A two-dimensional single-layer supramolecular organic framework that is driven by viologen radical cation dimerization and further promoted by cucurbit[8]uril

Zhang, Liang; Zhou, Tian; Tian, Jia; Wang, Hui; Zhang, Dan‐Wei; Zhao, Xin; Liu, Yi; Li, Zhan‐Ting

doi:10.1039/c4py00139g

Cited by 108 publications

(76 citation statements)

References 64 publications

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“…Thus,t his band could be attributed to the Angewandte formation of the radical-cation dimer (BIPYC + ) 2 . [24] Asimilar absorption band of (BIPYC + ) 2 ,a ta round 1045 nm, was also observed for P2 ( Figure 3b). UV/Vis dilution experiments (0.8-0.1 mm)s howed that the (BIPYC + ) 2 absorption was linearly concentration-dependent (see the Supporting Information), which supports the hypothesis that the dimerization took place intramolecularly.T hus,itisreasonable to propose that the polymers incorporating BIPYC + formed another kind of pleated foldamer (Figure 2, Folded B).…”

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confidence: 53%

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

et al. 2015

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Tw od ynamic covalent polymers P1 and P2 were prepared by alternately linking electron-richtetrathiafulvalene (TTF) and electron-deficient bipyridinium (BIPY 2+ )t hrough hydrazone bonds.Inacetonitrile,the polymers were induced by intramolecular donor-acceptor interactions to form pleated foldamers,which unfolded upon oxidation of the TTF units to the radical cation TTFC + .R eduction of the BIPY 2+ units to BIPYC + led to the formation of another kind of pleated secondary structures,w hicha re stabilized by intramolecular dimerization of the BIPYC + units.T he diradical dicationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT 2( C +) ) could further force the folded structures to unfold by including the BIPYC + units of the polymers.U pon oxidation of the BIPYC + units of the cyclophane and polymers to BIPY 2+ ,t he first folded state was regenerated. Switching or conversion between the four conformational states was confirmed by UV/ Visspectroscopic experiments.

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confidence: 53%

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

et al. 2015

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“…A similar procedure applied to the star‐shaped monomer 6 led to the formation of single‐layer honeycomb‐like 2D networks whose structure was put forward on the grounds of AFM, DLS and small‐angle X‐ray diffraction data . Here again, addition of CB[8] was only found to improve the efficiency of the self‐assembly process relying on the intermolecular π‐dimerization of the chemically reduced viologen units.…”

Section: Soluble Supramolecular Assembliesmentioning

confidence: 99%

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Correia

Chowdhury

Ramos

et al. 2018

Polymer International

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This review article focuses on supramolecular assemblies involving cucurbit[n]uril‐based containers and viologen guests as key building elements. Cucurbit[n]urils (CB[n], n = 5–8,10) are fascinating hosts forming a wide range of inclusion complexes (caviplexes) with 4,4′‐bipyridinium salts, known as viologens, either as discrete 1:1 inclusion compounds with CB[7] or as ternary inclusion compounds involving two hosts or two guests (2:1 with CB[7] and 1:2 or 1:1:1 with CB[8]). This property is currently being actively exploited to design and prepare self‐assembled dynamic stimuli‐responsive supramolecular polymers including gels, vesicles, films and organized arrays of polymeric microspheres or nanoparticles. This review highlights the main benefits of such polymers and gives an overview of the achievements and progress made in this field over the past decades. © 2018 Society of Chemical Industry

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“…In contrast, far less progress has been made in these directions with electron-responsive systems, even thoughe lectrochemistry is known to be particularly attractive as at riggeri nt he perspective of applications in solid-state devices or to avoid the risks of bleaching associatedt oh igh-energyl ight irradiation. [8][9][10][11][12][13][14][15][16][17] Related to this issue, we have had al ongstandingi nterest in electron-triggered molecular or supramolecular metamorphic processes involving p-radicals as key redox-responsive elements. [18][19][20][21] Recent achievements include metal-containing tectons featuring two hetero-complementary moieties, the self-assembling ability of which could be controlled by electron transfer centered on viologens units.…”

Section: Introductionmentioning

confidence: 99%

Redox‐Induced Molecular Metamorphism Promoting a Sol/Gel Phase Transition in a Viologen‐Based Coordination Polymer

Kahlfuss

Gibaud

Denis‐Quanquin

et al. 2018

Chemistry A European J

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We have developed a strategy enabling control over the organization of ditopic molecular tectons within a palladium-based self-assembled system. The key electron-responsive sub-unit is a viologen-based mechanical hinge that can toggle under electric stimulation between a folded and a stretched position, the driving force of the folding motion being the π-dimerisation of the electrogenerated viologen cation radicals. The title ditopic tecton features two planar, N2-type, triazole/pyridine-based bidentate binding units, providing the tecton with the ability to chelate two palladium ions both in its folded and in its elongated conformations. Association of this ditopic redox-responsive tecton with palladium to form 1D self-assembled architectures undergoing large scale reorganizations in solution under electric stimulation, has been established on the ground of spectroscopic, electrochemical, spectro-electrochemical and rheological data. Our result reveal that addition of metal leads to a significant stabilization of the π-dimer species in solution and that the redox-triggered reorganisation of the tectons comes along in suitable conditions with a macroscopic sol/gel-type phase transition.

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A two-dimensional single-layer supramolecular organic framework that is driven by viologen radical cation dimerization and further promoted by cucurbit[8]uril

Abstract: Without or with the assistance of CB[8], a triangular radical monomer can self-assemble into 2D supramolecular organic frameworks in water.

Cited by 108 publications

References 64 publications

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

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

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Redox‐Induced Molecular Metamorphism Promoting a Sol/Gel Phase Transition in a Viologen‐Based Coordination Polymer

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