Pseudo[3]rotaxane and [3]Rotaxane of Per(5-carboxy-5-dehydroxymethyl)-Cyclodextrins Utilizing Carboxylic Acid Dimer as Recognition Units

The formation of pseudo[3]rotaxane using dimers of per(5-carboxy-5-dehydroxymethyl)-cyclodextrins as ring components and secondary ammoniums as an axle is presented. This supramolecule is formed by the unique interaction of circularly arranged carboxylic acid dimers acting as hydrogen bonding acceptors covering the axle moiety. On these grounds, we could achieve the synthesis of the [3]rotaxane by capping the terminal groups through thiol-ene reactions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.joc.4c02804
Citations
8
Primary Topic
Supramolecular Chemistry and Complexes
Type
article
Field-Weighted Citation Impact
7.49

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article

Pseudo[3]rotaxane and [3]Rotaxane of Per(5-carboxy-5-dehydroxymethyl)-Cyclodextrins Utilizing Carboxylic Acid Dimer as Recognition Units

Takashi Nakamura, Tatsuya Nabeshima, Mauro Boero, Yasuteru Shigeta et al.
8 citations
The Journal of Organic Chemistry
Supramolecular Chemistry and Complexes
7.49
article

Pseudo[3]rotaxane and [3]Rotaxane of Per(5-carboxy-5-dehydroxymethyl)-Cyclodextrins Utilizing Carboxylic Acid Dimer as Recognition Units

Takashi Nakamura, Tatsuya Nabeshima, Mauro Boero, Yasuteru Shigeta, Masamune Kuwabara, Kazuki Okazawa, Haoyang Zhang
article en
8 citations

Abstract

The formation of pseudo[3]rotaxane using dimers of per(5-carboxy-5-dehydroxymethyl)-cyclodextrins as ring components and secondary ammoniums as an axle is presented. This supramolecule is formed by the unique interaction of circularly arranged carboxylic acid dimers acting as hydrogen bonding acceptors covering the axle moiety. On these grounds, we could achieve the synthesis of the [3]rotaxane by capping the terminal groups through thiol-ene reactions.

The Journal of Organic ChemistryVol. 90(10)
Centre National de la Recherche Scientifique (FR), University of Tsukuba (JP), Université de Strasbourg (FR)
Asahi Glass Foundation, Kurita Water and Environment Foundation, Université de Strasbourg, Saneyoshi Scholarship Foundation, Grand Équipement National De Calcul Intensif, Japan Society for the Promotion of Science, Research Institute for Information Technology, Kyushu University, Core Research for Evolutional Science and Technology, Precursory Research for Embryonic Science and Technology
Clean water and sanitation
Openalex Percentile: Top 3%
Supramolecular Chemistry and Complexes
7.49
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