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Active-Metal Template Synthesis of a Halogen-Bonding Rotaxane for Anion Recognition.

ABSTRACT: The synthesis of an all-halogen-bonding rotaxane for anion recognition is achieved by using active-metal templation. A flexible bis-iodotriazole-containing macrocycle is exploited for the metal-directed rotaxane synthesis. Endotopic binding of a Cu(I) template facilitates an active-metal CuAAC iodotriazole axle formation reaction that captures the interlocked rotaxane product. Following copper-template removal, exotopic coordination of a more sterically demanding rhenium(I) complex induces an inversion in the conformation of the macrocycle component, directing the iodotriazole halogen-bond donors into the rotaxane's interlocked binding cavity to facilitate anion recognition.

SUBMITTER: Langton MJ

PROVIDER: S-EPMC4736451 | biostudies-other | 2015 Dec

REPOSITORIES: biostudies-other

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Active-Metal Template Synthesis of a Halogen-Bonding Rotaxane for Anion Recognition.

Langton Matthew J MJ Xiong Yaoyao Y Beer Paul D PD

Chemistry (Weinheim an der Bergstrasse, Germany) 20151120 52

The synthesis of an all-halogen-bonding rotaxane for anion recognition is achieved by using active-metal templation. A flexible bis-iodotriazole-containing macrocycle is exploited for the metal-directed rotaxane synthesis. Endotopic binding of a Cu(I) template facilitates an active-metal CuAAC iodotriazole axle formation reaction that captures the interlocked rotaxane product. Following copper-template removal, exotopic coordination of a more sterically demanding rhenium(I) complex induces an in ...[more]

PMID: 26500150

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