Photo-enhanced Aqueous Solubilization of an Azo-compound

Ishikawa, Minoru; Ohzono, Takuya; Yamaguchi, Takao; Norikane, Yasuo

doi:10.1038/s41598-017-06947-w

Cited by 22 publications

(13 citation statements)

References 34 publications

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“…55A). 636 A similar phenomenon regarding the solubility was also observed for some azopyridines discussed in Section 4.1.3 (vide supra). 625 The planarity in photoswitches can also be affected by attaching suitable substituents to the photoswitchable core.…”

Section: Dae and Fulgimidessupporting

confidence: 68%

Molecular photoswitches in aqueous environments

et al. 2021

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Section: Dae and Fulgimidessupporting

confidence: 68%

Molecular photoswitches in aqueous environments

et al. 2021

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“…36,37 We hypothesized that the E form favors assembly due to its planar hydrophobic nature, while the nonplanar and more polar Z form will destabilize monomer stacking and increase monomer solubility. 38 The second module of the wedge is an octa(ethylene glycol) amino acid (Figure 1 b, highlighted in blue), which grants flexibility and solubility in water, while it confers thermal responsivity due to its temperature-dependent hydrophilicity. 39−42 Finally, a Cterminal lysine (Figure 1b, highlighted in green) was added to enhance water solubility owing to the charged groups and induce the ampholytic character of this particular amino acid, which can result in dual pH and ionic strength response.…”

Section: Resultsmentioning

confidence: 99%

An Azobenzene-Based Single-Component Supramolecular Polymer Responsive to Multiple Stimuli in Water

et al. 2020

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One of the most appealing features of supramolecular assemblies is their ability to respond to external stimuli due to their noncovalent nature. This provides the opportunity to gain control over their size, morphology, and chemical properties and is key toward some of their applications. However, the design of supramolecular systems able to respond to multiple stimuli in a controlled fashion is still challenging. Here we report the synthesis and characterization of a novel discotic molecule, which self-assembles in water into a single-component supramolecular polymer that responds to multiple independent stimuli. The building block of such an assembly is a C 3 -symmetric monomer, consisting of a benzene-1,3,5-tricarboxamide core conjugated to a series of natural and non-natural functional amino acids. This design allows the use of rapid and efficient solid-phase synthesis methods and the modular implementation of different functionalities. The discotic monomer incorporates a hydrophobic azobenzene moiety, an octaethylene glycol chain, and a C-terminal lysine. Each of these blocks was chosen for two reasons: to drive the self-assembly in water by a combination of H-bonding and hydrophobicity and to impart specific responsiveness. With a combination of microscopy and spectroscopy techniques, we demonstrate self-assembly in water and responsiveness to temperature, light, pH, and ionic strength. This work shows the potential to integrate independent mechanisms for controlling self-assembly in a single-component supramolecular polymer by the rational monomer design and paves the way toward the use of multiresponsive systems in water.

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“…Azobenzene derivatives are photo-responsive compounds that exist as the trans and the cis isomer. The trans isomer exists under ambient light conditions, whereas the cis isomer is generated through irradiation with ultraviolet light [19]. The thermal cis to trans isomerisation, after irradiation, is proposed to proceed via in-plane inversion [20], out of plane rotation around the N=N double bond [21], or a combination of both [22], depending on the solvent polarity and the position and type of substituents.…”

Section: Photo-isomerisation Kinetics Of Azb(cooh) 2 Ligandmentioning

confidence: 99%

Trans–Cis Kinetic Study of Azobenzene-4,4′-dicarboxylic Acid and Aluminium and Zirconium Based Azobenzene-4,4′-dicarboxylate MOFs

2022

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Metal organic frameworks (MOFs) are porous hybrid crystalline materials that consist of organic linkers coordinated to metal centres. The trans–cis isomerisation kinetics of the azobenzene-4,4′-dicarboxylic acid (AZB(COOH)2) precursor, as well as the Al3+ (Al-AZB)- and Zr4+ (Zr-AZB)-based MOFs with azobenzene-4,4′-dicarboxylate linkers, are presented. The photo-isomerization in the MOFs originates from singly bound azobenzene moieties on the surface of the MOF. The type of solvent used had a slight effect on the rate of isomerization and half-life, while the band gap energies were not significantly affected by the solvents. Photo-responsive MOFs can be classified as smart materials with possible applications in sensing, drug delivery, magnetism, and molecular recognition. In this study, the MOFs were applied in the dye adsorption of congo red (CR) in contaminated water. For both MOFs, the UV-irradiated cis isomer exhibited a slightly higher CR uptake than the ambient-light exposed trans isomer. Al-AZB displayed a dye adsorption capacity of over 95% for both the UV-irradiated and ambient light samples. The ambient light exposed Zr-AZB, and the UV irradiated Zr-AZB had 39.1% and 44.6% dye removal, respectively.

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Photo-enhanced Aqueous Solubilization of an Azo-compound

Cited by 22 publications

References 34 publications

Molecular photoswitches in aqueous environments

Molecular photoswitches in aqueous environments

An Azobenzene-Based Single-Component Supramolecular Polymer Responsive to Multiple Stimuli in Water

Trans–Cis Kinetic Study of Azobenzene-4,4′-dicarboxylic Acid and Aluminium and Zirconium Based Azobenzene-4,4′-dicarboxylate MOFs

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