Photocontrol of Anion Binding Affinity to a Bis-urea Receptor Derived from Stiff-Stilbene

Sander J. Wezenberg*, Ben L. Feringa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Toward the development of photoresponsive anion receptors, a stiff-stilbene photoswitch has been equipped' with two urea anion -binding motifs. Photoinduced E/Z isomerization has been studied in detail by UV-vis and NMR spectroscopy. Titration experiments (H-1 NMR) reveal strong binding of acetate and phosphate to the (Z)-isomer, in which the urea groups are closely together. Isomerization to the (E)-form separates the urea motifs, resulting in much weaker binding. Additionally, geometry optimizations by density functional theory (DFT) illustrate that oxo-anion binding to the (Z)-form involves four hydrogen bonds.

Original languageEnglish
Pages (from-to)324-327
Number of pages4
JournalOrganic letters
Volume19
Issue number2
DOIs
Publication statusPublished - 20-Jan-2017

Keywords

  • PHOTOSWITCHABLE PROPERTIES
  • HALIDE ANIONS
  • RELEASE
  • FOLDAMER
  • CHLORIDE
  • HOST
  • RECOGNITION
  • MOLECULES
  • POLYMERS
  • SWITCH

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