Taking Photochromism beyond Visible: Direct One‐Photon NIR Photoswitches Operating in the Biological Window. Issue 5 (5th January 2018)

• Record Type: Journal Article
• Authors: Klaue, Kristin; Garmshausen, Yves; Hecht, Stefan
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 5(2018)
• Page Start: 1414
• Page End: 1417
• Publication Date: 2018-01-05
• Subjects: dihydropyrenes -- near-infrared spectroscopy -- photochromism -- photopharmacology; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201709554
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The success of photopharmacology is inevitably tied to the availability of photoswitches, which can be operated within the biological window (λ=650–1450 nm) to maximize penetration in tissue. A general design strategy has been devised and a dihydropyrene derivative is described here that displays negative T‐type photochromism, allowing for efficient and nearly quantitative (95 %) switching induced by NIR light λ>800 nm. The thermal half‐life of the decolored ring‐open meta ‐cyclophanediene isomer ranges from minutes to hours, depending on the solvent polarity and hence serves as a probe of the local environment. Due to the rather subtle geometrical differences between the two isomers, suitably modified NIR photoswitches are potential candidates for switching when bound in the pocket of the biological target, in principle allowing for reversible light‐induced inhibitor deactivation as an alternative approach to externally regulate biological functions. Abstract : Leaving the visible : Donor–acceptor‐substituted dihydropyrenes can be switched almost quantitatively with light beyond λ =800 nm with control over their thermal half‐life. Both of these features are advantageous for life and material science applications.