A molecular shuttle that operates inside a metal-organic framework

Nature Chemistry

Volumn 7, Issue 6, 2015, Pages 514-519

  Zhu, Kelong ^a   O'Keefe, Christopher A ^a   Vukotic, V Nicholas ^a   Schurko, Robert W ^a   Loeb, Stephen J ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84930212620     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2258     Document Type: Article

References (47)

1. Anelli, P. L., Spencer, N. & Stoddart, J. F. A molecular shuttle. J. Am. Chem. Soc. 113, 5131-5133 (1991).
2. Sauvage, J-P. & Dietrich-Buchecker, C. (eds) Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology (Wiley-VCH, 1999).
3. Thordarson, P., Bijsterveld, E. J. A., Rowan, A. E. & Nolte, R. J. M. Epoxidation of polybutadiene by a topologically linked catalyst. Nature 424, 915-918 (2003).
4. Kay, E. K., Leigh, D. A. & Zerbetto, F. Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed. 46, 72-191 (2007).
5. Gong, H-Y., Rambo, B. M., Karnas, E., Lynch, V. M. & Sessler, J. L. A 'Texas-sized' molecular box that forms an anion-induced supramolecular necklace. Nature Chem. 2, 406-409 (2010).
6. Lee, S., Chen, C-H. & Flood, A. H. A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3] rotaxanes. Nature Chem. 5, 704-710 (2013).
7. Langton, M. J. & Beer, P. D. Rotaxane and catenane host structures for sensing charged guest species. Acc. Chem. Res. 47, 1935-1949 (2014).
8. Stoddart, J. F. Putting mechanically interlocked molecules (MIMs) to work in tomorrow's world. Angew. Chem. Int. Ed. 53, 11102-11104 (2014).
9. Bissell, R. A., Córdova, E., Kaifer, A. E. & Stoddart, J. F. A chemically and electrochemically switchable molecular shuttle. Nature 369, 133-137 (1994).
10. Marlin, D. S., Cabrera, D. G., Leigh, D. A. & Slawin, A. M. Z. An allosterically regulated molecular shuttle. Angew. Chem. Int. Ed. 45, 1385-1390 (2006).
11. Bottari, G., Leigh, D. A. & Pérez, E. M. Chiroptical switching in a bistable molecular shuttle. J. Am. Chem. Soc. 125, 13360-13361 (2003).
12. Vella, S. J., Tiburcio, J. & Loeb, S. J. Optically sensed molecular shuttles driven by acid-base chemistry. Chem. Commun. 4752-4754 (2007).
13. Berná, J. et al. Macroscopic transport by synthetic molecular machines. Nature Mater. 4, 704-710 (2005).
14. Feringa, B. L. & Browne, W. R. (eds) Molecular Switches 2nd edn (Wiley-VCH, 2011).
15. Collier, C. P. et al. A [2]catenane-based solid-state electronically reconfigurable switch. Science 289, 1172-1175 (2000).
16. Fahrenbach, A. C. et al. Organic switches for surfaces and devices. Adv. Mater. 25, 331-348 (2013).
17. Lewandowski, B. et al. Sequence-specific peptide synthesis by an artificial small-molecule machine. Science 339, 189-193 (2013).
18. Li, H. et al. Relative unidirectional translation in an artificial molecular assembly fueled by light. J. Am. Chem. Soc. 135, 18609-18620 (2013).
19. Ragazzon, G., Baroncini, M., Silvi, S., Venturi, M. & Credi, A. Light-powered autonomous and directional molecular motion of a dissipative self-assembling system. Nature Nanotech. 10, 70-75 (2015).
20. Coskun, A., Banaszak, M., Astumian, R. D., Stoddart, J. F. & Grzybowski, B. A. Great expectations: can artificial molecular machines deliver on their promises? Chem. Soc. Rev. 41, 19-31 (2012).
21. Balzani, V., Credi, A. & Venturi, M. Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld (Wiley InterScience, 2008).
22. Balzani, V. Nanoscience and nanotechnology: the bottom-up construction of molecular devices and machines. Pure Appl. Chem. 80, 1631-1650 (2008).
23. Deng, H. X., Olson, M. A., Stoddart, J. F. & Yaghi, O. M. Robust dynamics. Nature Chem. 2, 439-443 (2010).
