Structural Control of Kinetics for Macrocycle Threading by Fluorescent Squaraine Dye in Water

Structural Control of Kinetics for Macrocycle Threading by Fluorescent Squaraine Dye in Water

While the general concept of steric speed bumps has been demonstrated in rotaxane shuttles and macrocycle threading systems, the sensitivity of speed bump effects has not been evaluated as a function of structural geometry. Values of K a and k on for macrocycle threading in water are reported for a...

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Veröffentlicht in:Journal of organic chemistry 2017-08, Vol.82 (16), p.8334-8341
Hauptverfasser: Gómez-Durán, César F. A, Liu, Wenqi, Betancourt-Mendiola, María de Lourdes, Smith, Bradley D
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container_issue 16
container_start_page 8334
container_title Journal of organic chemistry
container_volume 82
creator Gómez-Durán, César F. A
Liu, Wenqi
Betancourt-Mendiola, María de Lourdes
Smith, Bradley D
description While the general concept of steric speed bumps has been demonstrated in rotaxane shuttles and macrocycle threading systems, the sensitivity of speed bump effects has not been evaluated as a function of structural geometry. Values of K a and k on for macrocycle threading in water are reported for a series of homologous squaraine dyes with different substituents (speed bumps) on the flanking chains and two macrocycles with different cavity sizes. Sensitivity to a steric speed bump effect was found to depend on (a) structural location, being lowest when the speed bump was near the end of a flanking chain, and (b) macrocycle cavity size, which was enhanced when the cavity was constricted. This new insight is broadly applicable to many types of molecular threading systems.
doi_str_mv 10.1021/acs.joc.7b01486
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title Structural Control of Kinetics for Macrocycle Threading by Fluorescent Squaraine Dye in Water
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