Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization

David B. Konrad, James A. Frank, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Azobenzenes are versatile photoswitches that can be cycled between their trans- and cis-configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra-ortho-chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra-ortho-chloro azobenzenes has been developed, which relies on direct palladium(II)-catalyzed C-H activation of pre-existing standard azobenzenes. This late-stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red-AzCA-4, a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light.

Original languageEnglish (US)
Pages (from-to)4364-4368
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number13
DOIs
StatePublished - Mar 18 2016

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Azobenzene
Chlorination
Palladium
Isomerization
Cations
Positive ions
Chemical activation
Wavelength
azobenzene
Substrates

Keywords

  • azobenzene
  • C-H activation
  • halogenation
  • ion channels
  • photopharmacology

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization. / Konrad, David B.; Frank, James A.; Trauner, Dirk.

In: Chemistry - A European Journal, Vol. 22, No. 13, 18.03.2016, p. 4364-4368.

Research output: Contribution to journalArticle

Konrad, David B. ; Frank, James A. ; Trauner, Dirk. / Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 13. pp. 4364-4368.
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