Self-assembly of functional molecular shuttles based on organic conjugated molecules

Current Organic Chemistry

Volumn 15, Issue 1, 2011, Pages 96-107

  Li, Yongjun ^a   Liu, Huibiao ^a   Li, Yuliang ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Energy transfer; Fluorescence switch; Molecular machine; Molecular transporting; Nanostructure; Self assembly

Indexed keywords

ENERGY TRANSFER; FLUORESCENCE; MOLECULES; SYNTHESIS (CHEMICAL);

CONJUGATED MOLECULES; ENERGY-TRANSFER; FLUORESCENCE SWITCH; MOLECULAR CONSTRUCTION; MOLECULAR DESIGN; MOLECULAR MACHINES; MOLECULAR SHUTTLE; MOLECULAR SYNTHESIS; MOLECULAR TRANSPORTING; ORGANICS;

SELF ASSEMBLY;

EID: 78951495882     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211793797792     Document Type: Article

References (83)

1. Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart J. F. Artificial molecular machines. Angew. Chem. Int. Ed., 2000, 39, 3349-3391.
2. Molecular devices and machines: a journey into the nano world. Balzani, V.; Credi, A.; Venturi, M. Eds.; Wiley-VCH, Weinheim, 2003.
3. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed., 2007, 46, 72-191.
4. Bissell, R. A.; Cordova, E.; Kaifer, A. E.; Stoddart, J. F. A Chemically and electrochemically switchable molecular shuttle. Nature, 1994, 369, 131-137.
5. 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. USA, 2005, 102, 10029-10034.
6. Badjic, J. D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F. A molecular elevator. Science, 2004, 303, 1845-1849.
7. Collin, J. P.; Dietrich-Buchecker, C.; Gaviña, P.; Jimenez-molero, M. C.; Sauvage, J.-P. Shuttles and muscles: Linear molecular machines based on transition metals. Acc. Chem. Res., 2001, 34, 477-487.
8. Lane, A. S.; Leigh, D. A.; Murphy, A. Peptide-based molecular shuttles. J. Am. Chem. Soc., 1997, 119, 11092-11093.
9. Chatterjee, M. N.; Kay, E. R.; Leigh, D. A. Beyond switches: Ratcheting a particle energetically uphill with a compartmentalized molecular machine. J. Am. Chem. Soc., 2006, 128, 4058-4073.
10. Leigh, D. A.; Wong, J. K. Y.; Dehez, F.; Zerbetto, F. Unidirectional rotation in a mechanically interlocked molecular rotor. Nature, 2003, 424, 174-179.
11. Hernandez, V.; Kay, E. R.; Leigh, D. A. A reversible synthetic rotary molecular motor. Science, 2004, 306, 1532-1537.
12. Kihara, N.; Hashimoto, M.; Takata, T. Redox behavior of ferrocene-containing rotaxane: Transposition of the rotaxane wheel by redox reaction of a ferrocene moiety tethered at the end of the axle. Org. Lett., 2004, 6, 1693-1696.
13. Mateo-Alonso, A.; Ehli, C.; Aminur Rahman, G. M.; Guldi, D. M.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Prato, M. Tuning electron transfer through translational motion in molecular shuttles. Angew. Chem. Int. Ed., 2007, 46, 3521.
14. Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Whence molecular electronics. Science, 2004, 306, 2055-2056.
15. Bottari, G.; Leigh, D. A.; Perez, E. M. Chiroptical switching in a bistable molecular shuttle. J. Am. Chem. Soc., 2003, 125, 13360-13361.
16. Perez, E. M.; Dryden, D. T. F.; Leigh, D. A.; Teobaldi, G.; Zerbetto, F. A generic basis for some simple light-operated mechanical molecular machines. J. Am. Chem. Soc., 2004, 126, 12210-12211.
17. Wang, Q.-C.; Qu, D.-H.; Ren, J.; Chen, K.; Tian, H. A lockable light-driven molecular shuttle with a fluorescent signal. Angew. Chem. Int. Ed., 2004, 43, 2661-2665.
