Direct and Versatile Synthesis of Red-Shifted Azobenzenes

Mickel J. Hansen, Michael M. Lerch, Wiktor Szymanski*, Ben L. Feringa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

90 Citations (Scopus)
27 Downloads (Pure)

Abstract

A straightforward synthesis of azobenzenes with bathochromically-shifted absorption bands is presented. It employs an ortho-lithiation of aromatic substrates, followed by a coupling reaction with aryldiazonium salts. The products are obtained with good to excellent yields after simple purification. Moreover, with the presented methodology, a structurally diverse panel of different azobenzenes, including unsymmetric tetra-ortho-substituted ones, can be readily obtained, which paves the way for future development of red-light-addressable azobenzene derivatives for in vivo application.

Original languageEnglish
Pages (from-to)13514-13518
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number43
DOIs
Publication statusPublished - 17-Oct-2016

Keywords

  • azobenzenes
  • diazonium salts
  • lithiation
  • photochromism
  • red shift
  • GLUTAMATE-RECEPTOR
  • ORTHO-METALATION
  • OPTICAL CONTROL
  • VISIBLE-LIGHT
  • AZONIUM IONS
  • IN-VIVO
  • PHOTOSWITCHES
  • PHOTOPHARMACOLOGY
  • INHIBITORS
  • SWITCHES

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