Issue 11, 2024

Photoswitchable imines: aryliminopyrazoles quantitatively convert to long-lived Z-isomers with visible light

Abstract

Arylimines offer promise in dynamic-covalent materials due to their recyclability and ease of synthesis. However, their light-triggered E/Z isomerism has received little attention. This is attributed to challenges that include low thermal stability of their metastable state (<60 s at 20 °C), incomplete photoswitching (<50% to the metastable state), and the need for UV light (≤365 nm). We overcome these limitations with a novel class of imine photoswitch, the aryliminopyrazoles (AIPs). These AIPs can be switched using visible light (470 nm), attain photostationary states with over 95% of the Z-isomer, exhibit great resistance to fatigue, and have thermal half-lives up to 19.2 hours at room temperature. Additionally, they display T-type and negative photochromism under visible light irradiation—a useful property. The photochromic properties, quantitative assembly and accessibility of precursors set these photoswitches apart from their azo-based analogues. These findings open avenues for next-generation photoresponsive dynamic-covalent materials driven solely by these new photochromic linkages and further exploration of photocontrolled dynamic combinatorial chemistry.

Graphical abstract: Photoswitchable imines: aryliminopyrazoles quantitatively convert to long-lived Z-isomers with visible light

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Nov 2023
Accepted
14 Feb 2024
First published
14 Feb 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 3872-3878

Photoswitchable imines: aryliminopyrazoles quantitatively convert to long-lived Z-isomers with visible light

J. Wu, L. Kreimendahl, S. Tao, O. Anhalt and J. L. Greenfield, Chem. Sci., 2024, 15, 3872 DOI: 10.1039/D3SC05841G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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