18. Davis A. P. Nanotechnology - Synthetic molecular motors. Nature, 1999, 401, 120-121.
19. Vicario, J.; Walko, M.; Meetsma, A.; Feringa, B. L. Fine tuning of the rotary motion by structural modification in light-driven unidirectional molecular motors. J. Am. Chem. Soc., 2006, 128, 5127-5135.
20. Dahl, J.; Branchaud, B. P. 180 degrees unidirectional bond rotation in a biaryl lactone artificial molecular motor prototype. Org. Lett., 2006, 8, 5841-5844.
21. Saha, S.; Flood, A. H.; Stoddart, J. F.; Impellizzeri, S.; Silvi, S.; Venturi, M.; Credi, A. A redox-driven multicomponent molecular shuttle. J. Am. Chem. Soc., 2007, 129, 12159-12171.
22. Leigh, D. A.; Thomson, A. R. Switchable dual binding mode molecular shuttle. Org. Lett., 2006, 8, 5377-5379.
23. Qu, D.-H.; Wang, Q.-C.; Ma, X.; Tian, H. A. [3]Rotaxane with three stable states that responds to multiple-inputs and displays dual fluorescence addresses. Chem. Eur. J., 2005, 11, 5929-5937.
24. Jimenez-Molero, M. C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Towards artificial muscles at the nanometric level. Chem. Commun., 2003, 1613-1616.
25. Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, T. J.; Huang, B.; Brough, M.; Baller, S.; Magonov, S. D.; Solares, W. A.; Goddard, C.-M.; Ho, J. O.; Stoddart, J. F. Linear artificial molecular muscles. J. Am. Chem. Soc., 2005, 127, 9745-9759.
26. Huang, T. J.; Brough, B.; Ho, C.-M.; Liu, Y.; Flood, A. H.; Bonvallet, P.; Tseng, H.-R.; Stoddart, J. F.; Baller, M.; Magonov, S. A nanomechanical device based on linear molecular motors. Appl. Phys. Lett., 2004, 85, 5391-5393.
27. Sherman, B.; Seeman, N. C. A precisely controlled DNA biped walking device. Nano. Lett., 2004, 4, 1203-1207.
28. Shin, J.S.; Pierce, N. A. A synthetic DNA walker for molecular transport. J. Am. Chem. Soc., 2004, 126, 10834-10835.
29. Badjic, J. D.; Ronconi, C. M.; Stoddart, J. F.; Balzani, V.; Silvi, S.; Credi, A. Operating molecular elevators. J. Am. Chem. Soc., 2006, 128, 1489-1499.
30. Leigh, D. A. Macroscopic transport by synthetic molecular machines. Nat. Mater., 2005, 4, 704-710.
31. Wan, P. B.; Jiang, Y. G.; Wang, Y. P.; Wang, Z. Q.; Zhang, X. Tuning surface wettability through photocontrolled reversible molecular shuttle. Chem. Commun., 2008, 5710-5172.
32. Yau, C. M. S.; Pascu, S. I.; Odom, S. A.; Warren, J. E.; Klotz, E. J. F.; Frampton, M. J.; Williams, C. C.; Coropceanu, V.; Kuimov, M. K.; Phillips, D.; Barlow, S.; Brédas, J.-L.; Marder, S. R.; Millarf, V.; Anderson, H. L. Stabilisation of a heptamethine cyanine dye by rotaxane encapsulation. Chem. Commun., 2008, 2897-2899.
33. Arunkumar, E.; Forbes, C. C.; Noll, B. C.; Smith, B. D. Squaraine-derived rotaxanes: Sterically protected fluorescent near-IR dyes. J. Am. Chem. Soc., 2005, 127, 3288-3289.
34. Johnson, J. R.; Fu, N.; Arunkumar, E.; Leevy, W. M.; Gammon, S. T.; Piwnica-Worms, D.; Smith, B. D. Squaraine rotaxanes: Superior substitutes for Cy-5 in molecular probes for near-infrared fluorescence cell imaging. Angew. Chem., Int. Ed., 2007, 46, 5528-5531.
35. Hsueh, S.-Y.; Lai, C.-C.; Liu, Y.-H.; Wang, Y.; Peng, S.-M.; Chiu, S.-H. Protecting a squaraine near-IR dye through its incorporation in a slippage-derived [2]Rotaxane. Org. Lett., 2007, 9, 4523-4526.
