Switchable azo-macrocycles: from molecules to functionalisation

Li, Ziyong; Liang, Jieying; Xue, Wen; Liu, Guoxing; Liu, Sheng Hua; Yin, Jun

doi:10.1080/10610278.2013.822970

Cited by 28 publications

(11 citation statements)

References 49 publications

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“…Azobenzenes have been used for the construction of photoswitchable azo-macrocycles. 389 , 416 Azo-macrocycles have found applications in host–guest chemistry as they can selectively and reversibly bind ions. Cyclic azobenzenes have been used to switch on or off the rotation of subunits.…”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Artificial Molecular Machines

et al. 2015

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Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Artificial Molecular Machines

et al. 2015

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“…Reversible atom capture/release is well-established 33–35 . Molecules can also be imprisoned/liberated 36–44 but it is harder to achieve in a reversible all-or-none manner without complications of side-reactions 40 or incomplete conversion.…”

Section: Introductionmentioning

confidence: 99%

Molecular memory with downstream logic processing exemplified by switchable and self-indicating guest capture and release

et al. 2019

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Molecular-logic based computation (MLBC) has grown by accumulating many examples of combinational logic gates and a few sequential variants. In spite of many inspirations being available in biology, there are virtually no examples of MLBC in chemistry where sequential and combinational operations are integrated. Here we report a simple alcohol-ketone redox interconversion which switches a macrocycle between a large or small cavity, with erect aromatic walls which create a deep hydrophobic space or with collapsed walls respectively. Small aromatic guests can be captured or released in an all or none manner upon chemical command. During capture, the fluorescence of the alcohol macrocycle is quenched via fluorescent photoinduced electron transfer switching, meaning that its occupancy state is self-indicated. This represents a chemically-driven RS Flip-Flop, one of whose outputs is fed into an INHIBIT gate. Processing of outputs from memory stores is seen in the injection of packaged neurotransmitters into synaptic clefts for onward neural signalling. Overall, capture-release phenomena from discrete supermolecules now have a Boolean basis.

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“…We have made use of two o ‐xylene‐bridged bis(imidazolium)‐azobenzene motifs to impart both light‐responsiveness and receptor‐like properties to our macrocycle. In contrast to the rigid structure of more conventional azobenzene‐containing macrocycles, oAzoBox 4+ exhibits a large and flexible architecture, which has two consequences: Firstly, the photochromic properties of oAzoBox 4+ are largely unaffected in comparison to model compound, AzoBI 2+ (Figure ), by the embedment of the photoswitches in a cyclic architecture and secondly, its high flexibility is not detrimental to its recognition abilities. Therefore, oAzoBox 4+ is ideal for the realization of light‐controlled catch‐and‐release in solution.…”

Section: Figurementioning

confidence: 99%

A Dynamic and Responsive Host in Action: Light‐Controlled Molecular Encapsulation

et al. 2016

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The rational design of af lexible molecular box, oAzoBox 4+,incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E$Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components,a llowing for sequestration of small molecule guests in acetonitrile.U pon E!Zp hotoisomerization of oAzoBox 4+ the guest is expelled from the macrocyclic cavity.

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Switchable azo-macrocycles: from molecules to functionalisation

Cited by 28 publications

References 49 publications

Artificial Molecular Machines

Artificial Molecular Machines

Molecular memory with downstream logic processing exemplified by switchable and self-indicating guest capture and release

A Dynamic and Responsive Host in Action: Light‐Controlled Molecular Encapsulation

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