Titelbild: Orthogonal Light‐Induced Self‐Assembly of Nanoparticles using Differently Substituted Azobenzenes (Angew. Chem. 42/2015)

Manna, Debasish; Udayabhaskararao, Thumu; Zhao, Hui; Klajn, Rafał

doi:10.1002/ange.201507476

Cited by 2 publications

(1 citation statement)

References 27 publications

(40 reference statements)

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“…While the linear trans isomer is non-polar, the bent cis isomer becomes highly polar (∼3-6 D) 3 due to the change in its symmetry. These features, together with their relative simple preparation, made azobenzene based materials widely explored as molecular platforms for application such as photo-activated drugs, 4,5 drug delivery systems, [6][7][8] protein channels, [9][10][11] nano-particles, 12 photoresponsive surfaces, 13 catalysis, 14 etc. In the emerging field of smart polymers, azobenzene derivatives were incorporated into the backbone of block copolymers or as grafted sidegroups.…”

Section: Introductionmentioning

confidence: 99%

The effect of photoisomerization on the enzymatic hydrolysis of polymeric micelles bearing photo-responsive azobenzene groups at their cores

et al. 2016

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The design of stable polymeric micelles that can respond to specific stimuli is crucial for the development of smart micellar nanocarriers that can release their active cargo selectively at the target site, thus diminishing the therapeutic limitations due to non-selective damage to healthy tissues. Here we report the design and synthesis of photo- and enzyme-responsive amphiphilic PEG-dendron hybrids bearing one, two or four enzymatically cleavable azobenzene end-groups. These dual-responsive hybrids can respond to light through the reversible isomerization of the azobenzene end-groups from the non-polar trans isomer to the highly polar cis isomer and vice versa, upon UV and visible irradiation, respectively. The high structural precision of these hybrids, which emerges from the dendritic architecture, enabled a detailed study of the photoisomerization of the azobenzene end-groups with high molecular resolution. Remarkably, although the transition from trans-to-cis led to a significant increase in the polarity of the micellar cores, the micelles remained stable. Our kinetic studies show that although the trans isomer is a better substrate for the activating enzyme, the UV induced formation of the cis azobenzene end-groups led to significant acceleration of the enzymatic hydrolysis of the end-groups. These results provide strong indication that the enzyme cannot reach the core of the micelles and instead the end-groups have to leave the hydrophobic core in order to be exposed on the micelle's surface or even leave the micelle in order to allow their cleavage by the activating enzymes.

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Section: Introductionmentioning

confidence: 99%

The effect of photoisomerization on the enzymatic hydrolysis of polymeric micelles bearing photo-responsive azobenzene groups at their cores

et al. 2016

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Photoswitching of azobenzene-containing self-assembled monolayers as a tool for control over silicon surface electronic properties

Malyar

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Lomadze

et al. 2017

The Journal of Chemical Physics

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We report on photoinduced remote control of work function and surface potential of a silicon surface modified with a photosensitive self-assembled monolayer consisting of chemisorbed azobenzene molecules (4-nitroazobenzene). It was found that the attachment of the organic monolayer increases the work function by hundreds of meV due to the increase in the electron affinity of silicon substrates. The change in the work function on UV light illumination is more pronounced for the azobenzene jacketed silicon substrate (ca. 250 meV) in comparison to 50 meV for the unmodified surface. Moreover, the photoisomerization of azobenzene results in complex kinetics of the work function change: immediate decrease due to light-driven processes in the silicon surface followed by slower recovery to the initial state due to azobenzene isomerization. This behavior could be of interest for electronic devices where the reaction on irradiation should be more pronounced at small time scales but the overall surface potential should stay constant over time independent of the irradiation conditions.

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Titelbild: Orthogonal Light‐Induced Self‐Assembly of Nanoparticles using Differently Substituted Azobenzenes (Angew. Chem. 42/2015)

Cited by 2 publications

References 27 publications

The effect of photoisomerization on the enzymatic hydrolysis of polymeric micelles bearing photo-responsive azobenzene groups at their cores

The effect of photoisomerization on the enzymatic hydrolysis of polymeric micelles bearing photo-responsive azobenzene groups at their cores

Photoswitching of azobenzene-containing self-assembled monolayers as a tool for control over silicon surface electronic properties

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