36. Frampton, M. J.; Sforazzini, G.; Brovelli, S.; Latini, G.; Townsend, E.; Williams, C. C.; Charas, A.; Zalewski, L.; Kaka, N. S.; Sirish, M.; Parrott, L. J.; Wilson, J. S.; Cacialli, F.; Anderson, H. L. Synthesis and optoelectronic properties of nonpolar polyrotaxane insulated molecular wires with high solubility in organic solvents. Adv. Funct. Mater., 2008, 18, 3367-3376.
37. Mateo-Alonso, A.; Ehli, C.; Guldi, D. M.; Prato, M. Charge transfer reactions along a supramolecular redox gradient. J. Am. Chem. Soc., 2008, 130, 14938.
38. Kaletasü, K.; Dobrawa, R.; Sautter, A.; Würthner, F.; Zimine, M.; De Cola, L.; William, R. M. Photoinduced electron and energy transfer processes in a bichromophoric pyrene-perylene bisimide system. J. Phys. Chem. A, 2004, 108, 1900-1909.
39. Förster, T. Zwischienmolekular energiewanderung und fluoreszenz. Ann. Phys., 1948, 2,55-75.
40. Li, Y.J.; Li, H.; Li, Y. L.; Liu, H. B.; Wang, S.; He, X. R.; Wang, N.; Zhu, D. B. Energy transfer switching in a bistable molecular machine. Org. Lett., 2005, 7, 4835-4838.
41. Wang, J.-Y.; Han, J.-M.; Yan, J.; Ma, Y.G.; Pei, J. A mechanically inter-locked [3]Rotaxane as a light-harvesting antenna: synthesis, characterization, and intramolecular energy transfer. Chem. Eur. J., 2009, 15, 3585-3594.
42. Katz, E.; Sheeney-Haj-Ichia, L.; Willner, I. Electrical contacting of glucose oxidase in a redox-active rotaxane configuration. Angew. Chem., Int. Ed., 2004, 43, 3292-3300.
43. MartSnez-DSaz, M.-V.; Spencer, N.; Stoddart, J. F. The self-assembly of a switchable [2]rotaxane. Angew. Chem. Int. Ed., 1997, 36, 1904-1907.
44. Li, J. B.; Li, Y. J.; Guo, Y. B.; Xu, J. L.; Lv, J.; Li, Y. L.; Liu, H. B.; Wang, S. A Novel Supramolecular System: Combination of Two Switchable Processes in a [2]Rotaxane. Chem. Asian. J., 2008, 3, 2091-2096.
45. Arnaud-Neu, F.; Collins, E. M.; Deasy, M.; Ferguson, G.; Harris, S. J.; Kaitner, B.; Lough, A. J.; McKervey, M. A.; Marques, E.; Ruhl, B. L.; Schwing-Weill, M. J.; Seward, E. M. Synthesis, X-ray crystal-structures, and cation-binding properties of alkyl calixaryl esters and ketones, a new family of macrocyclic molecular receptors. J. Am. Chem. Soc., 1989, 111, 8681-8691.
46. -1, see Gokel, G. W.; Leevy, W. M.; Weber, M. E. Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev., 2004, 104, 2723-2750.
47. Wang, X. Y.; Bao, X. F.; McFarland-Mancini, M.; Isaacsohn, I.; Drew, A. F.; Smithrud, D. B. Investigation of the intracellular delivery of fluoresceinated peptides by a host-[2]rotaxane. J. Am. Chem. Soc., 2007, 129, 7284-7293.
48. Frey, J.; Tock, C.; Collin, J. P.; Heitz, V.; Sauvage, J. P. A [3]rotaxane with two porphyrinic plates acting as an adaptable receptor. J. Am. Chem. Soc., 2008, 130, 4592-4593.
49. Marois, J.-S.; Cantin, K.; Desmarais, A.; Morin, J.-F. [3]rotaxane-porphyrin conjugate as a novel supramolecular host for fullerenes. Org. Lett., 2008, 10, 33-36.
50. Brown, A.; Mullen, K. M.; Ryu, J.; Chmielewski, M. J.; Santos, S. M.; Felix, V.; Thompson, A. L.; Warren, J. E.; Pascu, S. I.; Beer, P. D. Interlocked Host Anion Recognition by an Indolocarbazole-Containing [2]Rotaxane. J. Am. Chem. Soc., 2009, 131, 4937-4952.
51. Mullen, K. M.; Mercurio, J.; Serpell, C. J.; Beer, P. D. Exploiting the 1,2,3-Triazolium Motif in Anion-Templated Formation of a Bromide-Selective Rotaxane Host Assembly. Angew. Chem. Int. Ed., 2009, 48, 4781-4784.
