A ferrocene–azobenzene derivative showing unprecedented phase transition and better solubility upon UV irradiation

Zhang, Rui; Ji, Ya-Jian; Yang, Lan; Zhang, Yi; Kuang, Gui‐Chao

doi:10.1039/c6cp00507a

Cited by 15 publications

(9 citation statements)

References 25 publications

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“…The onset of fluidization is consistent with previous reports on UV-induced amorphization of azobenzene-based polymer films17, and softening in pure crystals of azobenzene molecules1041424344 and azobenzene-doped elastomers283145, which has been attributed to the higher free volume requirements of the cis bent conformation compared with the trans isomer2746. We therefore postulate that blue light-induced fluidization facilitates the co-alignment of kinetically-trapped, randomly arranged mesostructured domains in the trans -azoTAB:PAA particles such that the irregular particles of trans -azoTAB:PAA are reconfigured into hexagonal platelets with well-defined low energy faces.…”

Section: Discussionsupporting

confidence: 91%

Light-induced dynamic shaping and self-division of multipodal polyelectrolyte-surfactant microarchitectures via azobenzene photomechanics

Martin

Sharma

Harniman

et al. 2017

Sci Rep

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Light-induced shape transformations represent a fundamental step towards the emergence of adaptive materials exhibiting photomechanical behaviours. Although a range of covalent azobenzene-based photoactive materials has been demonstrated, the use of dynamic photoisomerization in mesostructured soft solids involving non-covalent co-assembly has received little attention. Here we prepare discrete micrometre-sized hydrated particles of a hexagonally ordered polyelectrolyte-surfactant mesophase based on the electrostatically induced co-assembly of poly(sodium acrylate) (PAA) and trans-azobenzene trimethylammonium bromide (trans-azoTAB), and demonstrate unusual non-equilibrium substrate-mediated shape transformations to complex multipodal microarchitectures under continuous blue light. The microparticles spontaneously sequester molecular dyes, functional enzymes and oligonucleotides, and undergo self-division when transformed to the cis state under UV irradiation. Our results illustrate that weak bonding interactions in polyelectrolyte-azobenzene surfactant mesophases can be exploited for photo-induced long-range molecular motion, and highlight how dynamic shape transformations and autonomous division can be activated by spatially confining azobenzene photomechanics in condensed microparticulate materials.

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Section: Discussionsupporting

confidence: 91%

Light-induced dynamic shaping and self-division of multipodal polyelectrolyte-surfactant microarchitectures via azobenzene photomechanics

Martin

Sharma

Harniman

et al. 2017

Sci Rep

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“…Some evidence of photo-induced solubilization change has already been reported for azobenzenes 11 , 25 , 26 or azo-poly(glutamic acid), azo-poly(ornithine) and azo-poly(diaminopropanoic acid) 27 – 30 . However, because of the essentially hydrophobic character of azobenzene, those studies were limited to turbidity measurements in organic solvents 11 , 25 , 26 or organic solvent/water mixtures 27 – 30 . On the other hand, water has many advantages as a solvent, such as environmentally friendly and non-inflammable character, and is irreplaceable in medical and biological applications.…”

Section: Introductionmentioning

confidence: 83%

Photo-enhanced Aqueous Solubilization of an Azo-compound

Ishikawa

Ohzono

Yamaguchi

et al. 2017

Sci Rep

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We previously showed that disruption of intermolecular interactions, e.g., by lowering the molecular planarity and/or introducing bent structures, improves the aqueous solubility of compounds, and based upon that work, we hypothesized that azobenzene trans-to-cis photoswitching could also be utilized to enhance the aqueous solubility of compounds. Here, we demonstrate that UV/visible light irradiation can reversibly switch the aqueous solubilization of an anti-cancer candidate drug, a low-molecular-weight kinase inhibitor bearing an azobenzene moiety. The increase of solubilization associated with UV-induced trans-to-cis conversion may have clinical relevance, because the time-scale of thermal cis-to-trans reversion at 37 °C is longer than that of oral absorption.

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“…Section 3 for a more detailed overview). In this context, classical azobenzene photoswitches were studied regarding the difference in solubility between the planar E and the helical Z isomer, [630][631][632][633] in which the phenyl rings are twisted out of plane. 634 For instance, the solubility difference of the E and Z isomers was tested for azobenzenes 4.31 and 4.32, 635 where the Z isomer was 20-times (4.31) or 1.4-times (4.32), respectively, more soluble in phosphate buffer then the E form (Fig.…”

Section: Dae and Fulgimidesmentioning

confidence: 99%

Molecular photoswitches in aqueous environments

et al. 2021

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A ferrocene–azobenzene derivative showing unprecedented phase transition and better solubility upon UV irradiation

Abstract: The ferrocene-aspartic acid-azobenzene derivative 1 showing an unprecedented photoinduced crystal-liquid phase transition at an elevated temperature and better solubility in organic solvents has been successfully reported.

Cited by 15 publications

References 25 publications

Light-induced dynamic shaping and self-division of multipodal polyelectrolyte-surfactant microarchitectures via azobenzene photomechanics

Light-induced dynamic shaping and self-division of multipodal polyelectrolyte-surfactant microarchitectures via azobenzene photomechanics

Photo-enhanced Aqueous Solubilization of an Azo-compound

Molecular photoswitches in aqueous environments

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