Absolute configuration of a [1]rotaxane determined from vibrational and electronic circular dichroism spectra

Puente, Andrew R.; Bessaguet, Adrien; Pairault, Noël; Pieters, Grégory; Crassous, Jeanne; Polavarapu, Prasad L.; Opalinski, Isabelle; Papot, Sébastien

doi:10.1002/chir.23365

Chirality

2021

DOI: 10.1002/chir.23365

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Absolute configuration of a [1]rotaxane determined from vibrational and electronic circular dichroism spectra

Andrew R. Puente

Adrien Bessaguet

Noël Pairault

et al.

Abstract: The experimental vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) spectra were measured for the enantiomers of [1]rotaxane 1. These experimental spectra have been analyzed using predicted VCD and ECD spectra for (S, Rmp) or (S, Smp) diastereomers using density functional theory. This comparison allowed for a definitive assignment of the absolute configuration of 1.

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Cited by 2 publications

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An Interlocked Figure‐of‐Eight Molecular Shuttle

Gauthier,

Fournel‐Marotte,

Clavel

et al. 2023

Angewandte Chemie

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Here is reported the synthesis and characterization of an interlocked figure‐of‐eight rotaxane molecular shuttle from a dibenzo‐24‐crown‐8 (DB24C8) derivative. This latter bears two molecular chains, whose extremities are able to react together by click chemistry. One of the two substituting chain holds an ammonium function aimed at driving the self‐entanglement through the complexation of the DB24C8 moiety. In the targeted figure‐of‐eight rotaxane, shuttling of the DB24C8 along the threaded axle from the best ammonium station to the weaker binding site triazolium was performed through deprotonation‐then‐carbamoylation of the ammonium. This way, two discrete co‐conformational states were obtained, in which the folding and size of the two loops could be changed.

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An Interlocked Figure‐of‐Eight Molecular Shuttle

Gauthier,

Fournel‐Marotte,

Clavel

et al. 2023

Angewandte Chemie

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show abstract

An Interlocked Figure‐of‐Eight Molecular Shuttle

Gauthier,

Fournel‐Marotte,

Clavel

et al. 2023

Angew Chem Int Ed

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Absolute configuration of a [1]rotaxane determined from vibrational and electronic circular dichroism spectra

Cited by 2 publications

References 38 publications

An Interlocked Figure‐of‐Eight Molecular Shuttle

An Interlocked Figure‐of‐Eight Molecular Shuttle

An Interlocked Figure‐of‐Eight Molecular Shuttle

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