Vinyl sulfonyl chemistry-driven unidirectional transport of a macrocycle through a [2]rotaxane

David, Arthur H. G.; García‐Cerezo, Pablo; Campaña, Araceli G.; Santoyo‐González, Francisco; Blanco, Víctor Francisco Sampedro

doi:10.1039/d1qo01491a

Cited by 15 publications

(5 citation statements)

References 79 publications

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“…As the reaction for the capping step, we chose the Michael-type addition reaction to the vinyl sulfonyl group . As we previously demonstrated, this reaction has been shown to be efficient and versatile in the synthesis of rotaxanes, , including examples based on pillar[5]arene and the binding unit proposed here . In order to apply this strategy, we designed a hept -HBC derivative (compound 3 ) bearing a vinyl sulfone group attached to the aromatic core through an aliphatic linker.…”

Section: Resultsmentioning

confidence: 99%

Curved Nanographenes as Stoppers in a [2]Rotaxane with Two-Photon Excited Emission

Codesal,

David,

Santos

et al. 2024

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Curved Nanographenes as Stoppers in a [2]Rotaxane with Two-Photon Excited Emission

Codesal,

David,

Santos

et al. 2024

J. Org. Chem.

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“…A similar process has also been used in a linear rotaxane‐based ratchet, showing that the distribution of a macrocycle could be moved away from equilibrium [53a] . A related system for relative linear transport of components has been achieved by Blanco using orthogonal vinyl sulfonyl chemistry [36b] …”

Section: Energy Ratchetsmentioning

confidence: 99%

“…Kinetically defining a region on a potential energy surface within which statistically driven motion can occur, controls the directionality and is achieved by switching barrier heights. This can be achieved by an orthogonal process [36a–c] (generally requiring additional manipulations, Section 2.2). It is possible to reduce the number of steps required by designing a system where the same stimulus changes both relative well depths and relative barrier heights on the potential energy surface (Section 2.3).…”

Section: The Design Of Molecular Ratchetsmentioning

confidence: 99%

Molecular Ratchets and Kinetic Asymmetry: Giving Chemistry Direction

Borsley,

Leigh,

Roberts

2024

Angew Chem Int Ed

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In recent years ratchet mechanisms have transformed the understanding and design of stochastic molecular systems—biological, chemical and physical—in a move away from the mechanical macroscopic analogies that dominated thinking regarding molecular dynamics in the 1990s and early 2000s (e.g. pistons, springs, etc), to the more scale‐relevant concepts that underpin out‐of‐equilibrium research in the molecular sciences today. Ratcheting has established molecular nanotechnology as a research frontier for energy transduction and metabolism, and has enabled the reverse engineering of biomolecular machinery, delivering insights into how molecules ‘walk’ and track‐based synthesizers operate, how the acceleration of chemical reactions enables energy to be transduced by catalysts, and how dynamic (supra)molecular systems can be driven away from equilibrium. The recognition of molecular ratchet mechanisms in biology, and their invention in synthetic systems, is proving significant in areas as diverse as supramolecular chemistry, systems chemistry, dynamic covalent chemistry, DNA nanotechnology, polymer and materials science, molecular biology, heterogeneous catalysis, endergonic synthesis, and many other branches of chemical science. Put simply, ratchet mechanisms give chemistry direction. Kinetic asymmetry, quantified by the outcome of ratcheting, is the dynamic counterpart of structural asymmetry (i.e. chirality). Given the ubiquity of ratchet mechanisms, it is surely just as fundamentally important.

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“…Thus, different reversible and irreversible dethreading strategies have been reported, [36][37][38][39][40][41][42][43] operating through the application of different stimuli, such as light, pH and chemical inputs. Indeed, a number of applications in which such processes are mandatory have been carried out by different researchers in the area of molecular machines.…”

Section: Introductionmentioning

confidence: 99%

The Role of Dethreading Process in Pseudorotaxanes and Rotaxanes towards Advanced Applications: Recent Examples

Saura‐Sanmartin

2023

Eur J Org Chem

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Rotaxanes are a type of mechanically interlocked molecules (MIMs), constituted by at least a thread surrounded by a wheel, which are widely employed in the research field of artificial molecular machines. Although applications retaining the integrity of the mechanical bond are usually reported, the dethreading of the components can be crucial to develop some advanced applications. Thus, different dethreading strategies have been reported, and advanced applications which require such a process have turned out to be suitable approaches towards machine‐like operation. This review article covers recent examples of applications of pseudorotaxanes and rotaxanes in which dethreading processes have a key role to accomplish the desired function.

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Vinyl sulfonyl chemistry-driven unidirectional transport of a macrocycle through a [2]rotaxane

Abstract: By applying a combination of the coupling-and-decoupling (CAD) chemistry of the vinyl sulfonate group with the click thia-Michael addition to the vinyl sulfone group (MAVS) we performed the irreversible unidirectional...

Cited by 15 publications

References 79 publications

Curved Nanographenes as Stoppers in a [2]Rotaxane with Two-Photon Excited Emission

Curved Nanographenes as Stoppers in a [2]Rotaxane with Two-Photon Excited Emission

Molecular Ratchets and Kinetic Asymmetry: Giving Chemistry Direction

The Role of Dethreading Process in Pseudorotaxanes and Rotaxanes towards Advanced Applications: Recent Examples

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