Photodriven [2]rotaxane–[2]catenane interconversion

Tron, Arnaud; Rouville, Henri Pierre Jacquot De; Ducrot, Aurélien; Tucker, James H. R.; Baroncini, Massimo; McClenaghan, Nathan D.

doi:10.1039/c4cc09472g

Cited by 26 publications

(13 citation statements)

References 38 publications

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“…Another indication of the photochemical process was the appearance of a new signal of the photoproduct at δ =79.7 ppm, corresponding to the bridgehead C 9,10 carbon for the former central anthracene ring in the 13 C NMR spectrum (Figure S5 in the Supporting Information). The resulting UV absorption spectrum of T1 after irradiation (Figure a) fully supported the formation of planar‐symmetric photoproducts that involved only the central anthracene ring and not the lateral anthracene aromatic rings, that is, there was no absorption beyond λ =300 nm . A similar conclusion can be drawn from fluorescence studies (Figure b).…”

Section: Resultssupporting

confidence: 70%

A Rare and Exclusive Endoperoxide Photoproduct Derived from a Thiacalix[4]arene Crown‐Shaped Derivative Bearing a 9,10‐Substituted Anthracene Moiety

Zhao

Tomiyasu

et al. 2016

Chemistry An Asian Journal

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A rare and exclusive endoperoxide photoproduct was quantitatively obtained from a thiacalix[4]arene crown-shaped derivative upon irradiation at λ=365 nm; the structure was unambiguously confirmed by (1) H/(13) C NMR spectroscopy and X-ray crystallography. The prerequisites for the formation of the endoperoxide photoproduct have also been discussed. Furthermore, the photochemical reaction rate could be greatly enhanced in the presence of the thiacalix[4]arene platform because it served as a host to capture oxygen.

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Section: Resultssupporting

confidence: 70%

A Rare and Exclusive Endoperoxide Photoproduct Derived from a Thiacalix[4]arene Crown‐Shaped Derivative Bearing a 9,10‐Substituted Anthracene Moiety

Zhao

Tomiyasu

et al. 2016

Chemistry An Asian Journal

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“…Light is considered as the ideal stimuli mode owing to its clean, available and wavelength variable properties. McClenaghan and co‐workers demonstrated a [2]rotaxane‐[2]catenane interconversion by the photodimerization of two terminal anthracene groups . Based on the photodimerization and the photocleavage property, coumarin and its derivatives have been used to constructed polymers and cryptand host based on crown ether .…”

Section: Methodsmentioning

confidence: 99%

Light‐Induced Cyclization of A [c2]Daisy‐Chain Rotaxane to Form a Shrinkable Double‐Lasso Macrocycle

Rao

Zhang

et al. 2018

Asian J Org Chem

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Ap H-responsive double-lasso macrocycle has been successfully obtained directly from a[ c2]daisyc hain rotaxane via ap hotodimerization reaction of two terminal coumarin ligands. The size of the double-lasso macrocycle could be tuned by acid/base stimuli with the reversible muscle-likee xtension/contraction of the [c2]daisyc hain unit.Scheme1.Synthetic route to double-lasso macrocycle 1 containing[ c2]daisy chain rotaxane. The coumarin unit formed after photodimerization has four isomerso wing to cycloaddition, and only one of them is shownh ere.

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“…Recently, we described the synthesis and characterisation of the [2]rotaxane 3 (Figure ), and studied its photochemical conversion to a well‐defined catenane product, concomitant fluorescence switching, and thermal and photochemical return to the original rotaxane structure …”

Section: Examplesmentioning

confidence: 99%

Photoactive Molecular‐Based Devices, Machines and Materials: Recent Advances

et al. 2018

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Molecular and supramolecular‐based systems and materials that can perform predetermined functions in response to light stimulation have been extensively studied in the past three decades. Their investigation continues to be a highly stimulating topic of chemical research, not only because of the inherent scientific value related to a bottom‐up approach to functional nanostructures, but also for the prospective applications in diverse fields of technology and medicine. Light is an important tool in this context, as it can be conveniently used both for supplying energy to the system and for probing its states and transformations. In this microreview we recall some basic aspects of light‐induced processes in (supra)molecular assemblies, and discuss their exploitation to implement novel functionalities with nanostructured devices, machines and materials. To this aim we illustrate a few examples from our own recent work, which are meant to illustrate the trends of current research in the field.

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Photodriven [2]rotaxane–[2]catenane interconversion

Cited by 26 publications

References 38 publications

A Rare and Exclusive Endoperoxide Photoproduct Derived from a Thiacalix[4]arene Crown‐Shaped Derivative Bearing a 9,10‐Substituted Anthracene Moiety

A Rare and Exclusive Endoperoxide Photoproduct Derived from a Thiacalix[4]arene Crown‐Shaped Derivative Bearing a 9,10‐Substituted Anthracene Moiety

Light‐Induced Cyclization of A [c2]Daisy‐Chain Rotaxane to Form a Shrinkable Double‐Lasso Macrocycle

Photoactive Molecular‐Based Devices, Machines and Materials: Recent Advances

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