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A Focus on Triazolium as a Multipurpose Molecular Station for pH-Sensitive Interlocked Crown-Ether-Based Molecular Machines.

Coutrot F - ChemistryOpen (2015)

Bottom Line: This can result in variations of physical or chemical properties.It also served as a molecular barrier in order to lock interlaced structures or to compartmentalize interlocked molecular machines.This review describes the recently reported examples of pH-sensitive triazolium-containing molecular machines and their peculiar features.

View Article: PubMed Central - PubMed

Affiliation: Supramolecular Machines and Architectures Team, Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 Cnrs, Faculté des Sciences, Université Montpellier, ENSCM Bâtiment Chimie (17), 3ème étage, Place Eugène Bataillon, case courrier 1706, 34095, Montpellier cedex 5, France.

ABSTRACT
The control of motion of one element with respect to others in an interlocked architecture allows for different co-conformational states of a molecule. This can result in variations of physical or chemical properties. The increase of knowledge in the field of molecular interactions led to the design, the synthesis, and the study of various systems of molecular machinery in a wide range of interlocked architectures. In this field, the discovery of new molecular stations for macrocycles is an attractive way to conceive original molecular machines. In the very recent past, the triazolium moiety proved to interact with crown ethers in interlocked molecules, so that it could be used as an ideal molecular station. It also served as a molecular barrier in order to lock interlaced structures or to compartmentalize interlocked molecular machines. This review describes the recently reported examples of pH-sensitive triazolium-containing molecular machines and their peculiar features.

No MeSH data available.


Mimicking a molecular pulley in a triply interlocked triazolium-containing rotaxane molecular machine.
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sch04: Mimicking a molecular pulley in a triply interlocked triazolium-containing rotaxane molecular machine.

Mentions: The knowledge acquired by Chen et al. on triptycene-derived crown ether hosts19 gave them the opportunity to mimic a molecular pulley (Scheme 4).[20] In their ingenious example, the triptycene moiety serves as a D3h symmetrical scaffold that bears three crown ethers. The three DB24C8 are all threaded by one single molecular axle that contains alternatively three ammonium and three N-methyltriazolium stations. In 10, the three DB24C8 derivatives encircle the ammonium stations. Deprotonation of the ammoniums triggers the forward shuttle of the cable-like thread until each DB24C8 interacts with the triazolium units. The reverse motion is possible through reprotonation of the amines using TFA. Due to the tridimensional geometry of the triptycene, the axle undergoes both translation and rotation motions, like in bi-stable [2]rotaxane and [2]catenane. The authors suggest the future incorporation of loads on either the molecular cable or on the wheel component, in analogy to the operation of a pulley.


A Focus on Triazolium as a Multipurpose Molecular Station for pH-Sensitive Interlocked Crown-Ether-Based Molecular Machines.

Coutrot F - ChemistryOpen (2015)

Mimicking a molecular pulley in a triply interlocked triazolium-containing rotaxane molecular machine.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608521&req=5

sch04: Mimicking a molecular pulley in a triply interlocked triazolium-containing rotaxane molecular machine.
Mentions: The knowledge acquired by Chen et al. on triptycene-derived crown ether hosts19 gave them the opportunity to mimic a molecular pulley (Scheme 4).[20] In their ingenious example, the triptycene moiety serves as a D3h symmetrical scaffold that bears three crown ethers. The three DB24C8 are all threaded by one single molecular axle that contains alternatively three ammonium and three N-methyltriazolium stations. In 10, the three DB24C8 derivatives encircle the ammonium stations. Deprotonation of the ammoniums triggers the forward shuttle of the cable-like thread until each DB24C8 interacts with the triazolium units. The reverse motion is possible through reprotonation of the amines using TFA. Due to the tridimensional geometry of the triptycene, the axle undergoes both translation and rotation motions, like in bi-stable [2]rotaxane and [2]catenane. The authors suggest the future incorporation of loads on either the molecular cable or on the wheel component, in analogy to the operation of a pulley.

Bottom Line: This can result in variations of physical or chemical properties.It also served as a molecular barrier in order to lock interlaced structures or to compartmentalize interlocked molecular machines.This review describes the recently reported examples of pH-sensitive triazolium-containing molecular machines and their peculiar features.

View Article: PubMed Central - PubMed

Affiliation: Supramolecular Machines and Architectures Team, Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 Cnrs, Faculté des Sciences, Université Montpellier, ENSCM Bâtiment Chimie (17), 3ème étage, Place Eugène Bataillon, case courrier 1706, 34095, Montpellier cedex 5, France.

ABSTRACT
The control of motion of one element with respect to others in an interlocked architecture allows for different co-conformational states of a molecule. This can result in variations of physical or chemical properties. The increase of knowledge in the field of molecular interactions led to the design, the synthesis, and the study of various systems of molecular machinery in a wide range of interlocked architectures. In this field, the discovery of new molecular stations for macrocycles is an attractive way to conceive original molecular machines. In the very recent past, the triazolium moiety proved to interact with crown ethers in interlocked molecules, so that it could be used as an ideal molecular station. It also served as a molecular barrier in order to lock interlaced structures or to compartmentalize interlocked molecular machines. This review describes the recently reported examples of pH-sensitive triazolium-containing molecular machines and their peculiar features.

No MeSH data available.