Light-Controlled Switching of a Non-photoresponsive Molecular Shuttle

Yang, Liu‐Pan; Jia, Fei; Cui, Jieshun; Lu, Song‐Bo; Jiang, Wei

doi:10.1021/acs.orglett.7b01184

Cited by 41 publications

(18 citation statements)

References 60 publications

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“…Figure 1 shows some typical chemical structures of stalk components employed in supramolecular nanovalves. 14,15,[22][23][24][25][26]33,[47][48][49][50][51][52][53][54] A number of supramolecular gatekeepers based on pseudorotaxanes have emerged. For instance, Hernandez and coworkers pioneered in demonstrating the earliest installation of pseudorotaxanes-based gates onto the surface of mesostructured silica for controlled release of luminescent cargos, in which 1,5-dioxynaphthalene derivatives (DNPD) acted as tethered gateposts to be further encircled by cyclobis-(paraquat-p-phenylene) (CBPQT 4+ ) rings to prepare [2]pseudorotaxanes denoted as [DNPD3CBPQT] 4+ .…”

Section: Supramolecular Pseudorotaxanes As Nanovalvesmentioning

confidence: 99%

“…[9][10][11][12][13] The environment-operable properties that could respond to external changes are realized via dynamic association and dissociation of component parts in such supramolecular assemblies. [14][15][16] Depending on the flexible modular strategy, supramolecular therapeutics directed by synthetic knowledge has been proposed, especially in the fabrication of…”

Section: Introductionmentioning

confidence: 99%

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Stimuli-Responsive Drug-Delivery Systems Based on Supramolecular Nanovalves

Song

Yang

2019

Matter

188

128

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From motor proteins to molecular machines, supramolecular chemistry has been revealed as a remarkable link to bridge the gap between biology, chemistry, and materials. Taking inspiration from the dynamic, reversible, and directional manner of non-covalent interactions that can respond to diversiform external stimuli, supramolecular nanovalves installed on the surface of inorganic or hybrid nanocarriers have received extensive attention in stimuli-responsive delivery of small drug molecules, implying their outspread bioapplications in cancer/gene therapy, biomedical application, and antimicrobial regulations. The state of supramolecular nanovalves could be well regulated by switching the conformation or the assembled/disassembled state of the assemblies. This tutorial review lays the foundation for a better understanding of the significant and typical intelligent drug-delivery systems immobilized with supramolecular polymers or supramolecular pseudorotaxanes as the gating entities of nanovalvebased molecular machines, by showing their chemical structures, operation modes, and release modalities triggered by various actuations at molecular scale. In particular, relevant perspectives of supramolecular therapeutics will also be elaborated upon.

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Section: Supramolecular Pseudorotaxanes As Nanovalvesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Stimuli-Responsive Drug-Delivery Systems Based on Supramolecular Nanovalves

Song

Yang

2019

Matter

188

128

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“…A large and reversible change of proton concentration can be induced by visible‐light irradiation using this type of photoacid. Applications of merocyanine photoacids in energy conversion, sensor, polymerization, patterning, nanomaterial, molecular machine, photochromic materials, and biomedical areas have been reported by our group and other groups.…”

Section: Introductionmentioning

confidence: 69%

Facile Synthesis and Photoactivity of Merocyanine‐Photoacid Polymers

Khalil

Alharbi

Baum

et al. 2018

Macromol. Rapid Commun.

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In recent years, merocyanine photoacids have been utilized to control various chemical processes using visible light and have found applications in materials, energy, and biomedical areas. Molecular merocyanine photoacids are commonly used in the previous works. Covalently linking the photoacids to polymers improves their compatibility with different media, avoids leakage problems, and allows a localized proton concentration to be produced. However, the phenolic and indolinium moieties of the photoacids make them difficult to be polymerized with common methods. In this work, the monomer of a merocyanine photoacid is converted to a spiropyran in situ by adding trimethylamine to a dimethyl sulfoxide (DMSO) solution of the monomer. Free radical polymerization yields the polymers of the spiropyran, which is acidified to regenerate the photoacid. The photoacid polymers prepared show good solubility, photoacidity, and reversibility. Irradiating a thin film of a photoacid polymer doped with methyl orange through a mask copies the pattern of the mask to the film. The pattern can be erased by heating the film at 80 °C for 10 min, and a new pattern is created by irradiation through a different mask.

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“… 12 Since then, PAH and structurally related compounds have been used in the context of supramolecular chemistry. Applications include the light-induced complexation of a pyridinium salt by a macrocyclic receptor, 13 the switching of a rotaxane-based molecular shuttle, 14 the light-controlled reversible self-assembly of nanorods, 15 the reversible chromism of guests in coordination cages, 16 the modulation of a hydrazine switch, 17 the reversible photo-induced gel–sol transition of a dipeptide gel, 18 and the controlled aggregation of nanoparticles, 19 among others. 11 , 20 We wanted to explore if PAH is also suited for controlling the structures of metal–ligand assemblies by light.…”

Section: Resultsmentioning

confidence: 99%