Corrigendum to “Azobenzenes—synthesis and carbohydrate applications” [Tetrahedron 65 (49) (2008) 10105–10123]

Hamon, Florian; Djedaïni‐Pilard, Florence; Barbot, F.; Len, Christophe

doi:10.1016/j.tet.2010.01.057

Cited by 13 publications

(16 citation statements)

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“…Macrocycles containing one to several azobenzenes have been designed, synthesized, and investigated for light‐induced chirality transfers, ion complexation, multistate switches, optical storage devices, photoswitchable phase transition in liquid crystals and crystals, or as artificial molecular machines and molecular actuators. Photoresponsive glycosides have recently been developed for light‐controlled carbohydrate–protein interactions, cell adhesion, chiral discrimination, or as photosensitive protein cross‐linkers, surfactants, and gelators . Supramolecular gels represent remarkable functional soft nanomaterials with potential applications ranging from (bio)catalysis, chemosensors, drug delivery, cosmetics to optoelectronics, shape‐memory, and display devices .…”

Section: Methodsmentioning

confidence: 99%

“…Of particular interest for supramolecular constructs are “smart gels”, that is, gels whose properties can be controlled reversibly or irreversibly by external stimuli like chemical, photon, electron, temperature, or mechanical stress . Design and synthesis of photoswitchable carbohydrate‐based macrocycles should be very interesting for spatiotemporally controlling various chemical, structural, and biological properties of sugar‐based macrocyclic compounds by light . After preliminary design and molecular mechanics (MM2) calculations, we envisioned the synthesis of carbohydrate‐based macrocyclic azobenzene 1 bearing one 2,2′‐carboxymethoxyazobenzene moiety on the 4,6‐position of phenyl thio‐α‐ d ‐mannopyranoside (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

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Photoswitchable Carbohydrate‐Based Macrocyclic Azobenzene: Synthesis, Chiroptical Switching, and Multistimuli‐Responsive Self‐Assembly

Lin

Maisonneuve

Métivier

et al. 2017

Chemistry A European J

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A one-pot O-alkylation mediated macrocyclization approach has been used for the synthesis of carbohydrate-based macrocyclic azobenzene. The synthesized macrocycle can be reversibly isomerized between E and Z isomers upon UV or visible irradiation with excellent photostability and thermal stability (t =51 days at 20 °C for the Z isomer). A chirality transfer from the chiral sugar unit to azobenzene was observed by circular dichroism (CD). DFT and TD-DFT calculations were performed to calculate the optimal geometry and the theoretical absorption and CD spectra. Comparison of the experimental CD spectra with the theoretical ones suggests that both E- and Z-macrocycles adopt preferentially P-helicity for the azobenzene moiety. Furthermore, the macrocycle showed gelation ability in cyclohexane and ethanol with multistimuli-responsive behavior upon exposure to environmental stimuli including thermal-, photo-, and mechanical responses. Moreover, these organogels display temperature-dependent helical inversion, which can be tuned by a repeated heating-cooling procedure.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Photoswitchable Carbohydrate‐Based Macrocyclic Azobenzene: Synthesis, Chiroptical Switching, and Multistimuli‐Responsive Self‐Assembly

Lin

Maisonneuve

Métivier

et al. 2017

Chemistry A European J

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“…More specifically, we expected that the flat trans isomer of the compound should be able to fit in the tight gap in the active site. Upon photoisomerization to the cis form of the azobenzene, a large conformational change from a planar to a bent structure is observed 27–29. We envisioned that the large change in geometry and steric effects caused by the nonplanar cis conformation of the molecule would prevent its binding to the proteasome active sites.…”

Section: Methodsmentioning

confidence: 99%

The Effect of Water on the Heterogeneously Catalyzed Selective Oxidation of Acrolein: An Isotope Study

Petzold¹,

Blickhan²,

Drochner³

et al. 2014

ChemCatChem

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The effect of water on the selective gas phase oxidation of acrolein to acrylic acid on a Mo/V/W mixed oxide catalyst was studied by performing steady‐state isotopic transient kinetic analysis experiments with H218O. Experiments were performed in the temperature range of 90–345 °C at ambient pressure. It could be shown that acrolein exchanges its carbonylic oxygen with oxygen from water even at low temperatures (<200 °C), at which no acrolein oxidation occurs. At higher temperatures (>200 °C), the oxygen atoms of the water molecules incorporate into all oxidation products such as acrylic acid, carbon monoxide, and carbon dioxide.

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“…For example, they are used in solar cells and solar thermal fuels, sensors, photopharmacology, and biomedical applications . Furthermore, they have been incorporated as molecular switches into polymers and carbohydrates as well as into biological systems such as oligonucleotides, peptides, and proteins . And azo derivatives have also been used in the design of (photoswitchable) ligands for duplex and quadruplex DNA .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties

Pithan

Kuhlmann

Engelhard

et al. 2019

Chemistry A European J

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A series of new 5‐mono‐ and 5,5′‐bisamino‐substituted azothiazole derivatives was synthesized from the readily available diethyl azothiazole‐4,4′‐dicarboxylate. This reaction most likely comprises an initial Michael‐type addition by the respective primary alkyl and aromatic amines at the carbon atom C5 of the substrate. Subsequently, the resulting intermediates are readily oxidized by molecular oxygen to afford the amino‐substituted azothiazole derivatives. The latter exhibit remarkably red‐shifted absorption bands (λabs=507–661 nm) with high molar extinction coefficients and show a strong positive solvatochromism. As revealed by spectrometric titrations and circular and linear dichroism studies, the water‐soluble, bis‐(dimethylaminopropylamino)‐substituted azo dye associates with duplex DNA by formation of aggregates along the phosphate backbone at high ligand–DNA ratios (LDR) and by intercalation at low LDR, which also leads to a significant increase of the otherwise low emission intensity at 671 nm.

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Corrigendum to “Azobenzenes—synthesis and carbohydrate applications” [Tetrahedron 65 (49) (2008) 10105–10123]

Cited by 13 publications

References 0 publications

Photoswitchable Carbohydrate‐Based Macrocyclic Azobenzene: Synthesis, Chiroptical Switching, and Multistimuli‐Responsive Self‐Assembly

Photoswitchable Carbohydrate‐Based Macrocyclic Azobenzene: Synthesis, Chiroptical Switching, and Multistimuli‐Responsive Self‐Assembly

The Effect of Water on the Heterogeneously Catalyzed Selective Oxidation of Acrolein: An Isotope Study

Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties

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