The construction of single-layer two-dimensional supramolecular organic frameworks in water through the self-assembly of rigid vertexes and flexible edges

Zhang, Xiang; Nie, Cheng-Bin; Zhou, Tian; Qi, Qiao-Yan; Fu, Jie; Wang, Xiaozhong; Dai, Liyan; Chen, Yingqi; Zhao, Xin

doi:10.1039/c4py01669f

Cited by 50 publications

(31 citation statements)

References 38 publications

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“…After the formationo ft he 2D SOF by mixingT PE-4MV, CB [8],a nd AZO at am olar ratio of 1:4:2i nw ater was confirmed, the properties of the SOF were explored by various testingm ethods including dynamic light scattering (DLS), small-angle X-ray scattering (SAXD), atomic force microscopy (AFM), and scanning electronm icroscopy (SEM).D LS results ( Figure 2c)s howed that the hydrodynamic diameter (D H )o f AZO and TPE-4MV was 0.63 and 1.29 nm, respectively.W hen CB [8] was added,t he D H of the complex increased rapidly to 190 nm, indicating that the organic monomers formed large assemblies in water.I na ddition, as cattering peak with d spacing of approximately 5.53 nm was clearly noticed in the SAXD profile ( Figure 2d), suggesting the periodicity of the interior of the assemblies. [40] All theser esults confirmed the SOF formation. In addition, the morphology of the SOF wasi nvestigated by SEM ( Figure 3a)a nd AFM ( Figure 3b).…”

Section: Resultssupporting

confidence: 54%

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Zhang

Liang

Yang

2019

Chemistry A European J

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A 2D supramolecular organic framework (SOF) based on synthetic macrocycles has been constructed in water by a self‐assembly strategy. Two new organic monomers of this SOF, possessing viologen and azobenzene functional groups, form a stimuli‐responsive host–guest system upon cooperatively binding with cucurbit[8]uril rings. The reversible formation and dissociation of 2D SOF can be realized by the isomerization of azobenzene under ultraviolet and visible light. The light‐responsive property of the SOF is highly reversible and stable for up to four cycles. Moreover, azoreductase produced by Escherichia coli can reduce the N=N double bond of azobenzene entities, resulting in fluorescence recovery of the system. As an excellent and effective fluorescent probe, the SOF can detect azoreductase activity for real‐time monitoring of the growth process of Escherichia coli. The dual‐stimuli responsive 2D SOF is envisioned to drive the development of responsive devices with complex functions.

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Section: Resultssupporting

confidence: 54%

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Zhang

Liang

Yang

2019

Chemistry A European J

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“…The multi-step synthesis of the key tetratopic tecton, namely the tetra(mesoviologen)porphyrins 1M 8+ (M = H2 or Zn), is summarized in Figure 2. This synthesis is actually the result of an improvement of a previously reported procedure [40]. The starting point is a standard Rothemund condensation of pyrrole with 4-nitrobenzaldehyde in a propionic acid/acetic anhydride mixture yielding the corresponding 5,10,15,20-tetrakis(4'nitrophenyl)porphyrin 4H2 in 30% yield.…”

Section: Synthesismentioning

confidence: 97%

Photo/redox-responsive 2D-Supramolecular assembly involving Cucurbit[8]uril and a star-shaped porphyrin tecton

