Shape‐Controllable and Fluorescent Supramolecular Organic Frameworks Through Aqueous Host–Guest Complexation

Li, Yawen; Dong, Yunhui; Miao, Xiaran; Ren, Yulin; Zhang, Beilin; Wang, Pinpin; Yang, Yu; Li, Bin; Isaacs, Lyle; Cao, Liping

doi:10.1002/anie.201710553

Cited by 169 publications

(92 citation statements)

References 34 publications

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“…CBn can be employed in numerous applications that are based on the extraordinary high affinity displayed by these macrocycles. Examples include recognition, self‐assembly and isolation of biomolecules, noncovalent functionalization of biopharmaceuticals, bioimaging and supramolecular materials such as polymers, microcapsules, and supramolecular organic frameworks …”

Section: Methodsmentioning

confidence: 99%

“…Examples include recognition, self-assembly andi solationo fb iomolecules, noncovalent functionalization of biopharmaceuticals, bioimaging and supramolecular materials such as polymers, microcapsules, and supramolecular organic frameworks. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] Akey feature of supramolecular systems relies on the reversible nature of noncovalent bonds,a llowing control of association processes using externals timuli. Light is recognized as a superior stimulusf or many applications because it allows for remote spatiotemporal control, it is orthogonal to other stimuli, and additional reagents are not required.…”

mentioning

confidence: 99%

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A Visible–Near‐Infrared Light‐Responsive Host–Guest Pair with Nanomolar Affinity in Water

Ferreira

Ventura

Barbieri

et al. 2019

Chemistry A European J

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The discovery of stimuli‐responsive high affinity host–guest pairs with potential applications under biologically relevant conditions is a challenging goal. This work reports a high‐affinity 1:1 complex formed between cucurbit[8]uril and a water‐soluble photochromic diarylethene derivative. It was found that, by confining the open isomer within the cavity of the receptor, a redshift in the absorption spectrum and an enhancement of the photocyclization quantum yield from Φ=0.04 to Φ=0.32 were induced. This improvement in the photochemical performance enables quantitative photocyclization with visible light that, together with the near‐infrared light‐induced ring‐opening reaction and the 100‐fold selectivity for the closed isomer, confirms this as an outstanding light‐responsive affinity pair.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

A Visible–Near‐Infrared Light‐Responsive Host–Guest Pair with Nanomolar Affinity in Water

Ferreira

Ventura

Barbieri

et al. 2019

Chemistry A European J

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“…Supramolecular self-assemblies with fluorescence for cell imaging have attracted raising attention of chemists in recent years, [1] especially for organelle-targeted cell imaging.Among various organelles in cells,lysosome is an important organelle that is involved in various cell processes,i ncluding degradation of polymers,s ecretion, plasma membrane repair, cell signaling,a nd energy metabolism. [2] Several lysosome-targeted probes have been reported based on rhodamine [3] and ruthenium complexes.…”

Section: Supramolecular Assemblieswith Near-infrared Emission Mediatementioning

confidence: 99%

Supramolecular Assemblies with Near‐Infrared Emission Mediated in Two Stages by Cucurbituril and Amphiphilic Calixarene for Lysosome‐Targeted Cell Imaging

et al. 2018

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A two-stage mediated near-infrared (NIR) emissive supramolecular assembly for lysosome-targeted cell imaging is presented. 4,4'-Anthracene-9,10-diylbis(ethene-2,1-diyl))bis(1-ethylpyridin-1-ium) bromide (ENDT) was synthesized as an organic dye with weak fluorescence emission at 625 nm. When ENDT complexes with cucurbit[8]uril (CB[8]), this binary supramolecular complex assembles into nanorods with a near-infrared fluorescence emission (655 nm) and fluorescence enhancement as the first stage. Such supramolecular complexes interact with lower-rim dodecyl-modified sulfonatocalix[4]arene (SC4AD) to form nanoparticles for further fluorescence enhancement as the second stage. Furthermore, based on a co-staining experiment with LysoTracker Blue, such nanoparticles can be applied in NIR lysosome-targeted cell imaging.

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“…Br − counterions omitted for clarity. affinity (ΔG < −13.6 kcal/mol, K > 10 10 M −2 ); 32 both homoternary and heteroternary interactions have been widely used as the driving force for fabrication of various aqueous supramolecular systems including supramolecular oligomers 33−35 and polymers, 36−43 supramolecular hydrogels, 44−47 supramolecular organic frameworks, 48,49 protein/ peptide self-assemblies, 50,51 and functional interfaces. 52−54 Therefore, we posited that CB [8] could enhance phenylperfluorophenyl polar−π interactions.…”

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confidence: 99%

Host-Enhanced Phenyl-Perfluorophenyl Polar−π Interactions

Huang

Chen

et al. 2020

J. Am. Chem. Soc.

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Phenyl-perfluorophenyl polar−π interactions have been revisited for the design and fabrication of functional supramolecular systems. The relatively weak associative interactions (ΔG ≈ −1.0 kcal/mol) have limited their use in aqueous selfassembly to date. Herein, we propose a strategy to strengthen phenyl-perfluorophenyl polar−π interactions by encapsulation within a synthetic host, thus increasing the binding affinity to ΔG= −15.5 kcal/mol upon formation of heteroternary complexes through social self-sorting. These heteroternary complexes were used as dynamic, yet strong, cross-linkers in the fabrication of supramolecular gels, which exhibited excellent viscoelasticity, stretchability, self-recovery, self-healing, and energy dissipation. This work unveils a general approach to exploit host-enhanced polar−π interactions in the design of robust aqueous supramolecular systems.

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Shape‐Controllable and Fluorescent Supramolecular Organic Frameworks Through Aqueous Host–Guest Complexation

Cited by 169 publications

References 34 publications

A Visible–Near‐Infrared Light‐Responsive Host–Guest Pair with Nanomolar Affinity in Water

A Visible–Near‐Infrared Light‐Responsive Host–Guest Pair with Nanomolar Affinity in Water

Supramolecular Assemblies with Near‐Infrared Emission Mediated in Two Stages by Cucurbituril and Amphiphilic Calixarene for Lysosome‐Targeted Cell Imaging

Host-Enhanced Phenyl-Perfluorophenyl Polar−π Interactions

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