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Expanding excitation wavelengths for azobenzene photoswitching into the near-infrared range via endothermic triplet energy transfer

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Abstract

Developing azobenzene photoswitches capable of selective and efficient photoisomerization by long-wavelength excitation is an enduring challenge. Herein, rapid isomerization from the Z- to E-state of two ortho-functionalized bistable azobenzenes with near-unity photoconversion efficiency was driven by triplet energy transfer upon red and near-infrared (up to 770 nm) excitation of porphyrin photosensitizers in catalytic micromolar concentrations. We show that the process of triplet-sensitized isomerization is efficient even when the sensitizer triplet energy is substantially lower (>200 meV) than that of the azobenzene used. This makes the approach applicable for a wide variety of sensitizer-azobenzene combinations and enables the expansion of excitation wavelengths into the near-infrared spectral range. Therefore, indirect excitation via endothermic triplet energy transfer provides efficient and precise means for photoswitching upon 770 nm near-infared light illumination with no chemical modification of the azobenzene chromophore, a desirable feature in photocontrollable biomaterials.

Graphical abstract: Expanding excitation wavelengths for azobenzene photoswitching into the near-infrared range via endothermic triplet energy transfer

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Article information


Submitted
26 Mar 2021
Accepted
25 Apr 2021
First published
27 Apr 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Advance Article
Article type
Edge Article

Expanding excitation wavelengths for azobenzene photoswitching into the near-infrared range via endothermic triplet energy transfer

J. Isokuortti, K. Kuntze, M. Virkki, Z. Ahmed, E. Vuorimaa-Laukkanen, M. A. Filatov, A. Turshatov, T. Laaksonen, A. Priimagi and N. A. Durandin, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D1SC01717A

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