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Indirect Red and Near-Infrared Z-to-E Photoisomerization of ortho-Functionalized Azobenzenes via Triplet Energy Transfer

preprint
submitted on 01.03.2021, 09:25 and posted on 02.03.2021, 12:48 by Jussi Isokuortti, Kim Kuntze, Matti Virkki, Zafar Ahmed, Elina Vuorimaa-Laukkanen, Mikhail A. Filatov, Andrey Turshatov, Timo Laaksonen, Arri Priimägi, Nikita A. Durandin
Designing azobenzene photoswitches capable of selective and efficient photoisomerization by long wavelength excitation is a long-standing challenge. Indirect excitation can expand the properties of the photoswitching system beyond the intrinsic limits of azobenzenes. Herein, a rapid Z-to-E isomerization of two ortho-functionalized azobenzenes with near-unity photoconversion was facilitated via triplet energy transfer upon red and near-infrared (up to 770 nm) excitation of porphyrin photosensitizers in catalytic micromolar concentrations. Our results indicate that the whole process of triplet-sensitized isomerization is strongly entropy-driven. This ensures efficient Z-to-E photoswitching even when the azobenzene triplet energy is considerably higher (>200 meV) than for the sensitizer, which is the key for the expansion of excitation wavelengths into the near-infrared spectral range.

Funding

Academy of Finland (Grant No. 316893)

ERC Starting Grant Project PHOTOTUNE, Decision number 679646

History

Email Address of Submitting Author

jussi.isokuortti@tuni.fi

Institution

Tampere University

Country

Finland

ORCID For Submitting Author

0000-0002-4379-0087

Declaration of Conflict of Interest

No conflict of interet to declare.

Version Notes

This version is a pre-print.

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