Supramolecular Conformational Control of Aliphatic Oligoketones by Rotaxane Formation.

Org Lett

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan.

Published: April 2020


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Article Abstract

Conformational control of aliphatic oligoketones bearing two 1,3-diketone subunits is achieved by molecular recognition with pillar[5]arene. Pillar[5]arene binds to aliphatic ketones, with association constants of ∼10 M, to form pseudorotaxanes. The pseudorotaxanes are locked by BF complexation at the 1,3-diketone sites through quasi-solid-state reactions. X-ray crystallography reveals linear conformations for the axis molecules. The effect of supramolecular conformational restriction is evaluated using an alkyl-linked dyad chromophore system that shows solvatochromism upon intramolecular aggregation.

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http://dx.doi.org/10.1021/acs.orglett.0c01010DOI Listing

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