium-Terminated Alkanethiolate. J. Am. Chem. Soc. 1996, 118, 6086.
63. Lu, T.; Zhang, L.; Gokel, G. W.; Kaifer, A. E. The First Surface-Attached Catenane: Self-Assembly of a Two-Component Monolayer. J. Am. Chem. Soc. 1993, 115, 2542.
64. Zhang, L.; Godínez, L. A.; Lu, T.; Gokel, G. W.; Kaifer, A. E. Molecular Recognition at an Interface: Binding of Monolayer-Anchored Ferrocenyl Groups by an Amphiphilic Calixarene Host. Angew. Chem., Int. Ed. Engl. 1995, 34, 235.
65. Cram, D. J.; Cram, J. M. In Container Molecules and Their Guests; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; Royal Society of Chemistry: Cambridge, MA, 1994; Vol. 4.
66. Mendoza, S.; Davidov, P. D.; Kaifer, A. E. Electrochemistry of Encapsulated Guests: Ferrocene inside Cram's Hemicarcerands. Chem. Eur. J. 1998, 4, 864.
67. For a recent comprehensive monograph, see: Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendritic Molecules: Concepts, Synthesis, and Perspectives; VCH: Weinheim, 1996.
68. Dendrimers containing several electroactive cores have been prepared by other groups: (a) Dandliker, P. J.; Diederich, F.; Gross, M.; Knobler, C. B.; Louati, A.; Sadford, E. M. Dendritic Porphyrins: Modulating Redox Potentials of Electroactive Chromophore with Pendant Multifunctionality. Angew. Chem., Int. Ed. Engl. 1994, 33, 1739.
69. (b) Newkome, G. R.; Guther, R.; Moorefield, C. N.; Cardullo, F.; Echegoyen, L.; Pérez-Cordero, E.; Luftmann, H. Routes to Dendritic Networks: Bis-Dendrimers by Coupling of Cascade Macromolecules through Metal Centers. Angew. Chem., Int. Ed. Engl. 1995, 34, 2023.
70. (c) Dandliker, P. J.; Diederich, F.; Gisselbrecht, J.-P.; Louati, A.; Gross, M. Water-Soluble Iron Porphyrins: Synthetic Models of Globular Heme Proteins. Angew. Chem., Int. Ed. Engl. 1995, 34, 2725.
71. (d) Sadamoto, R.; Tomioka, N.; Aida, T. Photoinduced Electron-Transfer Reactions through Dendrimer Architecture. J. Am. Chem. Soc. 1996, 118, 3978.
72. (e) Bhyrappa, P. Young, J. K.; Moore, J. S.; Suslick, K. S. Dendrimer Metalloporphyrins: Synthesis and Catalysis. J. Am. Chem. Soc. 1996, 118, 5708.
73. (f) Gorman, C. B.; Parkhurst, B. L.; Su, W. Y.; Chen, K.-Y. Encapsulated Electroactive Molecules Based upon an Inorganic Cluster Surrounded by Dendron Ligands. J. Am. Chem. Soc. 1997, 119, 1141.
74. Cardona, C. M.; Kaifer, A. E. Asymmetric Redox-Active Dendrimers Containing a Ferrocene Subunit. Preparation, Characterization, and Electrochemistry. J. Am. Chem. Soc. 1998, 120, 4023.