Design and Synthesis of Visible-Light-Responsive Azobenzene Building Blocks for Chemical Biology

Jana Volarić, Jeffrey Buter, Albert Schulte, Keimpe-Oeds van den Berg, Eduardo Santamaría-Aranda, Wiktor Szymanski, Ben Feringa

Research output: Contribution to journalArticleAcademicpeer-review


Tetra-ortho-fluoro-azobenzenes are a class of photoswitches useful for the construction of visible-light-controlled molecular systems. They can be used to achieve spatio-temporal control over the properties of a chosen bioactive molecule. However, the introduction of different substituents to the tetra-fluoro-azobenzene core can significantly affect the photochemical properties of the switch and compromise biocompatibility. Herein, we explored the effect of useful substituents, such as functionalization points, attachment handles, and water-solubilizing groups, on the photochemical properties of this photochromic system. In general, all the tested fluorinated azobenzenes exhibited favorable photochemical properties, such as high photostationary state distribution and long half-lives, both in organic solvents and in water. One of the azobenzene building blocks was functionalized with a trehalose group to enable the uptake of the photoswitch into mycobacteria. Following metabolic uptake and incorporation of the trehalose-based azobenzene in the mycobacterial cell wall, we demonstrated photoswitching of the azobenzene in the isolated total lipid extract.
Original languageEnglish
Pages (from-to)14319–14333
JournalThe Journal of Organic Chemistry
Issue number21
Publication statusPublished - 26 Oct 2022
Externally publishedYes


  • organic chemistry
  • photopharmacology
  • tuberculosis
  • immunology


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