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• W2894250819 endingPage "13834" @default.
• W2894250819 startingPage "13827" @default.
• W2894250819 abstract "The redox properties of cyclobis(paraquat-p-phenylene)cyclophane (CBPQT4+) render it a uniquely variable source of recognition in the context of mechanically interlocked molecules, through aromatic donor–acceptor interactions in its fully oxidized state (CPBQT4+) and radical-pairing interactions in its partially reduced state (CBPQT2(•+)). Although it is expected that the fully reduced neutral state (CBPQT(0)) might behave as a π-donating recognition unit, resulting in a dramatic change in its binding properties when compared with the other two redox states, its role in rotaxanes has not yet been investigated. To address this challenge, we report herein the synthesis of a tri-stable [2]rotaxane in which a CBPQT4+ ring is mechanically interlocked with a dumbbell component containing five recognition sites—(i) a bipyridinium radical cation (BIPY(•+)) located centrally along the axis of the dumbbell, straddled by (ii) two tetrafluorophenylene units linked to (iii) two triazole rings. In addition to the selective recognition between (iv) the CBPQT4+ ring and the triazole units, and (v) the CBPQT2(•+) ring and the reduced BIPY(•+) unit in the dumbbell component, investigations in solution have now confirmed the presence of additional non-covalent bonding interactions between the CBPQT(0) ring, acting as a donor in its neutral state, and the two tetrafluorophenylene acceptors in the dumbbell component. The unveiling of this piece of molecular recognition in a [2]rotaxane is reminiscent of the existence in much simpler, covalently linked, organic molecules of neighboring group participation (anchimeric assistance giving way to transannular interactions) in small-, medium-, and large-membered rings." @default.
• W2894250819 created "2018-10-05" @default.
• W2894250819 creator A5001838489 @default.
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• W2894250819 date "2018-09-25" @default.
• W2894250819 modified "2023-10-10" @default.
• W2894250819 title "Neighboring Component Effect in a Tri-stable [2]Rotaxane" @default.
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• W2894250819 doi "https://doi.org/10.1021/jacs.8b08519" @default.
• W2894250819 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30253106" @default.
• W2894250819 hasPublicationYear "2018" @default.
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