Kinetic and thermodynamic approaches for the efficient formation of mechanical bonds

Accounts of Chemical Research

Volumn 41, Issue 12, 2008, Pages 1750-1761

  Dichtel, William R ^a,b   Miljanić, Ognjen Š ^a   Zhang, Wenyu ^a   Spruell, Jason M ^a,c   Patel, Kaushik ^a,c   Aprahamian, Ivan ^a   Heath, James R ^b   Stoddart, J Fraser ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b California Institute of Technology   (United States)

^c NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149098875     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800067h     Document Type: Article

References (43)

1. Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. A 160-Kilobit Molecular Electronic Memory Patterned at 10(11) Bits Per Square Centimetre. Nature 2007, 445, 414-417.
2. Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. A [2]Catenane Made to Order. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399.
3. Choi, J. W.; Flood, A. H.; Steuerman, D. W.; Nygaard, S.; Braunschweig, A. B.; Moonen, N. N. P.; Laursen, B. W.; Luo, Y.; DeIonno, E.; Peters, A. J.; Jeppesen, J. O.; Xu, K.; Stoddart, J. F.; Heath, J. R. Ground-State Equilibrium Thermodynamics and Switching Kinetics of Bistable [2]Rotaxanes Switched in Solution, Polymer Gels, and Molecular Electronic Devices. Chem. Eur. J. 2006, 12, 261-279.
4. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
5. Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 2002, 67, 3057-3064.
6. Dichtel, W. R.; Miljanić , O.Š.; Spruell, J. M.; Heath, J. R.; Stoddart, J. F. Efficient Templated Synthesis of Donor-Acceptor Rotaxanes Using Click Chemistry. J. Am. Chem. Soc. 2006, 128, 10388-10390.
7. Lutz, J. F. 1,3-Dipolar Cycloadditions of Azides and Alkynes: A Universal Ligation Tool in Polymer and Materials Science. Angew. Chem., Int. Ed. 2007, 46, 1018-1025.
8. Kolb, H. C.; Sharpless, K. B. The Growing Impact of Click Chemistry on Drug Discovery. Drug Discovery Today 2003, 8, 1128-1137.
9. Mobian, P.; Collin, J.-P.; Sauvage, J.-P. Efficient Synthesis of a Labile Copper(I)-Rotaxane Complex Using Click Chemistry. Tetrahedron Lett. 2006, 47, 4907-4909.
10. Aucagne, V.; Hanni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. Catalytic "Click" Rotaxanes: A Substoichiometric Metal-Template Pathway to Mechanically Interlocked Architectures. J. Am. Chem. Soc. 2006, 128, 2186-2187.
11. Miljanić, O.Š.; Dichtel, W. R.; Mortezaei, S.; Stoddart, J. F. Cyclobis(paraquat-pphenylene)-Based [2]Catenanes Prepared by Kinetically Controlled Reactions Involving Alkynes. Org. Lett. 2006, 8, 4835-4838.
12. Miljanić, O.Š.; Dichtel, W. R.; Khan, S. I.; Mortezaei, S.; Heath, J. R.; Stoddart, J. F. Structural and Co-Conformational Effects of Alkyne-Derived Subunits in Charged Donor-Acceptor 2 Catenanes. J. Am. Chem. Soc. 2007, 129, 8236-8246.
13. Siemsen, P.; Livingston, R. C.; Diederich, F. Acetylenic Coupling: A Powerful Tool in Molecular Construction. Angew. Chem., Int. Ed. 2000, 39, 2633-2657.
14. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Dynamic Covalent Chemistry. Angew. Chem., Int. Ed. 2002, 41, 898-952.
15. Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J. L.; Sanders, J. K. M.; Otto, S. Dynamic Combinatorial Chemistry. Chem. Rev. 2006, 106, 3652-3711.
16. Miljanić, O.Š.; Stoddart, J. F. Dynamic Donor-Acceptor [2]Catenanes. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 12966-12970.
17. D'Acerno, C.; Doddi, G.; Ercolani, G.; Mencarelli, P. Template Effects and Kinetic Selection in the Self-Assembly of Crown Ether Cyclobis(Paraquat- PPhenylene) 2 Catenanes - Effect of the 1,4-Dioxybenzene and 1,5-Dioxynaphthalene Units. Chem. Eur. J. 2000, 6, 3540-3546.
18. Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montalti, M.; Shipway, A. N.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Venturi, M.; White, A. J. P.; Williams, D. J. A Chemically and Electrochemically Switchable [2]Catenane Incorporating a Tetrathiafulvalene Unit. Angew. Chem., Int. Ed. 1998, 37, 333-337.
19. Asakawa, M.; Ashton, P. R.; Menzer, S.; Raymo, F. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Cyclobis(Paraquat-4,4′-Biphenylene) - an Organic Molecular Square. Chem. Eur. J. 1996, 2, 877-893.
20. Patel, K.; Miljanić, O.Š.; Stoddart, J. F. Iodide-Catalysed Self-Assembly of Donor-Acceptor [3]Catenanes. Chem. Commun. 2008, 1853-1855.
