ArticlePhotochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology2020
Aryl dechlorination and defluorination with an organic super-photoreductant.
Article in Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
18 citing papers in PubMed, 58 citations in OpenAlex.
- Kinetics vs Thermodynamics: Engineering Photoredox Reactivity from an Upper Excited State of FeJournal of the American Chemical Society · 2026Article
- Expanding Thermodynamic and Kinetic Frontiers in Molecular Photocatalysis.ACS central science · 2026Review
- Dramatic expansion of bimodal redox window of indigo by two-electron redox processes.Nature communications · 2025Article
- Excited Organic Radicals in Photoredox Catalysis.JACS Au · 2025Review
- Artificial Photosynthases: Single-Chain Nanoparticles with Manifold Visible-Light Photocatalytic Activity for Challenging "in Water" Organic Reactions.Journal of the American Chemical Society · 2024Article
- Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors.Beilstein journal of organic chemistry · 2023Review
- Accumulation of Four Electrons on a Terphenyl (Bis)disulfide.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Sensitizer-controlled photochemical reactivityChemical science · 2022Article
- Light-Driven Hydrodefluorination of Electron-Rich Aryl Fluorides by an Anionic Rhodium-Gallium Photoredox Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Mechanism of a Luminescent Dicopper System That Facilitates Electrophotochemical Coupling of Benzyl Chlorides via a Strongly Reducing Excited State.ACS catalysis · 2022Article
- Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals.Molecules (Basel, Switzerland) · 2022Review
- 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
- Red Light-Based Dual Photoredox Strategy Resembling the Z-Scheme of Natural Photosynthesis.JACS Au · 2022Article
- Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts.Chemical communications (Cambridge, England) · 2022Article
- C-P bond formation of cyclophanyl-, and aryl halidesRSC advances · 2022Article
- Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds.Chemical science · 2021Article
- Sensitization-initiated electron transferChemical science · 2021Article
- Photoactive electron donor-acceptor complex platform for Ni-mediated C(spChemical science · 2021Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Direct excitation of the commercially available super-electron donor tetrakis(dimethylamino)ethylene (TDAE) with light-emitting diodes at 440 or 390 nm provides a stoichiometric reductant that is able to reduce aryl chlorides and fluorides. The method is very simple and requires only TDAE, substrate, and solvent at room temperature. The photoactive excited state of TDAE has a lifetime of 17.3 ns in cyclohexane at room temperature and an oxidation potential of ca.-3.4 V vs. SCE. This makes TDAE one of the strongest photoreductants able to operate on the basis of single excitation with visible photons. Direct substrate activation occurs in benzene, but acetone is reduced by photoexcited TDAE and substrate reduction takes place by a previously unexplored solvent radical anion mechanism. Our work shows that solvent can have a leveling effect on the photochemically available redox power, reminiscent of the pH-leveling effect that solvent has in acid-base chemistry.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.