Unraveling the Photoswitching Mechanism in Donor-Acceptor Stenhouse Adducts

Michael M. Lerch, Sander J. Wezenberg, Wiktor Szymanski, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

115 Citations (Scopus)
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Abstract

Molecular photoswitches have opened up a myriad of opportunities in applications ranging from responsive materials and control of biological function to molecular logics. Here, we show that the photoswitching mechanism of donor-acceptor Stenhouse adducts (DASA), a recently reported class of photoswitches, proceeds by photoinduced Z-E isomerization, followed by a thermal, conrotatory 4 pi-electrocyclization. The photogenerated intermediate is manifested by a bathochromically shifted band in the visible absorption spectrum of the DASA. The identification of the role of this intermediate reveals a key step in the photoswitching mechanism that is essential to the rational design of switching properties via structural modification.

Original languageEnglish
Pages (from-to)6344-6347
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number20
DOIs
Publication statusPublished - 25-May-2016

Keywords

  • AZA-PIANCATELLI REARRANGEMENT
  • VISIBLE-LIGHT
  • AZOBENZENE PHOTOSWITCHES
  • PHOSPHATE-BINDING
  • AZONIUM IONS
  • RED-LIGHT
  • IN-VIVO
  • SPIROPYRANS
  • SWITCHES
  • PHOTOCHROMISM

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