Diversely halogenated spiropyrans: Useful synthetic building blocks for a versatile class of molecular switches

Mathias Schulz-Senft, Paul J. Gates, Frank D. Sönnichsen, Anne C Staubitz

Research output: Contribution to journalArticle (Academic Journal)peer-review

9 Citations (Scopus)
618 Downloads (Pure)

Abstract

Spiropyrans are dyes that can be reversibly switched to a highly colored merocyanine form by a number of stimuli such as light, mechanical force or temperature. To make use of these molecules, there is a requirement to functionalize them appropriately. Herein we report a library of spiropyrans bearing two (pseudo) halide functional groups on either half of the molecule. Such halide substituents are valuable, because they themselves may be used as reactive sites in cross-coupling reactions, for example. Different combinations of halides, for which different reactivities in cross-coupling reactions may be expected, will facilitate selective consecutive cross-coupling reactions and condensations. Data concerning the UV/vis characteristics, the photostationary equilibria of the materials as well as the half-life of the merocyanine forms in solution are presented.
Original languageEnglish
Pages (from-to)292-301
Number of pages10
JournalDyes and Pigments
Volume136
Early online date21 Aug 2016
DOIs
Publication statusPublished - Jan 2017

Keywords

  • Molecular switch
  • Spiropyran
  • Organic synthesis
  • 3H-indole
  • Photochromism

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