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*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

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.
Original languageEnglish
Article numbere202319321
Number of pages9
JournalAngewandte Chemie (International ed. in English)
Volume63
Issue number21
Early online date12-Apr-2024
DOIs
Publication statusPublished - 21-May-2024

Keywords

  • Triplet-Triplet Energy Transfer
  • Photoclick
  • Photochemistry
  • Phenanthrenequinone
  • Orthogonality

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