Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 26, Pages 9026-9037Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04295
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Funding
- CICECO-Aveiro Institute of Materials [UID/CTM/50011/2013]
- iBiMED-Institute of Biomedicine [UID/BIM/04501/2013]
- National Funds through the FCT/MEC
- FEDER through COMPETE
- FCT [SFRH/BD/87520/2012]
- EPSRC
- Christ Church, University of Oxford
- [P2020-PTDC/QEQ-SUP/4283/2014]
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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.
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