Facile method for preparing surface-mounted cucurbit[8]uril-based rotaxanes

Langmuir

Volumn 30, Issue 36, 2014, Pages 10926-10932

  Hu, Chi ^a   Lan, Yang ^a   Tian, Feng ^a,c   West, Kevin R ^b   Scherman, Oren A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b BP EXPLORATION   (United Kingdom)

^c HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; COLLOIDS; MOLECULAR ELECTRONICS; NEUROPHYSIOLOGY;

COLLOIDAL PARTICLE; EXTERNAL STIMULUS; FUNCTIONAL SURFACES; FUNCTIONALIZED SILICA; HOST GUEST COMPLEXES; MYRIAD APPLICATIONS; REUSABLE TEMPLATES; THEORETICAL VALUES;

MOLECULES;

EID: 84921334737     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la5026125     Document Type: Article

References (38)

1. Green, J. E.; Wook Choi, J.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; De Ionno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shik Shin, Y.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. A 160-Kilobit Molecular Electronic Memory Patterned at 1011 Bits per Square Centimetre. Nature 2007, 445, 414-417.
2. Zhao, Y. L.; Dichtel, W. R.; Trabolsi, A.; Saha, S.; Aprahamian, I.; Stoddart, J. F. A Redox-Switchable α-Cyclodextrin-Based [2]Rotaxane. J. Am. Chem. Soc. 2008, 130, 11294-11296.
3. Stoddart, J. F. The Chemistry of the Mechanical Bond. Chem. Soc. Rev. 2009, 38, 1802-1820.
4. Cavallini, M.; Biscarini, F.; Leon, S.; Zerbetto, F.; Bottari, G.; Leigh, D. A. Information Storage Using Supramolecular Surface Patterns. Science 2003, 299, 531.
5. Balzani, V.; Credi, A.; Venturi, M. Molecular Machines Working on Surfaces and at Interfaces. ChemPhysChem. 2008, 9, 202-220.
6. Anslyn, E. V. Supramolecular Analytical Chemistry. J. Org. Chem. 2007, 72, 687-699.
7. Gassensmith, J.; Matthys, S.; Lee, J. J.; Wojcik, A; Kamat, P.; Smith, B. Squaraine Rotaxane as a Reversible Optical Chloride Sensor. Chem.-Eur. J. 2010, 16, 2916-2921.
8. Zhu, L. L.; Li, X.; Ji, F. Y.; Ma, X.; Wang, Q. C; Tian, H. Photolockable Ratiometric Viscosity Sensitivity of Cyclodextrin Polypseudorotaxane with Light-Active Rotor Graft. Langmuir 2009, 25, 3482-3486.
9. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit-[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 2000, 122, 540-541.
10. Rauwald, U.; Biedermann, F.; Deroo, S.; Robinson, C. V.; Scherman, O. A. Correlating Solution Binding and ESI-MS Stabilities by Incorporating Solvation Effects in a Confined Cucurbit[8]uril System. J. Phys. Chem. B 2010, 114, 8606-8615.
11. Del Barrio, J.; Horton, P. N; Lairez, D.; Lloyd, G O.; Toprakcioglu, C.; Scherman, O. A. Photocontrol over Cucurbit[8]uril Complexes: Stoichiometry and Supramolecular Polymers. J. Am. Chem. Soc. 2013, 135, 11760-11763.
12. Tian, F.; Jiao, D.; Biedermann, F.; Scherman, O. A Orthogonal Switching of a Single Supramolecular Complex. Nat. Commun. 2012, 3, 1207.
13. Tian, F.; Cheng, N; Nouvel, N; Geng, J.; Scherman, O. A Site-Selective Immobilization of Colloids on Au Substrates via a Noncovalent Supramolecular "Handcuff. Langmuir 2010, 26, 5323-5328.
14. Kim, K. Mechanically Interlocked Molecules Incorporating Cucurbituril and Their Supramolecular Assemblies. Chem. Soc. Rev. 2002, 31, 96-107.
15. Ko, Y. H.; Kim, E.; Hwang, I.; Kim, K. Supramolecular Assemblies Built with Host-Stabilized Charge-Transfer Interactions. Chem. Commun. 2007, 1305-1315.
16. Sindelar, V.; Moon, K; Kaifer, A. E. Binding Selectivity of Cucurbit[7]uril: Bis (pyridinium)-1, 4-xylylene versus 4, 4'-Bipyridinium Guest Sites. Org. Lett. 2004, 6, 2665-2668.
17. Ramalingam, V.; Urbach, A R Cucurbit[8]uril Rotaxanes. Org. Lett. 2011, 13, 4898-4901.
18. Nguyen, T. D.; Tseng, H. R; Celestre, P. C.; Flood, A. H; Liu, Y.; Stoddart, J. F.; Zink, J. I. A Reversible Molecular Valve. Proc. Natl. Acad. Sci. U. SA. 2005, 102, 10029-10034.
