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Completed
Coupling Linear and Rotary Motion: Novel Rotaxane-Rotor Hybrid Molecular Machines
FunderNetherlands Organisation for Scientific Research (NWO)
Duration01 Jun 2004 - 25 Apr 2006
Project codeS 74-60
Open Access mandatePublications: NoResearch data: No
Identifiers
Project timeline100%
Description
Coupling Linear and Rotary Motion: Novel Rotaxane-Rotor Hybrid Molecular Machines During the last decade the research into artificial molecular machines1 was intensified, since it was expected that the miniaturization of electronic components would reach their limits. Molecular machines can be defined as assemblies of molecular components which undergo mechanical-like motion as a consequence of chemical, photochemical or electrochemical stimuli Molecular rotors are defined as systems which consume energy and thereby exhibit a repetitive unidirectional rotation. One of the best defined systems has been reported by Feringa2 and is based on helical chirality. By a combination of light and thermal input, a 360 degree monodirectional rotation was accomplished. Rotaxanes are mechanically interlocked systems which consist of a dumbbell encircled by a macrocycle. Stoddart developed an extensive series of [2]rotaxanes and exploited the shuttling of the macrocycle along the linear part of the dumbbell.3 Although the conversion of rotary to linear motion is applied in almost all of our advanced mechanical machines, no molecular system with these two kinds of motion coupled is known up to now. Because it would be very challenging to prepare such a system, the first objective of this proposal is the synthesis of novel rotaxane-rotor hybrids, consisting of a rotaxane with two degenerate recognition sites and the well-defined rotor of Feringa. The coupling of the rotary and linear motion can be achieved by connecting the macrocycle of the rotaxane with a leash to the rotor. (Dynamic) NMR spectroscopical investigations on the systems with and without leash will give us information on the influence of the leash on the shuttling and rotation. The system will be optimized on the basis of the spectroscopical investigations, and ultimately the incorporation of two electronically different recognition sites are planned in order to achieve full coupling of the linear and rotary motion by electrochemical and photochemical stimuli. 1) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391. 2) N. Koumara, E. M. Geertsema, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 12005-12006. 3) A recent example: H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
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Coupling Linear and Rotary Motion: Novel Rotaxane-Rotor Hybrid Molecular Machines During the last decade the research into artificial molecular machines1 was intensified, since it was expected that the miniaturization of electronic components would reach their limits. Molecular machines can be defined as assemblies of molecular components which undergo mechanical-like motion as a consequence of chemical, photochemical or electrochemical stimuli Molecular rotors are defined as systems which consume energy and thereby exhibit a repetitive unidirectional rotation. One of the best defined systems has been reported by Feringa2 and is based on helical chirality. By a combination of light and thermal input, a 360 degree monodirectional rotation was accomplished. Rotaxanes are mechanically interlocked systems which consist of a dumbbell encircled by a macrocycle. Stoddart developed an extensive series of [2]rotaxanes and exploited the shuttling of the macrocycle along the linear part of the dumbbell.3 Although the conversion of rotary to linear motion is applied in almost all of our advanced mechanical machines, no molecular system with these two kinds of motion coupled is known up to now. Because it would be very challenging to prepare such a system, the first objective of this proposal is the synthesis of novel rotaxane-rotor hybrids, consisting of a rotaxane with two degenerate recognition sites and the well-defined rotor of Feringa. The coupling of the rotary and linear motion can be achieved by connecting the macrocycle of the rotaxane with a leash to the rotor. (Dynamic) NMR spectroscopical investigations on the systems with and without leash will give us information on the influence of the leash on the shuttling and rotation. The system will be optimized on the basis of the spectroscopical investigations, and ultimately the incorporation of two electronically different recognition sites are planned in order to achieve full coupling of the linear and rotary motion by electrochemical and photochemical stimuli. 1) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391. 2) N. Koumara, E. M. Geertsema, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 12005-12006. 3) A recent example: H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