52. Kramer, P.; Weber, W.; Fussenegger, M. Artificial regulatory networks and cascades for discrete multilevel transgene control in mammalian cells. Biotechnol. Bioeng., 2003, 83, 810-820.
53. Zhou, W. D.; Li, J. B.; He, X. R.; Li, C. H.; Lv, J.; Li, Y. L.; Wang, S.; Liu, H. B.; Zhu, D. B. A Molecular Shuttle for Driving a Multilevel Fluorescence Switch. Chem. Eur. J., 2008, 14, 754-763.
54. Kwan, P. H.; Swager, T. M. Intramolecular photoinduced charge transfer in rotaxanes. J. Am. Chem. Soc., 2005, 127, 5902-5909.
55. Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J. K. M.; Stoddart, J. F. Switchable neutral bistable rotaxanes. J. Am. Chem. Soc., 2004, 126, 9884-9885.
56. de Silva, A. P.; Dixon, I. M.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Maxwell, P. R. S.; Rice, T. E. Integration of logic functions and sequential operation of gates at the molecular-scale. J. Am. Chem. Soc., 1999, 121, 1393-1394.
57. Magri, D.C.; Brown, G. J.; McClean, G. D.; de Silva, A. P. Communicating chemical congregation: A molecular AND logic gate with three chemical inputs as a lab-on-a-molecule prototype. J. Am. Chem. Soc., 2006, 128, 4950-4951.
58. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev., 1997, 97, 1515-1566.
59. Leigh, D. A.; Morales, M. A. F.; Perez, E. M.; Wong, J. K. Y.; Saiz, C. G.; Slawin, A. M. Z.; Carmichael, A. J.; Haddleton, D. M.; Brouwer, A. M.; Buma, W. J.; Wurpel, G. W. H.; Leon, S.; Zerbetto, F. Patterning through controlled submolecular motion: Rotaxane-based switches and logic gates that function in solution and polymer films. Angew. Chem. Int. Ed., 2005, 44, 3062-3067.
60. Raymo, M.; Alvarado, R. J.; Giordani, S.; Cejas, M. A. Memory effects based on intermolecular photoinduced proton transfer. J. Am. Chem. Soc., 2003, 125, 2361-2364.
61. Guo, X. F.; Zhang, D. Q.; Zhang, G. X.; Zhu, D.B. Monomolecular logic: Half-adder based on multistate/multifunctional photochromic spiropyrans. J. Phys. Chem. B., 2004, 108, 11942-11945.
62. Keaveney, C. M.; Leigh, D. A. Shuttling through anion recognition. Angew. Chem., Int. Ed., 2004, 43, 1222-1224.
63. Zhou, W. D.; Chen, D. G.; Li, J. B.; Xu, J. L.; Lv, J.; Liu, H. B.; Li, Y. L. Photoisomerization of Spiropyran for Driving a Molecular Shuttle. Org. Lett., 2007, 9, 3929-3932.
64. Leigh, D.A.; Murphy, A.; Smart, J. P.; Slawin, A. M. Z. Glycylglycine rotaxanes - The hydrogen bond directed assembly of synthetic peptide rotaxanes. Angew. Chem., Int. Ed., 1997, 36, 728-732.
65. Supramolecular chemistry, concepts and perspectives. Lehn, J.-M. Eds.; Wiley VCH, Weinheim, Germany, 1995.
66. Hoeben, J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. About supramolecular assemblies of pi-conjugated systems. Chem. Rev., 2005, 105, 1491-1546.
67. Gan, H. Y.; Liu, H. B.; Li, Y. J.; Zhao, Q.; Li, Y. L.; Wang, S.; Jiu, T. G.; Wang, N.; He, X. R.; Yu, D. P.; Zhu, D. B. Fabrication of polydiacetylene nanowires by associated self-polymerization and self-assembly processes for efficient field emission properties. J. Am. Chem. Soc., 2005, 127, 12452-12453.
68. Jeukens, R. L. P. N.; Jonkheijm, P.; Wijnen, F. J. P.; Gielen, J. C.; Christianen, P. C. M.; Schenning, A. P. H. J.; Meijer, E. W.; Maan, J. C. Polarized emission of individual self-assembled oligo(p-phenylenevinylene)-based nanofibers on a solid support. J. Am. Chem. Soc., 2005, 127, 8280-8281.
69. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J.; Zang, L. Nanobelt self-assembly from an organic n-type semiconductor: Propoxyethyl-PTCDI. J. Am. Chem. Soc., 2005, 127, 10496-10497.
70. Li, Y. J.; Li, X. F.; Li, Y. L.; Liu, H. B.; Wang, S.; Gan, H. Y.; Li, J. B.; Wang, N.; He, X. R.; Zhu, D. B. Amphiphilic Bis-porphyrin-Bipyridinium-Palladium Complex: From Multibilayer Vesicles to Hollow Capsules. Angew. Chem., Int. Ed., 2006, 45, 3639-3643.
71. Würthner, F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem. Commun., 2004, 1564-1579.
72. Li, Y. J.; Zheng, H. Y.; Li, Y. L.; Wang, S.; Liu, H. B.; Jiang, L.; Zhu, D. B. Synthesis, Characterization, and Self-Assembly of Nitrogen-Containing Heterocoronenetetracarboxylic Acid Diimide Analogues: Photocyclization of N-Heterocycle-Substituted Perylene Bisimides. Chem. Eur. J., 2006, 12, 8378-8385.
73. Wu, D.; Zhi, L.; Bodwell, G. J.; Cui, G.; Tsao, N.; Müllen, K. Self-assembly of positively charged discotic PAHs: From nanofibers to nanotubes. Angew. Chem., Int. Ed., 2007, 46, 5417-5420.
74. Zhou, W. D.; Xu, J. L.; Zheng, H. Y.; Liu, H. B.; Li, Y. L.; Zhu, D. B. Charge Transfer Chromophore-Stopped [2]Rotaxane through [2 + 2] Cycloaddition. J. Org. Chem., 2008, 73, 7702-7709.
75. Zhou, W. D.; Xu, J. L.; Zheng, H. Y.; Yin, X. D.; Zuo, Z. C.; Liu, H. B.; Li, Y. L. Distinct nanostructures from a molecular shuttle: effects of shuttling movement on nanostructural morphologies. Adv. Funct. Mater., 2009, 19, 141-149.
76. Xu, J. L.; Liu, X. F.; Lv, J.; Zhu, M.; Huang, C. S.; Zhou, W. D.; Yin, X. D.; Liu, H. B.; Li, Y. L.; Ye, J. P. Morphology Transition and Aggregation-Induced Emission of an Intramolecular Charge-Transfer Compound. Langmuir, 2008, 24, 4231-4237.
77. Zhou, S.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Spherical bilayer vesicles of fullerene-based surfactants in water: A laser light scattering study. Science, 2001, 291, 1944-1947.
78. Vriezema, D. M.; Hoogboom, J.; Velonia, K.; Takazawa, K.; Christianen, P. C. M.; Maan, J. C.; Rowan, A. E.; Nolte, R. J. M. Vesicles and polymerized vesicles from thiophene-containing rod-coil block copolymers. Angew. Chem., Int. Ed., 2003, 42, 772-776.
79. Michinobu, T.; May, J. C.; Lim, J. H.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Biaggio, I.; Diederich, F. A new class of organic donor-acceptor molecules with large third-order optical nonlinearities. Chem. Commun., 2005, 737-739.
80. Michinobu, T.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Frank, B.; Moonen, N. N. P.; Gross, M.; Diederich, F. Donor-substituted 1,1,4,4-tetracyanobutadienes (TCBDs): New chromophores with efficient intramolecular charge-transfer interactions by atom-economic synthesis. Chem. Eur. J., 2006, 12, 1889-1905.
81. Jeon, Y. J.; Bharadwaj, P. K.; Choi, S. W.; Lee, J. W.; Kim, K. Supramolecular amphiphiles: Spontaneous formation of vesicles triggered by formation of a charge-transfer complex in a host. Angew. Chem., Int. Ed., 2002, 41, 4474-4476.
82. 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.
83. Zhao, Y.-L.; Aprahamian, I.; Trabolsi, A.; Erina, N.; Stoddart, J. F. Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor. J. Am. Chem. Soc., 2008, 130, 6348-6350.