Anion- and Solvent-Induced Rotary Dynamics and Sensing in a Perylene Diimide [3]Catenane

Liliana Ferreira, Igor Marques, Vítor Félix, Paul D. Beer, Timothy Barendt

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)
198 Downloads (Pure)

Abstract

A novel dynamic [3]catenane consisting of a large four-station central macrocycle which incorporates a bay tetrachloro-functionalized perylene diimide (PDI) unit and two triazolium anion-binding motifs, mechanically bonded with two smaller isophthalamide-containing macrocycles, is constructed using an anion template synthetic methodology. Proton NMR, electronic absorption, and fluorescence emission spectroscopies together with molecular dynamics simulations are used to investigate the anion recognition- and solvent-dependent dynamic properties of the higher-order mechanically interlocked molecule. Importantly, unprecedented solvent-dependent and anion-binding-induced circumrotatory motion in a hetero[3]catenane system is demonstrated where the exotic dual rotary switching behavior provides a unique and sophisticated mechanism for optical anion sensing in competitive protic organic and aqueous-organic media.

Original languageEnglish
Pages (from-to)9026-9037
Number of pages12
JournalJournal of the American Chemical Society
Volume139
Issue number26
Early online date7 Jun 2017
DOIs
Publication statusPublished - 5 Jul 2017

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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