Triplet-Triplet Energy Transfer: A Simple Strategy for an Efficient Visible Light-Induced Photoclick Reaction

Youxin Fu, Georgios Alachouzos, Nadja A Simeth, Mariangela Di Donato, Michiel F Hilbers, Wybren Jan Buma, Wiktor Szymanski*, Ben L Feringa*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

Samenvatting

Photoclick reactions combine the advantages offered by light-driven processes and classical click chemistry and have found applications ranging from surface functionalization, polymer conjugation, photo-crosslinking, and protein labeling. Despite these advances, the dependency of most of the photoclick reactions on UV light poses a severe obstacle for their general implementation, as this light can be absorbed by other molecules in the system resulting in their degradation or unwanted reactivity. However, the development of a simple and efficient system to achieve bathochromically shifted photoclick transformations remains challenging. Here, we introduce triplet-triplet energy transfer as a fast and selective way to enable visible light-induced photoclick reactions. Specifically, we show that 9,10-phenanthrenequinones (PQs) can efficiently react with electron-rich alkenes (ERAs) in the presence of a catalytic amount (as little as 5 mol %) of photosensitizers. The photocycloaddition reaction can be achieved under green (530 nm) or orange (590 nm) light irradiation, representing a bathochromic shift of over 100 nm as compared to the classical PQ-ERAs system. Furthermore, by combining appropriate reactants, we establish an orthogonal, blue and green light-induced photoclick reaction system in which the product distribution can be precisely controlled by the choice of the color of light.
Originele taal-2English
Artikelnummere202319321
Aantal pagina's9
TijdschriftAngewandte Chemie (International ed. in English)
Volume63
Nummer van het tijdschrift21
Vroegere onlinedatum12-apr.-2024
DOI's
StatusPublished - 21-mei-2024

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