Chowdhury

Nassar

Guy

et al. 2019

Electrochimica Acta

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The present paper reports on the formation and on the electrochemical/spectroscopic characterization of inclusion complexes formed in aqueous media between cucurbit[7 or 8]urils cavitands (CB[7], CB[8]) and a rigid four-pointed star-shaped viologen-appended porphyrin tecton. The formation of discrete 4:1 pseudo-rotaxane-like caviplexes, involving threading of CB[n] rings on the rigid viologen-based star's branches has been demonstrated by nuclear magnetic resonance and mass spectrometry measurements. Then, the photo-and redoxtriggered formation of 2D supramolecular assemblies involving CB[8]s and the four electron reduced tectons as key building elements, has been established on the ground of in-depth electrochemical and spectroscopic analyses supported by quantum calculations. The CB[8]promoted intermolecular -dimerization of the viologen cation radicals introduced at the meso positions of the porphyrin plateform has been brought to light through the diagnostic signatures of the 1:2 host-guest ternary caviplexes formed between viologen and CB[8] and by spectroscopic data collected after electrochemical, chemical or photochemical reduction of the viologen-based tectons. The CB[8] hosts not only proved useful to promote the redox-triggeredformation of supramolecular assemblies, it was also found to prevent the chemical reduction of the porphyrin ring in aqueous media and its subsequent conversion into phlorin products.

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“…Nevertheless, it is astounding to find thus far only a few reports on the formation of 2D SOFs, which all failed to demonstrate a long-range internal order. 22−24 To the best of our knowledge, all previous 2D SOFs were prepared in aqueous media, where they suffered from small domain sizes and low processability. Moreover, the preparation of free-standing 2D SOFs without substrate supports remains elusive, although it is imperative for their applications as membranes, for example, in ultrasensitive pressure sensors and size excluding films.…”

Section: Introductionmentioning

confidence: 99%

“…1,4,28 This is presumably due to the intrinsic defects or a limited strength of supramolecular interactions, which cannot solely sustain the SOF structures, leading to fragility. 22−24 …”

Section: Introductionmentioning

confidence: 99%

Free-Standing Monolayer Two-Dimensional Supramolecular Organic Framework with Good Internal Order

et al. 2015

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Utilizing dynamic self-assembly and self-sorting to obtain large-area, molecularly precise monolayered structures represents a promising approach toward two-dimensional supramolecular organic frameworks (2D SOF) or 2D supramolecular polymers. So far, related approaches suffer from small domain sizes, fragility and weak long-range internal order. Here we report on the self-assembly of a host–guest enhanced donor–acceptor interaction, consisting of a tris(methoxynaphthyl)-substituted truxene spacer, and a naphthalene diimide substituted with N-methyl viologenyl moieties as donor and acceptor monomers, respectively, in combination with cucurbit[8]uril as host monomer toward monolayers of an unprecedented 2D SOF. Featuring orthogonal solubility, the participating molecules self-assemble at a liquid–liquid interface, yielding exceptionally large-area, insoluble films, which were analyzed by transmission electron microscopy, atomic force microscopy and optical microscopy to be monolayers with a thickness of 1.8 nm, homogeneously covering areas up to 0.25 cm2, and featuring the ability to be free-standing over holes of 10 μm2. Characterization with ultraviolet–visible absorption spectroscopy, solid-state nuclear magnetic resonance spectroscopy, infrared spectroscopy, and grazing incidence wide-angle X-ray scattering allowed for confirmation of a successful complexation of all three monomers toward an internal long-range order and gave indications to an expected hexagonal superstructure. Our results extend the existing variety of two-dimensional soft nanomaterials by a versatile supramolecular approach, whereas the possibility of varying the functional monomers is supposed to open adaptability to different applications like membranes, sensors, molecular sieves, and optoelectronics.

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The construction of single-layer two-dimensional supramolecular organic frameworks in water through the self-assembly of rigid vertexes and flexible edges

Abstract: Single-layer two-dimensional supramolecular organic frameworks were constructed through self-assembly of rigid vertexes, flexible edges, and cucurbit[8]uril hosts.

Cited by 50 publications

References 38 publications

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Dual‐Stimuli Responsive 2D Supramolecular Organic Framework for the Detection of Azoreductase Activity

Photo/redox-responsive 2D-Supramolecular assembly involving Cucurbit[8]uril and a star-shaped porphyrin tecton

Free-Standing Monolayer Two-Dimensional Supramolecular Organic Framework with Good Internal Order

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