Host−[2]Rotaxane:  Advantage of Converging Functional Groups for Guest Recognition

Smukste, Inese; House, Brian E.; Smithrud, David B.

doi:10.1021/jo026522+

Cited by 46 publications

(22 citation statements)

References 47 publications

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“…In view of these examples, it is astonishing that the larger calix[8]arene was not yet used as a macrocyclic component in rotaxanes or catenanes. Calix [4] arenes have been used, however, as stoppers in rotaxanes [76], where they can contribute to the binding of guests [77].…”

Section: Discussionmentioning

confidence: 99%

Tetra‐Urea Calix[4]arenes — From Dimeric Capsules to Novel Catenanes and Rotaxanes

Podoprygorina

Böhmer

2008

Modern Supramolecular Chemistry

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The preparation of topologically interesting molecules and supramolecular structures such as catenanes, knots [1], or Möbius strips [2] is primarily an intellectual challenge, although more and more applications [3] have been proposed during the last decade(s). The synthesis of structures consisting of interlocked rings usually requires the formation of cyclic molecules from linear precursors while they are penetrating already existing rings. Similarly to the macroscopic example (the fabrication of a chain [Latin: catena]), an efficient synthesis of catenanes 1) requires a perfect prearrangement of the respective building blocks. On the molecular level, such a preorganization can be achieved by an appropriate covalent linkage which has to be cleaved after the intended ring-closure reaction(s). However, the desired mutual arrangement of the precursors can also be obtained via reversible links, such as coordination to metal cations, hydrogen bonding, or interactions of the donoracceptor type. This has the advantage that wrong connections can be corrected during the assembly process. The rapid progress in the synthesis of topologically more and more demanding molecules and complex structures in reasonable yields, for which Borromean rings [4] represent an impressive example, is therefore strongly connected with the development of supramolecular chemistry in general [5].The first rational synthesis of a [2]catenane was reported by Schill and Lüttrin-ghaus [6], who successfully used a covalent attachment to a template. This covalent approach was recently applied by Godt and coworkers for the preparation of a series of [2]catenanes consisting of really large and thus mutually mobile chain rings (non-rusty catenanes) [7]. In this case a prefabricated macrocycle and a precursor for the second ring were linked via a carbonate group. The oxidative coupling of the alkyne residues formed the second cycle, which has to be threaded through the first one (Scheme 5.1). Hydrolysis of the carbonate linkage disconnected the two rings, producing a [2]catenane.

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Section: Discussionmentioning

confidence: 99%

Tetra‐Urea Calix[4]arenes — From Dimeric Capsules to Novel Catenanes and Rotaxanes

Podoprygorina

Böhmer

2008

Modern Supramolecular Chemistry

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“…Thus, they synthesized multiple crown ethers with different pending groups, including amino acids, and studied their ability to act as artificial receptors. Structure-properties relationship has also been studied in regard to the binding ability [74]. These so-called host- [2]rotaxanes have been tested as cellular transport agent for fluorescein-PKC inhibitor conjugate [75][76][77][78].…”

Section: Bioactive Rotaxanesmentioning

confidence: 99%

Recent Advances in the Synthesis of Ammonium-Based Rotaxanes

Thibeault

Morin

2010

Molecules

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Abstract:The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years. The challenge in the synthesis of rotaxanes results from the rather weak interactions between the ammonium-containing rod and the crown ether macrocycle in the pseudorotaxane structure that rely mostly on O·H hydrogen bonds. Indeed, no strong base or polar solvent that could break up H-bonding can be used during the formation of rotaxanes because the two components will separate as two distinct entities. Moreover, most of the reactions have to be performed at room temperature to favor the formation of pseudorotaxane in solution. These non-trivial prerequisites have been taken into account to develop efficient reaction conditions for the preparation of rotaxanes and those are described in detail along this review.

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“…However, they are better site of recognitions than the amine moiety that directly derives from deprotonation of the best ammonium station, allowing the pH-sensitive actuation of the molecular machinery. To the best of our knowledge, although one can find in the literature some DB24C8-containing [2]rotaxanes that involve amide moieties [ 3 , 53 , 54 , 55 ], only a few studies have investigated the utilization of a single secondary amide moiety as an efficient secondary molecular station for the DB24C8 [ 56 , 57 ]. In this paper, we straightforwardly synthesized [2]rotaxane molecular shuttles that combine a strong ammonium station and either a secondary or a tertiary amide station.…”

Section: Introductionmentioning

confidence: 99%

How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?

et al. 2017

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Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions for crown ethers, the very straightforwardly obtained amide motif has more rarely been envisaged as molecular station. In this article, we report the use of secondary and tertiary amide moieties as efficient secondary molecular station in pH-sensitive molecular shuttles. Depending on the N-substitution of the amide station, and on deprotonation or deprotonation-carbamoylation, the actuation of the molecular machinery differs accordingly to very distinct interactions between the axle and the DB24C8.

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Host−[2]Rotaxane: Advantage of Converging Functional Groups for Guest Recognition

Cited by 46 publications

References 47 publications

Tetra‐Urea Calix[4]arenes — From Dimeric Capsules to Novel Catenanes and Rotaxanes

Tetra‐Urea Calix[4]arenes — From Dimeric Capsules to Novel Catenanes and Rotaxanes

Recent Advances in the Synthesis of Ammonium-Based Rotaxanes

How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?

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