Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel

Ghosh, Amit; Paul, Indrajit; Adlung, Matthias; Wickleder, Claudia; Schmittel, Michael

doi:10.1021/acs.orglett.7b03996

Cited by 65 publications

(33 citation statements)

References 46 publications

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“…Interestingly, proton exchange from 2 to 2 H + and vice versa results to be fast on NMR timescale. This finding contrasts with that obtained in the case of two previously reported molecular machines driven by fuel 1 ,H, one based on a catenane [5a] and the other on a rotaxane [5e] structure. Moreover, in the present case, the absence of any signal ascribable to the ion pair 2 H + ⋅ArC(CH 3 )CN − (state B” ) during the whole 1 H NMR monitoring of the reaction, is in accordance with a very fast back proton transfer from 2 H + to ArC(CH 3 )CN − .…”

Section: Resultscontrasting

confidence: 99%

Time Programmable Locking/Unlocking of the Calix[4]arene Scaffold by Means of Chemical Fuels

Spatola

Cacciapaglia

Casnati

et al. 2020

Chemistry A European J

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In this work,w er eport that 2-cyano-2-phenylpropanoic acid and its p-Cl, p-CH 3 and p-OCH 3 derivatives can be used as chemical fuels to control the geometry of the calix[4]arene scaffold in its cone conformation. It is shownt hat, under the action of the fuel, the cone calix[4]arenep latform assumes a" locked" shape with two opposite aromatic rings strongly convergent and the other two strongly divergent ("pinched cone" conformation). Only when the fuel is exhausted , the cone calix[4]arene scaffold returnstoi ts resting, "unlocked" shape. Remarkably,t he duration of the "locked" state can be controlled at will by varying the fuel structure or amount. Ak inetics tudy of the process shows that the consume of the fuel is catalyzed by the "unlocked"c alixarene that behaves as an autocatalyst for its own production. Am echanism is proposed fort he reaction of fuel consumption.

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Section: Resultscontrasting

confidence: 99%

Time Programmable Locking/Unlocking of the Calix[4]arene Scaffold by Means of Chemical Fuels

Spatola

Cacciapaglia

Casnati

et al. 2020

Chemistry A European J

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“…In the following, the addition of TFA initiated a second self-sorting. It was shown that the acid protonated the ligand 49, expelling zinc(II) from the complex [Zn 49 [62,63] as a chemical fuel, the protonation of 49 entailed the same cascade translocation resulting in SelfSORT-II but now with the effect that it slowly reversed back to the initial state (Figure 15b). Here, all translocations happen in an off-equilibrium system.…”

Section: Double Self-sorting (Only Structural)mentioning

confidence: 99%

Using multiple self-sorting for switching functions in discrete multicomponent systems

Ghosh¹,

Schmittel²

2020

Beilstein J. Org. Chem.

Self Cite

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Over years self-sorting has developed into a powerful tool in supramolecular chemistry, for instance, to promote the error-free formation of intricate multicomponent assemblies. However, in order to use the enormous potential of self-sorting for sophisticated information processing more recent developments have focused on the reversible reconfiguration of multicomponent systems driven by multiple self-sorting protocols. The present mini review will provide an overview over the latest advancements in this field with a focus on reversibly switchable functions in discrete supramolecular systems.

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“…We next investigated the operation of 1 under transient protonation conditions. Amongst the recently reported chemical fuels for artificial dissipative systems, the base‐catalyzed decarboxylation of carboxylic acids such as 2‐cyano‐2‐arylpropanoic acids– and trichloroacetic acid (CCl 3 CO 2 H) has the ability to temporarily switch the global pH of the reaction medium from basic to acidic for definable periods of time. Trichloroacetic acid has the additional advantage that the only waste products of the fuel are carbon dioxide and chloroform, a volatile solvent.…”

Section: Figurementioning

confidence: 99%

Dissipative Catalysis with a Molecular Machine

et al. 2019

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We report on catalysis by a fuel‐induced transient state of a synthetic molecular machine. A [2]rotaxane molecular shuttle containing secondary ammonium/amine and thiourea stations is converted between catalytically inactive and active states by pulses of a chemical fuel (trichloroacetic acid), which is itself decomposed by the machine and/or the presence of additional base. The ON‐state of the rotaxane catalyzes the reduction of a nitrostyrene by transfer hydrogenation. By varying the amount of fuel added, the lifetime of the rotaxane ON‐state can be regulated and temporal control of catalysis achieved. The system can be pulsed with chemical fuel several times in succession, with each pulse activating catalysis for a time period determined by the amount of fuel added. Dissipative catalysis by synthetic molecular machines has implications for the future design of networks that feature communication and signaling between the components.

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Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel

Cited by 65 publications

References 46 publications

Time Programmable Locking/Unlocking of the Calix[4]arene Scaffold by Means of Chemical Fuels

Time Programmable Locking/Unlocking of the Calix[4]arene Scaffold by Means of Chemical Fuels

Using multiple self-sorting for switching functions in discrete multicomponent systems

Dissipative Catalysis with a Molecular Machine

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