24. Zhou, H-C, Long, J. R. & Yaghi, O. M. Introduction to metal-organic frameworks. Chem. Rev. 112, 673-674 (2012).
25. Li, H., Eddaoudi, M., O'Keeffe, M. & Yaghi, O. M. Design and synthesis of an exceptionally stable and highly porous metal-organic framework. Nature 402, 276-279 (1999).
26. Furukawa, H., Cordova, K. E., O'Keeffe, M. & Yaghi, O. M. The chemistry and applications of metal-organic frameworks. Science 341, 1230444 (2013).
27. Lu, W. et al. Tuning the structure and function of metal-organic frameworks via linker design. Chem. Soc. Rev. 43, 5561-5593 (2014).
28. Li, Q. et al. Docking in metal-organic frameworks. Science 325, 855-859 (2009).
29. Li, Q. et al. A catenated strut in a catenated metal-organic framework. Angew. Chem. Int. Ed. 49, 6751-6755 (2010).
30. Li, Q. et al. A metal-organic framework replete with ordered donor-acceptor catenanes. Chem. Commun. 380-382 (2010).
31. Coskun, A. et al. Metal-organic frameworks incorporating copper-complexed rotaxanes. Angew. Chem. Int. Ed. 51, 2160-2163 (2012).
32. Cao, D. et al. Three-dimensional architectures incorporating stereoregular donor-acceptor stacks. Chem. Eur. J. 19, 8457-8465 (2013).
33. Strutt, N. L. et al. Incorporation of an A1/A2-difunctionalized pillar[5]arene into a metal-organic framework. J. Am. Chem. Soc. 134, 17436-17439 (2012).
34. Vukotic, V. N. & Loeb, S. J. Coordination polymers containing rotaxanes as linkers. Chem. Soc. Rev. 41, 5896-5906 (2012).
35. Loeb, S. J. Rotaxanes as ligands: from molecules to materials. Chem. Soc. Rev. 36, 226-235 (2007).
36. Vukotic, V. N., Harris, K. J., Zhu, K., Schurko, R. W. & Loeb, S. J. Metal-organic frameworks with dynamic interlocked components. Nature Chem. 4, 456-460 (2012).
37. Zhu, K., Vukotic, V N., O'Keefe, C. A., Schurko, R. W. & Loeb, S. J. Metal-organic frameworks with mechanically interlocked pillars: controlling ring dynamics in the solid-state via a reversible phase change. J. Am. Chem. Soc. 136, 7403-7409 (2014).
38. Eddaoudi, M. et al. Systematic design of pore size and functionality in isoreticular MOFs and their application in methane storage. Science 295, 469-472 (2002).
39. Oisaki, K., Li, Q., Furukawa, H., Czaja, A. U. & Yaghi, O. M. A metal-organic framework with covalently bound organometallic complexes. J. Am. Chem. Soc. 132, 9262-9264 (2010).
40. Zhu, K., Vukotic, V. N. & Loeb, S. J. Molecular shuttling of a compact and rigid, H-shaped [2]rotaxane. Angew. Chem Int. Ed. 51, 2168-2172 (2012).
41. Zhu, K., Vukotic, V N., Noujeim, N. & Loeb, S. J. Bis(benzimidazolium) axles and crown ether wheels: a versatile templating pair for the formation of [2]rotaxane molecular shuttles. Chem. Sci. 3, 3265-3271 (2012).
42. Vandersluis, P. & Spek, A. L. Bypass-an effective method for the refinement of crystal-structures containing disordered solvent regions. Acta Crystallogr. A46, 194-201 (1990).
43. Noujeim, N., Zhu, K., Vukotic, V. N. & Loeb, S. J. [2]Pseudorotaxanes from T-shaped benzimidazolium axles and [24]crown-8 wheels. Org. Lett. 14, 2484-2487 (2012).
44. Bain, A. D. Chemical exchange in NMR. Prog. Nucl. Magn. Reson. Spectrosc. 43, 63-103 (2003).
45. Karlen, S. D. et al. Symmetry and dynamics of molecular rotors in amphidynamic molecular crystals. Proc. Natl Acad. Sci. USA 107, 14973-14977 (2010).
46. Jeener, J., Meier, B. H., Bachmann, P. & Ernst, R. R. Investigation of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 71, 4546-4553 (1979).
47. Perrin, C. L. & Dwyer, T. J. Application of two-dimensional NMR to kinetics of chemical exchange. Chem. Rev. 90, 935-967 (1990).