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Open AccessJournal ArticleDOI

The importance of the rotor in hydrazone-based molecular switches

TLDR
The pH-activated E/Z isomerization of a series of hydrazone-based systems having different functional groups as part of the rotor was studied and it was found that the nature of the R group is critical for efficient switching to occur.
Abstract
The pH-activated E/Z isomerization of a series of hydrazone-based systems having different functional groups as part of the rotor (R = COMe, CN, Me, H), was studied. The switching efficiency of these systems was compared to that of a hydrazone-based molecular switch (R = COOEt) whose E/Z isomerization is fully reversible. It was found that the nature of the R group is critical for efficient switching to occur; the R group should be a moderate H-bond acceptor in order to (i) provide enough driving force for the rotor to move upon protonation, and (ii) stabilize the obtained Z configuration, to achieve full conversion.

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Citations
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Journal ArticleDOI

Artificial Molecular Machines

TL;DR: The latest generations of sophisticated synthetic molecular machine systems in which the controlled motion of subcomponents is used to perform complex tasks are discussed, paving the way to applications and the realization of a new era of “molecular nanotechnology”.
Journal ArticleDOI

Hydrazone-based switches, metallo-assemblies and sensors

TL;DR: An overview of the utilization of hydrazones in three supramolecular chemistry related areas: molecular switches, metallo-assemblies and sensors is provided.
Journal ArticleDOI

Visible light switching of a BF2-coordinated azo compound.

TL;DR: Theoretical calculations indicate that the absorption bands in the visible range can be tuned using different Lewis acids, opening the way to a conceptually new strategy for the manipulation of azo compounds using only visible light.
Journal ArticleDOI

Simple hydrazone building blocks for complicated functional materials.

TL;DR: This Account will describe how the quest to design new molecular switches has led to the development of structurally simple systems that can be used for complicated functions, and demonstrates that the approach of developing simple systems for sophisticated functions is not limited to the field of molecular switches and machines but can also encompass other adaptive materials.
Journal ArticleDOI

Shape-Persistent Actuators from Hydrazone Photoswitches

TL;DR: It is demonstrated that bistable hydrazones can drive (chiral) shape transformations in liquid crystal polymer networks, with photogenerated polymer shapes displaying a long-term stability that mirrors that of the switches.
References
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Journal ArticleDOI

A Molecular Elevator

TL;DR: This molecular elevator is considerably more complex and better organized than previously reported artificial molecular machines and exhibits a clear-cut on-off reversible behavior, and it could develop forces up to around 200 piconewtons.
Journal ArticleDOI

Photoswitches: From Molecules to Materials

TL;DR: Moving from supramolecular systems in solution to surfaces and finally to bulk materials, important design concepts are discussed, emphasizing both the challenges as well as the great promise of such truly advanced materials.
Journal ArticleDOI

Unidirectional rotation in a mechanically interlocked molecular rotor.

TL;DR: It is shown that sequential and unidirectional rotation can also be induced in mechanically interlocked assemblies comprised of one or two small rings moving around one larger ring.
Journal ArticleDOI

Molecular machines: nanomotor rotates microscale objects.

TL;DR: A synthetic, light-driven molecular motor that is embedded in a liquid-crystal film and can rotate objects placed on the film that exceed the size of the motor molecule by a factor of 10,000.
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