Cation-Modulated Rotary Speed in a Light-Driven Crown Ether Functionalized Molecular Motor

Dorel, Ruth; Miro, C; Wei, Yu‐Chen; Wezenberg, Sander J.; Feringa, Ben L.

doi:10.1021/acs.orglett.8b00969

Cited by 20 publications

(16 citation statements)

References 43 publications

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“…Thus, the binding of a viologen guest can influence both the thermal and photochemical properties of the conjugate systems. In this context, it is of interest to mention that host–guest interactions in crown-ether functionalized second-generation light-driven molecular motors have been used to modulate the properties of the molecular motor moiety 35 .…”

Section: Resultsmentioning

confidence: 99%

Molecular motor-functionalized porphyrin macrocycles

et al. 2020

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Molecular motors and switches change conformation under the influence of an external stimulus, e.g. light. They can be incorporated into functional systems, allowing the construction of adaptive materials and switchable catalysts. Here, we present two molecular motor-functionalized porphyrin macrocycles for future photo-switchable catalysis. They display helical, planar and point chirality, and are diastereomers, which differ in the relative orientation of the motor and macrocyclic components. Fluorescence, UV-vis, and 1H NMR experiments reveal that the motor-functionalized macrocycles can bind and thread different variants of viologen guests, including a one-side blocked polymeric one of 30 repeat units. The latter feature indicates that the motor systems can find the open end of a polymer chain, thread on it, and move along the chain to eventually bind at the viologen trap, opening possibilities for catalytic writing on single polymer chains via chemical routes.

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Section: Resultsmentioning

confidence: 99%

Molecular motor-functionalized porphyrin macrocycles

et al. 2020

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“…The binding affinity of the amine guest can be tuned by the addition of either methanol or acetic acid, thus allowing the behavior of the molecular motor to be reversibly modulated through a combination of different chemical triggers. Along the same direction, by functionalization of the motor with a crown ether moiety, the rotary speed could be modulated by complexation with different metal cations . More recently, in second-generation motor 33 bearing a photochromic dithienylethene (DTE) moiety attached to its rotor portion (Figure b), the possibility of light-gating of the rotational motion was demonstrated .…”

Section: Photochemically Driven Motorsmentioning

confidence: 98%

Photo- and Redox-Driven Artificial Molecular Motors

2019

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Directed motion at the nanoscale is a central attribute of life, and chemically driven motor proteins are nature’s choice to accomplish it. Motivated and inspired by such bionanodevices, in the past few decades chemists have developed artificial prototypes of molecular motors, namely, multicomponent synthetic species that exhibit directionally controlled, stimuli-induced movements of their parts. In this context, photonic and redox stimuli represent highly appealing modes of activation, particularly from a technological viewpoint. Here we describe the evolution of the field of photo- and redox-driven artificial molecular motors, and we provide a comprehensive review of the work published in the past 5 years. After an analysis of the general principles that govern controlled and directed movement at the molecular scale, we describe the fundamental photochemical and redox processes that can enable its realization. The main classes of light- and redox-driven molecular motors are illustrated, with a particular focus on recent designs, and a thorough description of the functions performed by these kinds of devices according to literature reports is presented. Limitations, challenges, and future perspectives of the field are critically discussed.

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“…Modulation of the speed of rotation was recently achieved by Feringa through metal coordination . The attachment of a crown-ether moiety at the stator part of the overcrowded alkene 68 allowed the addition of a cation to regulate the rotational rate (Scheme a).…”

Section: Motion Related Functionsmentioning

confidence: 99%

(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

et al. 2019

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A look at the elegance and efficiency of biological machines readily reveals that Nature masters the full gamut of chemical interactions to compose masterpieces of the living world. The present analysis singles out metal coordination for the actuation of nanomechanical motion. According to our analysis, metal coordination has a manifold of rewards, putting it primo loco in opportunities for putting nanomechanical systems into action: (i) its strength and dynamics can be properly modulated and fine-tuned by the choice of metal, redox state, and ligand(s), (ii) the high directionality of the interaction allows reliable design, and (iii) the emergence of novel self-sorting algorithms allows multiple of these interactions to be working in parallel. On top of all these advantages, intermolecular metal-ion translocation is a well-known factor in biological signaling. These benefits have recently proven their usefulness in the operation of networked devices and in overcoming the limitations of traditional stand-alone molecular systems.

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Cation-Modulated Rotary Speed in a Light-Driven Crown Ether Functionalized Molecular Motor

Cited by 20 publications

References 43 publications

Molecular motor-functionalized porphyrin macrocycles

Molecular motor-functionalized porphyrin macrocycles

Photo- and Redox-Driven Artificial Molecular Motors

(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

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