Synthesis of diblock copolymers bearing p-methoxyphenacyl side groups

Free-standing, stimuli-responsive polyelectrolyte multilayer films enabled by light-induced degradation of sacrificial compartments are introduced. Two examples are described: i) a triple responsive film that uses light, redox, and pH for different functions, and ii) different wavelengths of light for different functions. This approach to multiresponsive materials offers simple design and chemical synthesis while enabling different stimuli to perform separate functions in the same material.

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“…Materials : Rhodamine‐labeled PEI, MNBMA, CMA, 2‐[(2‐hydroxyethyl)disulfanyl]ethyl methacrylate, and MPMA were synthesized as reported elsewhere …”

Section: Methodsmentioning

confidence: 99%

Stimuli‐Responsive Free‐Standing Layer‐By‐Layer Films

McIntosh

Simon

et al. 2015

Advanced Materials

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“…Light‐responsiveness is usually imparted to block copolymers by the incorporation of photosensitive moieties into their structure, either at the junction between two blocks12–20 or as side‐groups located along one or more of the sequences 21–34. Besides the well‐known azobenzenes, derivatives of 2‐nitrobenzyl alcohols have become one of the most famous photosensitive moieties used in polymer science.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and self‐assembly of diblock copolymers bearing 2‐nitrobenzyl photocleavable side groups

Schumers

Bertrand

Fustin

et al. 2011

J. Polym. Sci. A Polym. Chem.

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The light-responsive behavior in solution and in thin films of block copolymers bearing 2-nitrobenzyl photocleavable esters as side groups is discussed in this article. The polymers were synthesized by grafting 2-nitrobenzyl moieties onto poly(acrylic acid)-block-polystyrene (PAA-b-PS) precursor polymers, leading to poly(2-nitrobenzyl acrylaterandom-acrylic acid)-block-polystyrene (P(NBA-r-AA)-b-PS) block copolymers. The UV irradiation of the block copolymers in a selective solvent for PS led to the formation of micelles that were used to trap hydrophilic molecules inside their core (light-induced encapsulation). In addition, thin films consisting of light-responsive P(NBA-r-AA) cylinders surrounded by a PS matrix were achieved by the self-assembly of P(NBA-r-AA)b-PS copolymers onto silicon substrates. Exposing these films to UV irradiation generates nanostructured materials containing carboxylic acids inside the cylindrical nanodomains. The availability of these chemical functions was demonstrated by reacting them with a functional fluorescent dye. V C 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: 599-608, 2012

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“…Especially o -nitrobenzyl chromophores are discussed as promising candidates for biological applications since even stimulation with NIR light is possible (see Section 3.3 ). Consequently, several block copolymers bearing o -nitrobenzyl ester groups in the side chain in combination with blocks of PEO/PEG or POEGMA [ 89 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 ], polystyrene [ 98 , 99 , 100 ], poly(methyl acrylate) [ 101 ], poly(2-ethyl-2-oxazoline) [ 102 ], or polydimethylacrylamide [ 103 ] have been synthesized and investigated towards their response upon irradiation with far UV light. Exemplarily, Liu and Dong showed the photo-controlled release of the anticancer drug doxorubicin from a biodegradable polypeptide-based poly( S -( o -nitrobenzyl)- l -cysteine)- block -poly(ethylene oxide) block copolymer.…”

Section: λ-Dependent Photo-response In Block Copolymer Nanostructumentioning

confidence: 99%

“…This approach enables the regulation of the amphiphilic imbalance and the crosslinking density of block polymer micelles simultaneously. The afore-mentioned p -methoxy-phenacyl esters are also the subject of more recent works by Bertrand et al [ 98 , 142 ]. Thereby, the absence of a nitro group facilitates controlled polymerization procedures of the respective monomers rendering these compounds favorable if compared to the previously discussed nitrobenzyl esters.…”

Section: λ-Dependent Photo-response In Block Copolymer Nanostructumentioning

confidence: 99%

Micellization of Photo-Responsive Block Copolymers

2017

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This review focuses on block copolymers featuring different photo-responsive building blocks and self-assembly of such materials in different selective solvents. We have subdivided the specific examples we selected: (1) according to the wavelength at which the irradiation has to be carried out to achieve photo-response; and (2) according to whether irradiation with light of a suitable wavelength leads to reversible or irreversible changes in material properties (e.g., solubility, charge, or polarity). Exemplarily, an irreversible change could be the photo-cleavage of a nitrobenzyl, pyrenyl or coumarinyl ester, whereas the photo-mediated transition between spiropyran and merocyanin form as well as the isomerization of azobenzenes would represent reversible response to light. The examples presented cover applications including drug delivery (controllable release rates), controlled aggregation/disaggregation, sensing, and the preparation of photochromic hybrid materials.

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Synthesis of diblock copolymers bearing p-methoxyphenacyl side groups

Cited by 18 publications

References 30 publications

Stimuli‐Responsive Free‐Standing Layer‐By‐Layer Films

Stimuli‐Responsive Free‐Standing Layer‐By‐Layer Films

Synthesis and self‐assembly of diblock copolymers bearing 2‐nitrobenzyl photocleavable side groups

Micellization of Photo-Responsive Block Copolymers

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