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Improbable Rotaxanes Constructed From Surrogate Malonate Rotaxanes as Encircled Methylene Synthons

Chi‐You Tsai, Hung‐Te Cheng, Sheng‐Hsien Chiu

2023Angewandte Chemie International Edition15 citationsDOIOpen Access PDF

Abstract

We have developed a new approach for the synthesis of "improbable" rotaxanes by using malonate-centered rotaxanes as interlocked surrogate precursors. Here, the desired dumbbell-shaped structure can be assembled from two different, completely separate, portions, with the only residual structure introduced from the malonate surrogate being a methylene group. We have synthesized improbable [2]- and [3]rotaxanes with all-hydrocarbon dumbbell-shaped components to demonstrate the potential structural flexibility and scope of the guest species that can be interlocked when using this approach.

Topics & Concepts

SynthonMethyleneMalonateDumbbellFlexibility (engineering)RotaxaneNanotechnologyChemistryStereochemistryCombinatorial chemistryMaterials scienceCrystallographySupramolecular chemistryOrganic chemistryCrystal structureMathematicsMedicinePhysical therapyStatisticsSupramolecular Chemistry and ComplexesSupramolecular Self-Assembly in MaterialsCovalent Organic Framework Applications