Arylazoindazole Photoswitches: Facile Synthesis and Functionalization via SNAr Substitution

Raquel Travieso-Puente, Simon Budzak, Juan Chen, Peter Stacko, Johann T B H Jastrzebski, Denis Jacquemin, Edwin Otten

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Abstract

A straightforward synthetic route to arylazoindazoles via nucleophilic aromatic substitution is presented. Upon deprotonation of the NH group, a C6F5-substituted formazan undergoes facile cyclization as a result of intermolecular nucleophilic substitution (SNAr). This new class of azo photoswitches containing an indazole five-membered heterocycle shows photochemical isomerization with high fatigue resistance. In addition, the Z-isomers have long thermal half-lives in the dark of up to several days at room temperature. The fluorinated indazole group offers a handle for further functionalization and tuning of its properties, as it is shown to be susceptible to a subsequent, highly selective nucleophilic displacement reaction.

Original languageEnglish
Pages (from-to)3328-3331
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number9
DOIs
Publication statusPublished - 2017

Keywords

  • Journal Article

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