Abstract
This update reviews the major developments on rotaxane-based shuttles during the period of August 2008 to October 2010 and is organized similarly to the previous review [1].
The progress in the field of chemical controlled shuttles can be summarized as a significant increase of the shuttling rates, second-generation pH-switchable Pd(II)-complexed rotaxanes, and new synthetic approaches, especially those based on Diels-Alder cycloadditions. The new synthetic routes allow ready access to rotaxanes that feature the template site fully incorporated into the interlocked product. This template site is unusual for active-template reactions and produces shuttles that exhibit entropy-driven translational isomerism with remarkably improved positional discrimination as was shown by the incorporation of a hydrogen-bonding TEG-station into an imine-bridged rotaxane.
With respect to photochemically powered molecular switches, the most important result originated from the synthesis of a degenerate, donor-acceptor, light-gated, STOP-GO molecular shuttle. For electrochemically controllable bistable rotaxanes, the first example of a molecular shuttle with three different stations, which dramatically increase the shuttling process rate, has been reported.
Finally, the last study in this review involves redox-driven switching and electrochromic responses of LC films containing a bistable [2]rotaxane. The presence of a polymer electrolyte provides new prospects for the further development of rotaxane-based molecular materials by exploiting the dynamic, anisotropic, and coherent properties of liquid crystals.
Keywords: Mechanically interlocked molecules, Click chemistry, Molecular devices, Nanoscale machines, Rotaxane-Based, Shuttles, interlocked machines, chemically, photochemically, electrochemically, induced molecular, ring component, molecules, synthetic methodologies, kinetics
Current Organic Chemistry
Title: Recent Developments on Rotaxane-Based Shuttles: An Update to 2010
Volume: 16 Issue: 2
Author(s): Antonio Rescifina, Ugo Chiacchio, Antonino Corsaro and Giovanni Romeo
Affiliation:
Keywords: Mechanically interlocked molecules, Click chemistry, Molecular devices, Nanoscale machines, Rotaxane-Based, Shuttles, interlocked machines, chemically, photochemically, electrochemically, induced molecular, ring component, molecules, synthetic methodologies, kinetics
Abstract: This update reviews the major developments on rotaxane-based shuttles during the period of August 2008 to October 2010 and is organized similarly to the previous review [1].
The progress in the field of chemical controlled shuttles can be summarized as a significant increase of the shuttling rates, second-generation pH-switchable Pd(II)-complexed rotaxanes, and new synthetic approaches, especially those based on Diels-Alder cycloadditions. The new synthetic routes allow ready access to rotaxanes that feature the template site fully incorporated into the interlocked product. This template site is unusual for active-template reactions and produces shuttles that exhibit entropy-driven translational isomerism with remarkably improved positional discrimination as was shown by the incorporation of a hydrogen-bonding TEG-station into an imine-bridged rotaxane.
With respect to photochemically powered molecular switches, the most important result originated from the synthesis of a degenerate, donor-acceptor, light-gated, STOP-GO molecular shuttle. For electrochemically controllable bistable rotaxanes, the first example of a molecular shuttle with three different stations, which dramatically increase the shuttling process rate, has been reported.
Finally, the last study in this review involves redox-driven switching and electrochromic responses of LC films containing a bistable [2]rotaxane. The presence of a polymer electrolyte provides new prospects for the further development of rotaxane-based molecular materials by exploiting the dynamic, anisotropic, and coherent properties of liquid crystals.
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Cite this article as:
Rescifina Antonio, Chiacchio Ugo, Corsaro Antonino and Romeo Giovanni, Recent Developments on Rotaxane-Based Shuttles: An Update to 2010, Current Organic Chemistry 2012; 16 (2) . https://dx.doi.org/10.2174/138527212798993040
DOI https://dx.doi.org/10.2174/138527212798993040 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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