Diaryltriazolium Photoswitch: Reaching a Millisecond Cycloreversion with High Stability and NIR Absorption

Angewandte Chemie, vol. 136

Abstract

Abstract The exceptional thermal stability of diarylethene closed isomers enabled many applications but also prevented utilization in photochromic systems that require rapid thermal reversibility. Herein, we report the diaryltriazolium (DAT+) photoswitch undergoing thermal cycloreversion within a few milliseconds and absorption of the closed form in the near‐infrared region above 900 nm. Click chemistry followed by alkylation offers modular and fast access to the electron‐deficient DAT+ scaffold. In addition to excellent fatigue resistance, the introduced charge increases water solubility, rendering this photoswitch an ideal candidate for exploring biological applications.

Authors 5

1. Dušan Kolarski Aachen

   DWI – Leibniz Institute for Interactive Materials · Max Planck Institute for Multidisciplinary Sciences

   Affiliation as printed

   DWI-Leibniz Institute for Interactive Materials Forckenbeckstr. 50 52074 Aachen Germany

   Max Planck Institute for Multidisciplinary Sciences, NanoBioPhotonics Am Faßberg 11 37077 Göttingen Germany

   DWI-Leibniz Institute for Interactive Materials Forckenbeckstr. 50 52074 Aachen Germany

2. Pit Steinbach Aachen Institute of Physical Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Physical Chemistry RWTH Aachen University Melatener Str. 20 52074 Aachen Germany

   Institute of Physical Chemistry RWTH Aachen University Melatener Str. 20 52074 Aachen Germany

3. Christoph Bannwarth Aachen Institute of Physical Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Physical Chemistry RWTH Aachen University Melatener Str. 20 52074 Aachen Germany

   Institute of Physical Chemistry RWTH Aachen University Melatener Str. 20 52074 Aachen Germany

4. Kristin Klaue

   Humboldt-Universität zu Berlin

   Affiliation as printed

   Center for the Science of Materials Berlin Humboldt-Universität zu Berlin Zum Großen Windkanal 2 12489 Berlin Germany

   Department of Chemistry Humboldt-Universität zu Berlin Brook-Taylor-Str. 2 12489 Berlin Germany

   Department of Chemistry Humboldt-Universität zu Berlin Brook-Taylor-Str. 2 12489 Berlin Germany

5. Stefan Hecht corresponding Aachen Institute of Technical and Macromolecular Chemistry

   Humboldt-Universität zu Berlin · DWI – Leibniz Institute for Interactive Materials · RWTH Aachen University

   Affiliation as printed

   Center for the Science of Materials Berlin Humboldt-Universität zu Berlin Zum Großen Windkanal 2 12489 Berlin Germany

   DWI-Leibniz Institute for Interactive Materials Forckenbeckstr. 50 52074 Aachen Germany

   Department of Chemistry Humboldt-Universität zu Berlin Brook-Taylor-Str. 2 12489 Berlin Germany

   Institute of Technical and Macromolecular Chemistry RWTH Aachen University Forckenbeckstraße 52074 Aachen Germany