19. Liu, Y.; Flood, A. H; Bonvallet, 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.
20. Berna, J.; Leigh, D. A.; Lubomska, M.; Mendoza, S. M.; Perez, E. M.; Rudolf, P.; Teobaldi, G; Zerbetto, F. Macroscopic Transport by Synthetic Molecular Machines. Nat. Mater. 2005, 4, 704-710.
21. 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.
22. Zhang, X.; Wang, C. Supramolecular Amphiphiles. Chem. Soc. Rev. 2011, 40, 94-101.
23. Liu, K.; Kang, Y.; Wang, Z.; Zhang, X. 25th Anniversary Article: Reversible and Adaptive Functional Supramolecular Materials: "Noncovalent Interaction" Matters. Adv. Mater. 2013, 25, 5530-5548.
24. Jon, S. Y.; Selvapalam, N; Oh, D. H.; Kang, J.-K; Kim, S.-Y.; Jeon, Y. J.; Lee, J. W.; Kim, K Facile Synthesis of Cucurbit[n]uril Derivatives via Direct Functionalization: Expanding Utilization of Cucurbit[n]uril. J. Am. Chem. Soc. 2003, 125, 10186-10187.
25. Zhu, W.; Li, W.; Wang, C; Cui, J.; Yang, H.; Jiang, Y.; Li, G. CB[8]-Based Rotaxane as a Useful Platform for Sensitive Detection and Discrimination of Explosives. Chem. Sci. 2013, 4, 3583-3590.
26. Guo, M.; Jiang, M.; Pispas, S.; Yu, W.; Zhou, C. Supramolecular Hydrogels Made of End-Functionalized Low-Molecular-Weight PEG and α-Cyclodextrin and Their Hybridization with SiO2 Nanoparticles through Host-Guest Interaction. Macromolecules 2008, 41, 9744-9749.
27. Tian, F.; Cziferszky, M.; Jiao, D.; Wahlstrom, K; Geng, J.; Scherman, O. A. Peptide Separation through a CB[8]-Mediated Supramolecular Trap-and-Release Process. Langmuir 2011, 27, 1387-1390.
28. Lee, J. W.; Samal, S.; Selvapalam, N; Kim, H.-J.; Kim, K Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry. Acc. Chem. Res. 2003, 36, 621-630.
29. Biedermann, F.; Vendruscolo, M.; Scherman, O. A; De Simone, A.; Nau, W. M. Cucurbit[8]uril and Blue-Box: High-Energy Water Release Overwhelms Electrostatic Interactions. J. Am. Chem. Soc. 2013, 135, 14879-14888.
30. Biedermann, F.; Uzunova, V. D.; Scherman, O. A.; Nau, W. M.; De Simone, A. Release of High-Energy Water as an Essential Driving Force for the High-Affinity Binding of Cucurbit[n]urils. J. Am. Chem. Soc. 2012, 134, 15318-15323.
31. Sindelar, V.; Cejas, M. A; Raymo, F. M.; Chen, W.; Parker, S. E.; Kaifer, A. E. Supramolecular Assembly of 2, 7-Dimethyldiazapyrenium and Cucurbit[8]uril: A New Fluorescent Host for Detection of Catechol and Dopamine. Chem.-Eur. J. 2005, 11, 7054-7059.
32. Love, J. C.; Estroff, L. A.; Kriebel, J. K; Nuzzo, R G; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology. Chem. Rev. 2005, 105, 1103-1170.
33. Schreiber, F. Structure and Growth of Self-Assembling Monolayers. Prog. Surf. Sci. 2000, 65, 151-257.
34. Carta, F.; Vullo, D.; Maresca, A.; Scozzafava, A.; Supuran, C. T. Mono-/Dihydroxybenzoic Acid Esters and Phenol Pyridinium Derivatives as Inhibitors of the Mammalian Carbonic Anhydrase Isoforms I, II, VII, IX, XII and XIV. Bioorg. Med. Chem. 2013, 21, 1564-1569.
35. Zhao, Y.; Gao, Y.; Zhan, D.; Liu, H; Zhao, Q.; Kou, Y.; Shao, Y.; Li, M.; Zhuang, Q.; Zhu, Z. Selective Detection of Dopamine in the Presence of Ascorbic Acid and Uric Acid by a Carbon Nanotubes-Ionic Liquid Gel Modified Electrode. Talanta 2005, 66, 51-57.
36. Ross, C. Patterned Magnetic Recording Media. Annu. Rev. Mater. Res. 2001, 31, 203-235.
37. Lan, Y.; Wu, Y.; Karas, A.; Scherman, O. A Photoresponsive Hybrid Raspberry-Like Colloids Based on Cucurbit[8]uril Host-Guest Interactions. Angew. Chem., Int. Ed. 2014, 53, 2166-2169.
38. Barrett, C. J.; Mamiya, J.-I.; Yager, K G; Ikeda, T. Photo-Mechanical Effects in Azobenzene-Containing Soft Materials. Soft Matter 2007, 3, 1249-1261.