Dataset Information

High Affinity Macrocycle Threading by a Near-Infrared Croconaine Dye with Flanking Polymer Chains.

ABSTRACT: Croconaine dyes have narrow and intense absorption bands at ∼800 nm, very weak fluorescence, and high photostabilities, which combine to make them very attractive chromophores for absorption-based imaging or laser heating technologies. The physical supramolecular properties of croconaine dyes have rarely been investigated, especially in water. This study focuses on a molecular threading process that encapsulates a croconaine dye inside a tetralactam macrocycle in organic or aqueous solvent. Macrocycle association and rate constant data are reported for a series of croconaine structures with different substituents attached to the ends of the dye. The association constants were highest in water (Ka ∼ 10(9) M(-1)), and the threading rate constants (kon) increased in the solvent order H2O > MeOH > CHCl3. Systematic variation of croconaine substituents located just outside the croconaine/macrocycle complexation interface hardly changed Ka but had a strong influence on kon. A croconaine dye with N-propyl groups at each end of the structure exhibited a desirable mixture of macrocycle threading properties; that is, there was rapid and quantitative croconaine/macrocycle complexation at relatively high concentrations in water, and no dissociation of the preassembled complex when it was diluted into a solution of fetal bovine serum, even after laser-induced photothermal heating of the solution. The combination of favorable near-infrared absorption properties and tunable mechanical stability makes threaded croconaine/macrocycle complexes very attractive as molecular probes or as supramolecular composites for various applications in absorption-based imaging or photothermal therapy.

SUBMITTER: Liu W

PROVIDER: S-EPMC4921234 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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High Affinity Macrocycle Threading by a Near-Infrared Croconaine Dye with Flanking Polymer Chains.

Liu Wenqi W Peck Evan M EM Smith Bradley D BD

The journal of physical chemistry. B 20160202 5

Croconaine dyes have narrow and intense absorption bands at ∼800 nm, very weak fluorescence, and high photostabilities, which combine to make them very attractive chromophores for absorption-based imaging or laser heating technologies. The physical supramolecular properties of croconaine dyes have rarely been investigated, especially in water. This study focuses on a molecular threading process that encapsulates a croconaine dye inside a tetralactam macrocycle in organic or aqueous solvent. Macr ...[more]

PMID: 26807599

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Dataset Information

High Affinity Macrocycle Threading by a Near-Infrared Croconaine Dye with Flanking Polymer Chains.

Publications

High Affinity Macrocycle Threading by a Near-Infrared Croconaine Dye with Flanking Polymer Chains.

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