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Probing rotaxane dynamics with F NMR/MRI: Unveiling the roles of mechanical bond and steric hindrance.
Anal Chim Acta
August 2024
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan, Wuhan Institute of Physics and Mathematics, Innovation Academy for Precision Measurement Science and Technology, Chinese Academy of Sciences-Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan, 430071, China; University of Chinese Academy of Sciences, Beijing, 100049, China.
Background: Deciphering the molecular dynamics (MD) of rotaxanes is crucial for designing and refining their applications in molecular devices. This study employed fluorine-19 nuclear magnetic resonance (F NMR) and magnetic resonance imaging (MRI) to unveil the interplay between mechanical bonds and steric hindrance in a series of fluorinated rotaxanes.
Results: H/F NMR revealed stable "Z"-shaped wheel conformations minimizing steric clashes and favoring π-π interactions with the axle.
Light-responsive rotaxane-based materials: inducing motion in the solid state.
Beilstein J Org Chem
June 2023
Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, 30100 Murcia, Spain.
Light-responsive rotaxane-based solid-state materials are ideal scaffolds in order to develop smart materials due to the properties provided by the mechanical bond, such as control over the dynamics of the components upon application of external stimuli. This perspective aims to highlight the relevance of these materials, by pointing out recent examples of photoresponsive materials prepared from a rotaxanated architecture in which motion of the counterparts and/or macroscopic motion of the interlocked materials are achieved. Although further development is needed, these materials are envisioned as privileged scaffolds which will be used for different advanced applications in the area of molecular machinery.
View Article and Find Full Text PDFAsymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers.
Commun Chem
June 2023
University of Zurich, Department of Chemistry, Winterthurerstrasse 190, CH-8057, Zurich, Switzerland.
Dual-modality imaging agents featuring both a radioactive complex for positron emission tomography (PET) and a fluorophore for optical fluorescence imaging (OFI) are crucial tools for reinforcing clinical diagnosis and intraoperative surgeries. We report the synthesis and characterisation of bimodal mechanically interlocked rotaxane-based imaging agents, constructed via the cucurbit[6]uril CB[6]-mediated alkyne-azide 'click' reaction. Two synthetic routes involving four- or six-component reactions are developed to access asymmetric rotaxanes.
View Article and Find Full Text PDFForce-Induced Shuttling of Rotaxanes Controls Fluorescence Resonance Energy Transfer in Polymer Hydrogels.
ACS Appl Mater Interfaces
February 2023
Department of Materials Science and Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan.
The molecular shuttling function of rotaxanes can be exploited to design mechanoresponsive reporter molecules. Here, we report a new approach to such rotaxane-based mechanophores, in which the fluorescence resonance energy transfer (FRET) between a donor-acceptor pair is mechanically controlled. A cyclic molecule containing a green-light-emitting FRET donor connected to a red-light-emitting FRET acceptor was threaded onto an axle equipped with a quencher at its center and two stoppers in the peripheral positions.
View Article and Find Full Text PDFEffect of Charge State on the Equilibrium and Kinetic Properties of Mechanically Interlocked [5]Rotaxane: A Molecular Dynamics Study.
J Phys Chem B
February 2023
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara06800, Turkey.
Rotaxanes can exhibit stimuli-responsive behavior by allowing positional fluctuations of their rota groups in response to physiochemical conditions such as the changes in solution pH. However, ionic strength of the solution also affects the molecular conformation by altering the charge state of the entire molecule, coupling the stimuli-responsiveness of rotaxanes with their conformation. A molecular-scale investigation on a model system can allow the decoupling and identification of various effects and can greatly benefit applications of such molecular switches.
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