1. Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing
- Author
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Zongyao Zhang, Yuen Cheong Tse, Edward J. Mitchell, Robert Hein, and Paul D. Beer
- Subjects
Anions ,Boron Compounds ,Rotaxane ,Fluorophore ,Porphyrins ,Rotaxanes ,Hot Paper ,Photochemistry ,Redox ,Catalysis ,chemistry.chemical_compound ,Halogens ,BODIPY ,Anion binding ,Halogen bond ,Quenching (fluorescence) ,Full Paper ,Organic Chemistry ,anion sensing ,electrochemical sensing ,Hydrogen Bonding ,General Chemistry ,Full Papers ,Porphyrin ,optical sensing ,chemistry - Abstract
Anion receptors employing two distinct sensory mechanisms are rare. Herein, we report the first examples of halogen‐bonding porphyrin BODIPY [2]rotaxanes capable of both fluorescent and redox electrochemical sensing of anions. 1H NMR, UV/visible and electrochemical studies revealed rotaxane axle triazole group coordination to the zinc(II) metalloporphyrin‐containing macrocycle component, serves to preorganise the rotaxane binding cavity and dramatically enhances anion binding affinities. Mechanically bonded, integrated‐axle BODIPY and macrocycle strapped metalloporphyrin motifs enable the anion recognition event to be sensed by the significant quenching of the BODIPY fluorophore and cathodic perturbations of the metalloporphyrin P/P+. redox couple., The first examples of porphyrin‐BODIPY halogen bonding [2]rotaxanes have been prepared according to an active metal template strategy. Capitalising on the augmented anion affinities by virtue of axle triazole ligation to macrocyclic zinc(II) metalloporphyrin, the incorporation of fluorogenic BODIPY and redox‐active porphyrin transducing groups allows dual‐channel sensing of anions by quenching BODIPY emission and through cathodic perturbations of porphyrin oxidation redox couples.
- Published
- 2021