Linear and rectangular [n]rotaxanes were synthesized by template-directed clipping of heterocrown ether components onto the dumbbell-shaped molecules containing different dialkylammonium recognition sites. The effect of the structure of the dialkylammonium sites on the clipping efficiency was investigated, and selective clipping led to formation of a rectangular [4]rotaxane.
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Angew Chem Int Ed Engl
August 2023
Department of Chemistry, University of Utah, 315 South 1400 East, Room 2020, Salt Lake City, UT 84112, USA.
Macrocyclic molecule-based host-guest systems, which provide contributions for the design and construction of functional supramolecular structures, have gained increasing attention in recent years. In particular, platinum(II) metallacycle-based host-guest systems provide opportunities for chemical scientists to prepare novel materials with various functions and structures due to the well-defined shapes and cavity sizes of platinum(II) metallacycles. However, the research on platinum(II) metallacycle-based host-guest systems has been given little attention.
View Article and Find Full Text PDFDalton Trans
September 2021
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK.
A novel halogen bonding (XB) bis(iodotriazole)-imidazolium motif is incorporated into the axle component of a [2]rotaxane a discrete chloride anion template directed clipping methodology. H NMR anion titration experiments reveal the interlocked host is capable of strong halide and sulfate oxoanion binding in competitive aqueous-organic CDCl/CDOD/DO (45 : 45 : 10 v/v) solvent mixtures. In comparison to a hydrogen bonding rotaxane analogue, which exhibited no pronounced selectivity between Cl, I and SO, the axle iodo-triazole donor motifs of the XB rotaxane modulate the anion recognition preference towards the lighter halides Cl ≈ Br > SO > I.
View Article and Find Full Text PDFOrg Lett
August 2020
Department of Chemistry, Organic Chemistry Section, Jadavpur University, Kolkata 700032, India.
The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.
View Article and Find Full Text PDFOrg Biomol Chem
November 2016
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
Supramolecular chemistry and self-assembly provide a valuable chance to understand the complicated topological structures on a molecular level. Two types of classical mechanically interlocked molecules, rotaxanes and catenanes, possess non-covalent mechanical bonds and have attracted more attention not only in supramolecular chemistry but also in the fields of materials science, nanotechnology and bioscience. In the past decades, the template-directed clipping reaction based on imine chemistry has become one of the most efficient methods for the construction of functionalized rotaxanes and catenanes.
View Article and Find Full Text PDFOrg Biomol Chem
October 2015
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China.
Tetraphenylethene (TPE) with aggregation-induced emission (AIE) behavior as a popular backbone is applied widely in the construction of functional supramolecular systems. In this work, a TPE-based linear molecule having amide and amine units is synthesized. Its ammonium template is used to construct the N-hetero crown ether-based [2]rotaxane by the template-directed clipping approach.
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