21. Liu, Y.; Flood, A. H.; Bonvallett, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C. M.; Stoddart, J. F. Linear Artificial Molecular Muscles. J. Am. Chem. Soc. 2005, 127, 9745-9759.
22. Aucagne, V.; Leigh, D. A. Chemoselective Formation of Successive Triazole Linkages in One Pot: "Click-Click" Chemistry. Org. Lett. 2006, 8, 4505-4507.
23. Orsini, A.; Viterisi, A.; Bodlenner, A.; Weibel, J. M.; Pale, P. A Chemoselective Deprotection of Trimethylsilyl Acetylenes Catalyzed by Silver Salts. Tetrahedron Lett. 2005, 46, 2259-2262.
24. Spruell, J. M.; Dichtel, W. R.; Heath, J. R.; Stoddart, J. F. A One-Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential Cu(I)-Catalyzed Azide-Alkyne Cycloadditions. Chem. Eur. J. 2008, 14, 1468-1477.
25. Braunschweig, A. B.; Dichtel, W. R.; Miljanić, O.Š.; Olson, M. A.; Spruell, J. M.; Khan, S. I.; Heath, J. R.; Stoddart, J. F. Modular Synthesis and Dynamics of a Variety of Donor-Acceptor Interlocked Compounds Prepared by Click Chemistry. Chem. Asian J. 2007, 2, 634-647.
26. Kang, S. S.; Vignon, S. A.; Tseng, H.-R.; Stoddart, J. F. Molecular Shuttles Based on Tetrathiafulvalene Units and 1,5-Dioxynaphthalene Ring Systems. Chem. Eur. J. 2004, 10, 2555-2564.
27. Aprahamian, I.; Dichtel, W. R.; Ikeda, T.; Heath, J. R.; Stoddart, J. F. A Clicked Bistable [2]Rotaxane. Org. Lett. 2007, 9, 1287-1290.
28. Steuerman, D. W.; Tseng, H.-R.; Peters, A. J.; Flood, A. H.; Jeppesen, J. O.; Nielsen, K. A.; Stoddart, J. F.; Heath, J. R. Molecular-Mechanical Switch-Based Solid-State Electrochromic Devices. Angew. Chem., Int. Ed. 2004, 43, 6486-6491.
29. Tseng, H.-R.; Wu, D. M.; Fang, N. X. L.; Zhang, X.; Stoddart, J. F. The Metastability of an Electrochemically Controlled Nanoscale Machine on Gold Surfaces. ChemPhysChem 2004, 5, 111-116.
30. Aprahamian, I.; Yasuda, T.; Ikeda, T.; Saha, S.; Dichtel, W. R.; Isoda, K.; Kato, T.; Stoddart, J. F. A Liquid-Crystalline Bistable [2]Rotaxane. Angew. Chem., Int. Ed. 2007, 46, 4675-4679.
31. Eelkema, R.; Pollard, M. M.; Vicario, J.; Katsonis, N.; Ramon, B. S.; Bastiaansen, C. W. M.; Broer, D. J.; Feringa, B. L. Nanomotor Rotates Microscale Objects. Nature 2006, 440, 163-163.
32. Zhang, W.; Dichtel, W. R.; Steig, A. Z.; Benítez, D.; Gimzewski, J. K.; Heath, J. R.; Stoddart, J. F. Folding in a Donor-Acceptor Polyrotaxane Using Secondary Noncovalent Interactions. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 6514-6519.
33. Wenz, G.; Han, B. H.; Müller, A. Cyclodextrin Rotaxanes and Polyrotaxanes. Chem. Rev. 2006, 106, 782-817.
34. Whang, D.; Jeon, Y. M.; Heo, J.; Kim, K. Self-Assembly of a Polyrotaxane Containing a Cyclic "Bead" in Every Structural Unit in the Solid State: Cucurbituril Molecules Threaded on a One-Dimensional Coordination Polymer. J. Am. Chem. Soc. 1996, 118, 11333-11334.
35. Lokey, R. S.; Iverson, B. L. Synthetic Molecules That Fold into a Pleated Secondary Structure in Solution. Nature 1995, 375, 303-305.
36. Appella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X. L.; Barchi, J. J.; Gellman, S. H. Residue-Based Control of Helix Shape in Beta-Peptide Oligomers. Nature 1997, 387, 381-384.
37. Hill, D. J.; Moore, J. S. Helicogenicity of Solvents in the Conformational Equilibrium of Oligo(m-phenylene ethynylene)s: Implications for Foldamer Research. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5053-5057.
38. Lummerstorfer, T.; Hoffmann, H. Click Chemistry on Surfaces: 1,3-Dipolar Cycloaddition Reactions of Azide-Terminated Monolayers on Silica. J. Phys. Chem. B 2004, 108, 3963-3966.
39. Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. "Clicking" Functionality onto Electrode Surfaces. Langmuir 2004, 20, 1051-1053.
40. Rohde, R. D.; Agnew, H. D.; Yeo, W. S.; Bailey, R. C.; Heath, J. R. A Non-Oxidative Approach toward Chemically and Electrochemically Functionalizing Si(111). J. Am. Chem. Soc. 2006, 128, 9518-9525.
41. Patel, K.; Angelos, S.; Dichtel, W. R.; Coskun, A.; Yang, Y.-W.; Zink, J. I.; Stoddart, J. F. Enzyme-Responsive Snap-Top Covered Silica Nanocontainers. J. Am. Chem. Soc. 2008, 130, 2382-2383.
42. Rozkiewicz, D. I.; Janczewski, D.; Verboom, W.; Ravoo, B. J.; Reinhoudt, D. N. "Click" Chemistry by Microcontact Printing. Angew. Chem., Int. Ed. 2006, 45, 5292-5296.
43. Aprahamian, I.; Olsen, J.-C.; Trabolsi, A.; Stoddart, J. F. Tetrathiafulvalene Radical Cation Dimerization in a Bistable Tripodal [4]Rotaxane. Chem. Eur. J. 2008, 14, 3889-3895.