ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding - Enhancement of the Key Step by the Internal Heavy Atom Effect.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Flavin Catalysts in Organic Synthesis.Angewandte Chemie (International ed. in English) · 2026Review
- Photophysical properties and acid-base equilibria of lumichrome anions in nonaqueous media.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Article
- Deazaalloxazines - Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Introduction of flavin anions into photoredox catalysis: acid-base equilibria of lumichrome allow photoreductions with an anion of an elusive 10-unsubstituted isoalloxazine.Chemical science · 2025Article
- Effect of Excitation Wavelength in Single-Molecule Photochemistry of Terrylene.Chemphyschem : a European journal of chemical physics and physical chemistry · 2025Article
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts.Beilstein journal of organic chemistry · 2024Article
- Shining Fresh Light on Complex Photoredox Mechanisms through Isolation of Intermediate Radical Anions.ACS catalysis · 2023Article
- Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding - Enhancement of the Key Step by the Internal Heavy Atom Effect.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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7 authors.
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Abstract
Deazaflavins are well suited for reductive chemistry acting via a consecutive photo-induced electron transfer, in which their triplet state and semiquinone - the latter is formed from the former after electron transfer from a sacrificial electron donor - are key intermediates. Guided by mechanistic investigations aiming to increase intersystem crossing by the internal heavy atom effect and optimising the concentration conditions to avoid unproductive excited singlet reactions, we synthesised 5-aryldeazaflavins with Br or Cl substituents on different structural positions via a three-component reaction. Bromination of the deazaisoalloxazine core leads to almost 100 % triplet yield but causes photo-instability and enhances unproductive side reactions. Bromine on the 5-phenyl group in ortho position does not affect the photostability, increases the triplet yield, and allows its efficient usage in the photocatalytic dehalogenation of bromo- and chloroarenes with electron-donating methoxy and alkyl groups even under aerobic conditions. Reductive powers comparable to lithium are achieved.
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