Stepwise Functionalization of a Pillar (5) arene‐Containing (2) Rotaxane with Pentafluorophenyl Ester Stoppers
Abstract: Detailed investigations into the stepwise bis‐functionalization of a pillar[5]arene‐containing rotaxane building block have been carried out. Upon a first stopper exchange, the pillar[5]arene moiety of the mono‐acylated product is preferentially located close to its reactive pentafluorophenyl ester stopper, thus limiting the accessibility to the reactive carbonyl group by the nucleophilic reagents. Selective mono‐functionalization is thus very efficient. Introduction of a second stopper is then possible to generate dissymmetrical rotaxanes with different amide stoppers. Moreover, when dethreading is possible upon the second acylation, the pillar[5]arene plays the role of a protecting group allowing the synthesis of dissymmetrical axles that are particularly difficult to prepare under statistical conditions. Finally, detailed conformation analysis of the rotaxanes revealed that the position of the pillar[5]arene moiety on its axle subunit is mainly governed by polar interactions in nonpolar organic solvents, whereas solvophobic effects play a major role in polar solvents.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Stepwise Functionalization of a Pillar (5) arene‐Containing (2) Rotaxane with Pentafluorophenyl Ester Stoppers ; day:21 ; month:12 ; year:2023 ; extent:13
Chemistry - a European journal ; (21.12.2023) (gesamt 13)
- Urheber
-
Becharguia, Nihed
Wasielewski, Emeric
Abidi, Rym
Nierengarten, Iwona
Nierengarten, Jean‐François
- DOI
-
10.1002/chem.202303501
- URN
-
urn:nbn:de:101:1-2023122114362391818741
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:36 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Becharguia, Nihed
- Wasielewski, Emeric
- Abidi, Rym
- Nierengarten, Iwona
- Nierengarten, Jean‐François
Ähnliche Objekte (12)
Diversity Oriented Preparation of Pillar (5) arene‐Containing (2) Rotaxanes by a Stopper Exchange Strategy
Multistimuli Sensitive Behavior of Novel Bodipy‐Involved Pillar (5) arene‐Based Fluorescent (2) Rotaxane and Its Supramolecular Gel
Solution and Solvent‐Free Stopper Exchange Reactions for the Preparation of Pillar (5) arene‐containing (2) and (3) Rotaxanes
Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes
Partially Sulfated Pillar (5) Arenes: Synthesis and Molecular Recognition Properties
Cavity-promotion by pillar[5]arenes expedites organic photoredox-catalysed reductive dehalogenations
Neuartige photoschaltbare Rotaxane
Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface
N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe3+ sensing
Molecular weight fractionation by confinement of polymer in one-dimensional pillar[5]arene channels
Spacer Length‐Independent Shuttling of the Pillar (5) arene Ring in Neutral (2) Rotaxanes
Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water
Diversity Oriented Preparation of Pillar (5) arene‐Containing (2) Rotaxanes by a Stopper Exchange Strategy
Multistimuli Sensitive Behavior of Novel Bodipy‐Involved Pillar (5) arene‐Based Fluorescent (2) Rotaxane and Its Supramolecular Gel
Solution and Solvent‐Free Stopper Exchange Reactions for the Preparation of Pillar (5) arene‐containing (2) and (3) Rotaxanes
Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes
Partially Sulfated Pillar (5) Arenes: Synthesis and Molecular Recognition Properties
Cavity-promotion by pillar[5]arenes expedites organic photoredox-catalysed reductive dehalogenations
Neuartige photoschaltbare Rotaxane
Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface
N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe3+ sensing
Molecular weight fractionation by confinement of polymer in one-dimensional pillar[5]arene channels
Spacer Length‐Independent Shuttling of the Pillar (5) arene Ring in Neutral (2) Rotaxanes
Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water
Diversity Oriented Preparation of Pillar (5) arene‐Containing (2) Rotaxanes by a Stopper Exchange Strategy
Multistimuli Sensitive Behavior of Novel Bodipy‐Involved Pillar (5) arene‐Based Fluorescent (2) Rotaxane and Its Supramolecular Gel
Solution and Solvent‐Free Stopper Exchange Reactions for the Preparation of Pillar (5) arene‐containing (2) and (3) Rotaxanes
Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes
Partially Sulfated Pillar (5) Arenes: Synthesis and Molecular Recognition Properties
Cavity-promotion by pillar[5]arenes expedites organic photoredox-catalysed reductive dehalogenations
Neuartige photoschaltbare Rotaxane
Ring shape-dependent self-sorting of pillar[n]arenes assembled on a surface
N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe3+ sensing
Molecular weight fractionation by confinement of polymer in one-dimensional pillar[5]arene channels
Spacer Length‐Independent Shuttling of the Pillar (5) arene Ring in Neutral (2) Rotaxanes