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The need for ultraviolet light to induce the motion of virtually all available light-driven motors especially hampers the broad applicability of these systems. This is the fastest directional motion of a synthetic system driven by visible light to date permitting materials and biocompatible irradiation conditions to establish similarly high speeds as natural molecular motors.
They can be used to motr drive a molecular system away from equilibrium and thus represent the essential component to power future nanomachinery 8910 Since Koumura et al. However, to compete with the high efficiency and versatility of natural molecular motors 171819 considerable efforts have still to be made for synthetic systems 2021 Most light-powered molecular motors require damaging ultraviolet light to perform their task, which is a major drawback for biological or smart materials applications.
Thus, our new molecular motor system enables for the first time to power fast unidirectional rotation under ambient and non-damaging conditions, representing the next crucial step towards developing highly efficient nanomachines motor dating work at materials and biocompatible conditions. Our new molecular motor dating datig based on the hemithioindigo HTI chromophore 25an emerging photoswitch 2627282930313233 that can be operated exclusively by visible light in both switching directions.
HTI consists of a thioindigo and a stilbene fragment, which are connected via a central double bond. To confine light-induced rotations around the central double bond to one direction and exclude unwanted back-movements, we implemented additional stereochemical elements to the HTI framework: Combined with its Z and E isomeric forms, motor 1 can thus assume four different diastereomeric structures for each configuration of the stereogenic sulfur ddating, for example, Z- S - PZ- S - ME- S - M and E- S - Pwhich can be distinguished by conventional spectroscopic methods.
This molecular set-up is related to the Feringa motor system consisting motor dating a sterically overcrowded double bond in combination with carbon-based stereogenic centres 1 In our case, considerably smaller sterical hindrance between the thioindigo and stilbene fragment needed to warrant unidirectional rotation.
Results Synthesis Motor 1 was synthesized in three steps starting from known, easily accessible precursors Fig. Phenylthioacetic acid 2 ref. Because of its instability and high tendency to dimerize, benzothiophenone 3 was used in the next synthetic step in crude form. Commercially available 4,7-dimethoxyindanone 4 was methylated twice in the 2-position using sodium hydride and methyl iodide to give indanone 5. Benzothiophenone 3 was subsequently condensed with indanone 5 using boron trifluoride diethyl etherate, after dating online reviews a final oxidation with hydrogen peroxide furnished sulfoxide motor 1.
Synthesis of molecular motor 1.
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