Quadruple Switching of Pleated Foldamers of Tetrathiafulvalene–Bipyridinium Alternating Dynamic Covalent Polymers

Chen, Lan; Wang, Hui; Zhang, Dan‐Wei; Zhou, Yaming; Li, Zhan‐Ting

doi:10.1002/ange.201410757

Cited by 4 publications

(1 citation statement)

References 75 publications

(24 reference statements)

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“…This redox-controlled actuating behavior, which has also been observed in polypyrrole 63 , 64 and polyaniline-based 65 systems—where radical chemistry also plays an important role in governing their properties—makes it possible for these viologen-based foldamers to be incorporated into polymeric materials to serve as fast-response actuators. Moreover, Li et al 66 have reported polymers whose structures are composed of alternating TTF and BIPY 2+ units. By switching on and off the radical-pairing interactions between BIPY •+ units through redox chemistry, these polymers can change their folding conformations reversibly between two states.…”

Section: Multistimulus-responsive Materialsmentioning

confidence: 99%

Introducing Stable Radicals into Molecular Machines

2017

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Ever since their discovery, stable organic radicals have received considerable attention from chemists because of their unique optical, electronic, and magnetic properties. Currently, one of the most appealing challenges for the chemical community is to develop sophisticated artificial molecular machines that can do work by consuming external energy, after the manner of motor proteins. In this context, radical-pairing interactions are important in addressing the challenge: they not only provide supramolecular assistance in the synthesis of molecular machines but also open the door to developing multifunctional systems relying on the various properties of the radical species. In this Outlook, by taking the radical cationic state of 1,1′-dialkyl-4,4′-bipyridinium (BIPY•+) as an example, we highlight our research on the art and science of introducing radical-pairing interactions into functional systems, from prototypical molecular switches to complex molecular machines, followed by a discussion of the (i) limitations of the current systems and (ii) future research directions for designing BIPY•+-based molecular machines with useful functions.

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Section: Multistimulus-responsive Materialsmentioning

confidence: 99%

Introducing Stable Radicals into Molecular Machines

2017

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Bipyridinium Polymers That Dock Tetrathiafulvalene Guests in Water Driven by Donor–Acceptor and Ion Pair Interactions

Zhang

Qin

Wang

et al. 2016

Chemistry An Asian Journal

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Two water-soluble para-xylylene-connected 4,4'-bipyridinium (BIPY(2+) ) polymers have been prepared. UV-Vis absorption, (1) H NMR spectroscopy, and cyclic voltammetry experiments support that in water the BIPY(2+) units in the polymers form stable 1:1 charge-transfer complexes with tetrathiafulvalene (TTF) guests that bear two or four carboxylate groups. These charge-transfer complexes are stabilized by the donor-acceptor interaction between electron-rich TTF and electron-deficient BIPY(2+) units and electrostatic attraction between the dicationic BIPY(2+) units and the anionic carboxylate groups attached to the TTF core. On the basis of UV-Vis experiments, a lower limit to the apparent association constant of the TTF⋅BIPY(2+) complexes of the mixtures, 1.8×10(6) m(-1) , has been estimated in water. Control experiments reveal substantially reduced binding ability of the neutral TTF di- and tetracarboxylic acids to the BIPY(2+) molecules and polymers. Moreover, the stability of the charge-transfer complexes formed by the BIPY(2+) units of the polymers are considerably higher than that of the complexes formed between two monomeric BIPY(2+) controls and the dicarboxylate-TTF donor; this has been attributed to the mutually strengthened electron-deficient nature of the BIPY(2+) units of the polymers due to the electron-withdrawing effect of the BIPY(2+) units.

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Dynamic Molecular Metamorphism Involving Palladium‐Assisted Dimerization of π‐Cation Radicals

Kahlfuss

Grüber

Dumont

et al. 2019

Chemistry A European J

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A dynamic supramolecular approach is developed to promote the π‐dimerization of viologen radicals at room temperature and in standard concentration ranges. The approach involves cis‐ or trans‐protected palladium centers serving as inorganic hinges linking two functionalized viologens endowed with metal‐ion coordinating properties. Based on detailed spectroscopic, electrochemical and computational data, we show that the one‐electron electrochemical reduction of the viologen units in different dynamic metal/ligand mixtures leads to the formation of the same intramolecular π‐dimer, regardless of the initial environment around the metallic precursor and of the relative ratio between metal and ligand initially introduced in solution. The large‐scale electron‐triggered reorganization of the building blocks introduced in solution thus involves drastic changes in the stoichiometry and stereochemistry of the palladium/viologen complexes proceeding in some cases through a palladium centered trans→cis isomerization of the coordinated ligands.

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Quadruple Switching of Pleated Foldamers of Tetrathiafulvalene–Bipyridinium Alternating Dynamic Covalent Polymers

Cited by 4 publications

References 75 publications

Introducing Stable Radicals into Molecular Machines

Introducing Stable Radicals into Molecular Machines

Bipyridinium Polymers That Dock Tetrathiafulvalene Guests in Water Driven by Donor–Acceptor and Ion Pair Interactions

Dynamic Molecular Metamorphism Involving Palladium‐Assisted Dimerization of π‐Cation Radicals

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