Light-actuated resorcin[4]arene cavitands

Víctor García-López, Jovana V. Milić, Michal Zalibera, Dmytro Neshchadin, Martin Kuss-Petermann, Laurent Ruhlmann, Julia Nomrowski, Nils Trapp, Corinne Boudon, Georg Gescheidt, Oliver S. Wenger, François Diederich

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A light-actuated resorcin[4]arene cavitand equipped with two quinone (Q) and two opposite Ru(II)-based photosensitizing walls was synthesized and investigated. The cavitand is capable of switching from an open to a contracted conformation upon reduction of the two Q to the corresponding SQ radical anions by intramolecular photoinduced electron transfer in the presence of a sacrificial donor. The molecular switch was investigated by cyclic and rotating disc voltammetry, UV–Vis–NIR spectroelectrochemistry, transient absorption, NMR, and EPR spectroscopy. This study provides the basis for the development of future light-activated switches and molecular actuating nanodevices.

Original languageEnglish
Pages (from-to)5615-5626
Number of pages12
JournalTetrahedron
Volume74
Issue number39
DOIs
Publication statusPublished - 27 Sep 2018

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Keywords

  • Light-actuated cavitands
  • Resorcin[4]arene switches
  • Ruthenium-based cavitands
  • Semiquinone radical anion

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

García-López, V., Milić, J. V., Zalibera, M., Neshchadin, D., Kuss-Petermann, M., Ruhlmann, L., ... Diederich, F. (2018). Light-actuated resorcin[4]arene cavitands. Tetrahedron, 74(39), 5615-5626. https://doi.org/10.1016/j.tet.2018.08.002