Orthogonal photoswitching in a multifunctional molecular system

Michael M. Lerch, Mickel J. Hansen, Willem A. Velema, Wiktor Szymanski () and Ben L. Feringa ()
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Michael M. Lerch: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen
Mickel J. Hansen: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen
Willem A. Velema: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen
Wiktor Szymanski: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen
Ben L. Feringa: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen

Nature Communications, 2016, vol. 7, issue 1, 1-10

Abstract: Abstract The wavelength-selective, reversible photocontrol over various molecular processes in parallel remains an unsolved challenge. Overlapping ultraviolet-visible spectra of frequently employed photoswitches have prevented the development of orthogonally responsive systems, analogous to those that rely on wavelength-selective cleavage of photo-removable protecting groups. Here we report the orthogonal and reversible control of two distinct types of photoswitches in one solution, that is, a donor–acceptor Stenhouse adduct (DASA) and an azobenzene. The control is achieved by using three different wavelengths of irradiation and a thermal relaxation process. The reported combination tolerates a broad variety of differently substituted photoswitches. The presented system is also extended to an intramolecular combination of photoresponsive units. A model application for an intramolecular combination of switches is presented, in which the DASA component acts as a phase-transfer tag, while the azobenzene moiety independently controls the binding to α-cyclodextrin.

Date: 2016
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DOI: 10.1038/ncomms12054

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