A new tetralactam macrocycle was prepared and found to encapsulate deep-red and near-infrared squaraine and croconaine dyes in water with tunable threading kinetics. The new supramolecular paradigm of guest back-folding was used to increase macrocycle/squaraine affinity by 370-fold and achieve an association constant of 2.8 × 10 M.
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http://dx.doi.org/10.1039/c9cc05244e | DOI Listing |
The complex distribution of functional groups in carbohydrates, coupled with their strong solvation in water, makes them challenging targets for synthetic receptors. Despite extensive research into various molecular frameworks, most synthetic carbohydrate receptors have exhibited low affinities, and their interactions with sugars in aqueous environments remain poorly understood. In this work, we present a simple pyridinium-based hydrogen-bonding receptor derived from a subtle structural modification of a well-known tetralactam macrocycle.
View Article and Find Full Text PDFCommun Chem
October 2024
Institut für Chemie und Biochemie, Freie Universität Berlin, Arnimallee 20, 14195, Berlin, Germany.
In nature, molecular environments in proteins can sterically protect and stabilize reactive species such as organic radicals through non-covalent interactions. Here, we report a near-infrared fluorescent rotaxane in which the stabilization of a chemically labile squaraine fluorophore by the coordination of a tetralactam macrocycle can be controlled chemically and electrochemically. The rotaxane can be switched between two co-conformations in which the wheel either stabilizes or exposes the fluorophore.
View Article and Find Full Text PDFDalton Trans
June 2023
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology (BIST), Avgda. Països Catalans, 16, 43007 Tarragona, Spain.
We report the self-assembly of a robust di-nuclear tetralactam macrocyle based on two symmetric components: a Rh(III) bis-porphyrin and a bis-pyridyl ligand. We probe the binding properties of the tetralactam macrocycle with adipamide derivatives using H NMR spectroscopy. On the one hand, we show that the binding of the adipamide having linear alkyl chains that can thread through the intact macrocycle's cavity produces a weakly bound 1 : 1 complex stabilized by four intermolecular hydrogen bonds and featuring a preferred binding geometry of [2]pseudorotaxane topology.
View Article and Find Full Text PDFChem Commun (Camb)
May 2023
School of Pharmaceutical Science, Postdoctoral Research Station of Basic Medicine, Hengyang Medical School, University of South China, Hengyang, Hunan, 421001, China.
An indicator displacement assay for colorimetric and fluorometric dual-mode detection of urinary uric acid (UA) was constructed using a water-soluble naphthalene-based tetralactam macrocycle and the phenoxazine dye, resorufin (RF). The visual detection of UA levels of volunteers was successfully realized using modified paper assays, which could be used for the home monitoring of urinary UA.
View Article and Find Full Text PDFChem Commun (Camb)
December 2021
Shenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis and Department of Chemistry, Southern University of Science and Technology, Xueyuan Blvd 1088, Shenzhen, 518055, China.
A water-soluble tetralactam macrocycle with 2,6-diethoxynaphthalene groups as side walls is able to strongly bind riboflavin ( >10 M) in water through hydrogen bonding and the hydrophobic effect. The encapsulated riboflavin can be stabilized by the host against photo-degradation under UV-vis irradiation, which may be harnessed to extend the shelf life of riboflavin.
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