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

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. Diaryltriazolium photoswitch (DAT+) was prepared by alkyne-azide cycloaddition followed by alkylation. Due to a charged heterocyclic bridge, the closed isomer of DAT+ exhibits the most bathochromically shifted absorption maximum and the shortest thermal half-life reported for any diarylethene thus far. The new photoswitch exhibits excellent fatigue resistance and is well water-soluble.image