Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Aryl dechlorination and defluorination with an organic super-photoreductant

Author affiliations

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.

Graphical abstract: Aryl dechlorination and defluorination with an organic super-photoreductant

Back to tab navigation

Supplementary files

Article information


Submitted
04 Apr 2020
Accepted
23 Jun 2020
First published
26 Jun 2020

This article is Open Access

Photochem. Photobiol. Sci., 2020, Advance Article
Article type
Paper

Aryl dechlorination and defluorination with an organic super-photoreductant

F. Glaser, C. B. Larsen, C. Kerzig and O. S. Wenger, Photochem. Photobiol. Sci., 2020, Advance Article , DOI: 10.1039/D0PP00127A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements