Limits...
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.


Related in: MedlinePlus

An ammonium/triazolium-containing pH-sensitive molecular muscle. Reagents and conditions: a) 1) mannosyl azide (pictured), Cu(CH3CN)4PF6, lutidine, 2) CH3I then NH4PF6; b) NaOH (aq)/CH2Cl2; c) 1) HCl/Et2O, 2) NH4PF6.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4608521&req=5

sch14: An ammonium/triazolium-containing pH-sensitive molecular muscle. Reagents and conditions: a) 1) mannosyl azide (pictured), Cu(CH3CN)4PF6, lutidine, 2) CH3I then NH4PF6; b) NaOH (aq)/CH2Cl2; c) 1) HCl/Et2O, 2) NH4PF6.

Mentions: “Molecular muscle”35 is a generic term used for a molecule designed to adopt a contracted or a stretched co-conformation in response to a stimulus, in a similar manner to human muscles. Inspired by the pioneering work of Jean-Pierre Sauvage36 on doubly interlocked molecular architectures and by those of Fraser Stoddart on DB24C8-based [c2]daisy chain,37 we reported in 2008 the first pH-sensitive molecular muscle. A few other examples based on other systems have been reported since then.38 We actually extended the ammonium–triazolium system of recognition sites for DB24C8 that we previously published13 in the [2]rotaxane series to the preparation of a dimannosyl pH-sensitive molecular muscle (Scheme 14).39


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

Coutrot F - ChemistryOpen (2015)

An ammonium/triazolium-containing pH-sensitive molecular muscle. Reagents and conditions: a) 1) mannosyl azide (pictured), Cu(CH3CN)4PF6, lutidine, 2) CH3I then NH4PF6; b) NaOH (aq)/CH2Cl2; c) 1) HCl/Et2O, 2) NH4PF6.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

sch14: An ammonium/triazolium-containing pH-sensitive molecular muscle. Reagents and conditions: a) 1) mannosyl azide (pictured), Cu(CH3CN)4PF6, lutidine, 2) CH3I then NH4PF6; b) NaOH (aq)/CH2Cl2; c) 1) HCl/Et2O, 2) NH4PF6.
Mentions: “Molecular muscle”35 is a generic term used for a molecule designed to adopt a contracted or a stretched co-conformation in response to a stimulus, in a similar manner to human muscles. Inspired by the pioneering work of Jean-Pierre Sauvage36 on doubly interlocked molecular architectures and by those of Fraser Stoddart on DB24C8-based [c2]daisy chain,37 we reported in 2008 the first pH-sensitive molecular muscle. A few other examples based on other systems have been reported since then.38 We actually extended the ammonium–triazolium system of recognition sites for DB24C8 that we previously published13 in the [2]rotaxane series to the preparation of a dimannosyl pH-sensitive molecular muscle (Scheme 14).39

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.


Related in: MedlinePlus