Light‐Gated Rotation in a Molecular Motor Functionalized with a Dithienylethene Switch

Abstract

A multiphotochromic hybrid system is presented in which a light‐driven overcrowded alkene‐based molecular rotary motor is connected to a dithienylethene photoswitch. Ring closing of the dithienylethene moiety, using an irradiation wavelength different from the wavelength applied to operate the molecular motor, results in inhibition of the rotary motion as is demonstrated by detailed 1H‐NMR and UV/Vis experiments. For the first time, a light‐gated molecular motor is thus obtained. Furthermore, the excitation wavelength of the molecular motor is red‐shifted from the UV into the visible‐light region upon attachment of the dithienylethene switch.

Molecular Switches and Motors Powered by Orthogonal Stimuli

“…[58][59][60] A multiphotochromic system reported by Feringa and coworkers illustrates the interesting utility of DTE for light-gated photochromism. [61] When a DTE unit is connected to an overcrowded alkene-based rotary motor via an ethynylene linkage, 6, operation of the motor becomes dependent on the isomerization state of the DTE (Figure 7). The authors chose a DTE moiety and an overcrowded alkene that can be controlled selectively by combination of light at different wavelengths.…”

“…Light-gated photochromism of the overcrowded alkene-based rotary motor 6. [61] Although DTE and its derivatives are ubiquitous components in multiphotochromic systems, it should be noted that the degree of structural change in the switching process is miniscule. [56] A small shape change is a key aspect of the reversible photochromism of DTE in condensed phases.…”

Neue Mitglieder der National Academy of Sciences 2019

“…Feringa gehört den Redaktionsbeiräten von Advanced Synthesis & Catalysis und ChemPhotoChem sowie den internationalen Beiräten der Angewandten Chemie und des Israel Journal of Chemistry an. In der Angewandten Chemie war er zuletzt mit zwei Zuschriften über photomolekulare Motoren vertreten . Des weiteren wurde einer der Physik‐Nobelpreisträger des Jahres 2010, Konstantin S. Novoselov (National Graphene Institute, University of Manchester), in die NAS gewählt.…”

New Members and Foreign Associates of the National Academy of Sciences 2019

“…Among the newly elected foreign associates are the Nobel prize laureates of 2016 in Chemistry, Jean‐Pierre Sauvage (Université de Strasbourg, France) and Ben L. Feringa (University of Groningen, The Netherlands), who is a member of the Academic Advisory Board of Advanced Synthesis & Catalysis , the Editorial Board of ChemPhotoChem , and the International Advisory Boards of Angewandte Chemie and the Israel Journal of Chemistry . Feringa recently contributed two Communications on photomolecular motors to Angewandte Chemie . 2010 Physics Nobel laureate Konstantin S. Novoselov (National Graphene Institute, University of Manchester, UK) has also been elected foreign associate of the NAS …”