An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

Zheng, Anxun; Gong, Cheng-Bin; Zhang, Wei-Jing; Tang, Qian; Huang, Hairong; Chow, Cheuk Fai Stephen

doi:10.1016/j.mcat.2017.07.022

Cited by 30 publications

(22 citation statements)

References 69 publications

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“…Visible light is an attractive tool for such flux activation, because of its high resolution, temporal and spatial control, repeatability, and absence of contamination, since there is no need for physical contact between the stimulus source and the material. In the field of dynamic self‐assembly, light has been used to control both the formation and the disintegration of self‐assembled structures; for instance, the catalytic function of nanoparticles has been facilitated by such light‐powered self‐assembly …”

Section: Figurementioning

confidence: 99%

“…In the field of dynamic self-assembly, light has been used to control both the formation and the disintegration of self-assembled structures; [3,4] for instance, the catalytic function of nanoparticles has been facilitated by such light-powered self-assembly. [5,6] Controlling the encapsulation of various cargo in selfassembled micellar structures is crucial for such networked chemical systems, since the micelles can act as both nanoreactors for reactions with incompatible chemistries with the rest of the system, as well as transient carriers of molecular cargo between two distinct locations in the system. [3] Furthermore, micelles and vesicles for controlled encapsulation and delivery are already well-established in nanomedicine, water decontamination, fertilizers, insect repellents, and food packaging.…”

Section: Photobreathing Zwitterionic Micellesmentioning

confidence: 99%

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Photobreathing Zwitterionic Micelles

Niskanen

Vapaavuori

2019

ChemSystemsChem

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A significant and reversible size change (up to 80 nm, representing 100 % increase in diameter, i. e. “breathing”) of polymeric micelles of poly(styrene)‐block‐poly(3‐(4‐vinylpyridin‐1‐ium‐1‐yl)propane‐1‐sulfonate) (PS‐P4VP‐zwitter) was observed during phototriggered loading and release of spiropyran. The breathing (i. e. “inhaling/exhaling” of the small molecules by the micelles) could be controlled by switching the wavelength of the light used. Spiropyran, which was converted into the zwitterionic merocyanine by UV light, was readily diffused and incorporated into the zwitterionic micelle cores, thus causing the micelles to expand. At the same time, the merocyanine was stabilized by the polyzwitterionic core of the micelles. To the best of our knowledge, this is the first report of a supramolecular and reversibly photoloadable system that can be converted from a thermodynamically stable self‐assembled equilibrium system into a dynamic, self‐assembled system that is sustained by illumination.

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Section: Figurementioning

confidence: 99%

Section: Photobreathing Zwitterionic Micellesmentioning

confidence: 99%

Photobreathing Zwitterionic Micelles

Niskanen

Vapaavuori

2019

ChemSystemsChem

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“…[27,28] However,U V light switchable polymer-supported catalysts have been limited to regulating enzyme activity [13,29,30] and azobenzene containing molecularly imprinted polymers. [31,32] SP containing block co-polymers have been successfully synthesized through atom transfer radical polymerization (ATRP) or reversible addition-fragmentation chain transfer (RAFT) polymerization. [13] For instance, poly(ethylene oxide)-b-poly(styrene)-b-poly(SP methacrylate)w as obtained by ATRP and selfassembled into nanosized micelles in water.…”

Section: Introductionmentioning

confidence: 99%

Reversible Photoswitching in Poly(2‐oxazoline) Nanoreactors

Kuepfert

Cohen

et al. 2020

Chemistry A European J

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This contribution reports light responsive catalytic nanoreactors based on poly(2‐oxazoline) diblock copolymers. The hydrophobic block of the copolymer is a random copolymer consisting of a spiropyran functionalized 2‐oxazoline (SPOx) and 2‐(but‐3‐yn‐1‐yl)‐4,5‐dihydrooxazole (ButynOx), while the hydrophilic block is based on 2‐methyl‐2‐oxazoline (MeOx). The block copolymer is terminated with tris(2‐aminoethyl) amine (TREN) that serves as catalyst in a Knoevenagel condensation. Four block copolymers with different ButynOx/SPOx and hydrophilic/hydrophobic ratios are synthesized and self‐assembled through solvent exchange. Micelles and vesicles of various sizes are observed by TEM, which undergo morphological and size changes in response to irradiation with UV light. We hypothesize that these transformations in the nanostructures are caused by increases in the hydrophilicity of the hydrophobic block when spiropyran (SP) isomerizes to merocyanine (MC) in the presence of UV light. The reversible transition from micellar to vesicular nanoreactors resulted in increased reaction kinetics through improved substrate accessibility to the catalytic site, or termination of the catalytic reaction due to polymer precipitation. These nanoreactors present a promising platform towards photoregulating reaction outcomes based on changes in nanostructure morphology.

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“…Meanwhile, those imprinted cavities are endowed with the established ability to recognize the target analyte, i.e., template molecules (Xu et al, 2013). MIPs are widely applied in purification and separation (Li et al, 2015;Gong et al, 2017a;He et al, 2018;Zhang et al, 2018;Gomez-Arribas et al, 2019), chiral recognition (Rutkowska et al, 2018;Zhao et al, 2019;Li et al, 2020), chemo-and bio-sensing (Altintas et al, 2016;Gong et al, 2017b;Ding et al, 2020;Kalecki et al, 2020), and catalysis and degradation (Liu et al, 2015;Zheng et al, 2017;Boitard et al, 2019;Muratsugu et al, 2020) due to its physical stability, thermal stability, low cost, and ease of preparation.…”

Section: Introductionmentioning

confidence: 99%

Photoresponsive Surface Molecularly Imprinted Polymers for the Detection of Profenofos in Tomato and Mangosteen

Chen

Yang

et al. 2020

Front. Chem.

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As a moderately toxic organophosphorus pesticide, profenofos (PFF) is widely used in agricultural practice, resulting in the accumulation of a high amount of PFF in agricultural products and the environment. This will inevitably damage our health. Therefore, it is important to establish a convenient and sensitive method for the detection of PFF. This paper reports a photoresponsive surface-imprinted polymer based on poly(styrene-co-methyl acrylic acid) (PS-co-PMAA@PSMIPs) for the detection of PFF by using carboxyl-capped polystyrene microspheres (PS-co-PMAA), PFF, 4-((4-(methacryloyloxy)phenyl)diazenyl) benzoic acid, and triethanolamine trimethacrylate as the substrate, template, functional monomer, and cross-linker, respectively. PS-co-PMAA@PSMIP shows good photoresponsive properties in DMSO/H 2 O (3:1, v/v). Its photoisomerization rate constant exhibits a good linear relationship with PFF concentration in the range of 0∼15 µmol/L. PS-co-PMAA@PSMIP was applied for the determination of PFF in spiked tomato and mangosteen with good recoveries ranging in 94.4-102.4%.

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An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

Cited by 30 publications

References 69 publications

Photobreathing Zwitterionic Micelles

Photobreathing Zwitterionic Micelles

Reversible Photoswitching in Poly(2‐oxazoline) Nanoreactors

Photoresponsive Surface Molecularly Imprinted Polymers for the Detection of Profenofos in Tomato and Mangosteen

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