Formation of a pseudorotaxane, capable of sensing cations via dethreading molecular motion, from a cryptand and bipyridinium salts

Muraoka, Masahiro; Ohta, Mamoru; Mizutani, Yuko; Takezawa, Mashio; Matsumoto, Ayuri; Nakatsuji, Yohji

doi:10.1007/s10847-012-0280-z

Cited by 3 publications

(2 citation statements)

References 62 publications

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“…Similarly, Beer et al reported analogous results for the cobaltocenium (Cc + ) derivative 14. 146 Concerning the use of the capping strategy for the development of allosterically regulated hosts, Muraoka et al designed the cryptand 15, 147 having two different crown ether moieties merged: a primary binding site having electron-rich HQ moieties for the complexation of paraquat, and a secondary allosteric site for the complexation of Na + (Scheme 13). The binding of the organic substrate is regulated by the alkali cation, which causes the expulsion of the organic guest from the primary site because of the appearance of electrostatic repulsions.…”

Section: Capping Of Macrocyclic Hosts With Molecular Switchesmentioning

confidence: 99%

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Controlled binding of organic guests by stimuli-responsive macrocycles

et al. 2020

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Section: Capping Of Macrocyclic Hosts With Molecular Switchesmentioning

confidence: 99%

“…Examples of allosteric SSs based on the capping strategy. [147][148][149][150] Finally, in an interesting example of synergy between coordination and host-guest chemistry, Mirkin et al have developed the coordination-controlled switchable calixarene 18 (Scheme 13). 150 In this compound, a CX [4] 4.…”

Section: Capping Of Macrocyclic Hosts With Molecular Switchesmentioning

confidence: 99%

Controlled binding of organic guests by stimuli-responsive macrocycles

et al. 2020

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Template-Free Synthesis of a Phenanthroline-Containing [2]Rotaxane: A Reversible pH-Controllable Molecular Switch

et al. 2019

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The synthesis of symmetric and asymmetric rotaxanes consisting of neutral axle and ring components without ionic templates is necessary for applications in molecular sensors and molecular switches. A phenanthroline-containing symmetric [2]rotaxane was newly synthesized by inducing hydrogen bonding and π-interaction using a template-free threading-followed-by-stoppering method. The obtained rotaxane serves as a reversible pH-controllable molecular switch.

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Synthesis and Properties of Stimuli-Responsive Pseudorotaxanes

Muraoka

2013

Oleoscience

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Abstract:Various mechanically interlocked molecules such as rotaxanes and catenanes have been prepared toward future realization of molecular machines. Moreover, intense recent research interest has been focused on technological applications of rotaxanes and catenanes as a molecular sensor and a catalyst.A macrocycle having a bisamide and a half dibenzo-crown ether component was newly synthesized and its complexation behavior toward neutral phenanthroline derivatives is reported. The macrocycle can bind phenanthroline derivatives very strongly through the hydrogen bonding and π-electron interactions, yielding pseudorotaxane structures. The inclusion complexes show a pH-controllable reversible threading-dethreading molecular switching property.A new type of cryptand-based pseudorotaxane was prepared, utilizing a novel cryptand incorporating two aromatic rings as a wheel component, combined with various bipyridinium salts as the axle component. These pseudorotaxanes exhibited charge-transfer absorption at approximately 380 nm due to π-electron interactions between the cryptand and the bipyridinium salt. Upon addition of one equivalent of sodium ion to the pseudorotaxane, this absorption was disappeared as a result of displacement of the bipyridinium salt by the sodium.

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Formation of a pseudorotaxane, capable of sensing cations via dethreading molecular motion, from a cryptand and bipyridinium salts

Cited by 3 publications

References 62 publications

Controlled binding of organic guests by stimuli-responsive macrocycles

Controlled binding of organic guests by stimuli-responsive macrocycles

Template-Free Synthesis of a Phenanthroline-Containing [2]Rotaxane: A Reversible pH-Controllable Molecular Switch

Synthesis and Properties of Stimuli-Responsive Pseudorotaxanes

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