Synthesis and properties of azobenzocrown ethers with π-electron donor, or π-electron donor and π-electron acceptor group(s) on benzene ring(s)

Luboch, Elżbieta; Wagner‐Wysiecka, Ewa; Poleska-Muchlado, Z.; Kravtsov, Victor Ch.

doi:10.1016/j.tet.2005.08.071

Cited by 33 publications

(33 citation statements)

References 21 publications

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“…Furthermore, Fig. 3 inferred an order of the adsorption capacity as 2,4-DCP > p-CP > o-CP > P. The adsorption of 2,4-DCP on carbons was controlled by the synergetic effects of -interaction and electrostatic attraction, and the former was dominant, especially when pH < pK a [23,24]. The -interaction derives from the interactions between the electrons in the aromatic rings of the 2,4-DCP and the graphene layers, which might comprise charge-transfer, dispersive force and polar electrostatic components [25].…”

Section: Competitive Adsorption Of Four Substances On Mwntsmentioning

confidence: 92%

Simultaneous adsorption and dechlorination of 2,4-dichlorophenol by Pd/Fe nanoparticles with multi-walled carbon nanotube support

Xu¹,

Lv²,

Li³

et al. 2012

Journal of Hazardous Materials

120

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Section: Competitive Adsorption Of Four Substances On Mwntsmentioning

confidence: 92%

Simultaneous adsorption and dechlorination of 2,4-dichlorophenol by Pd/Fe nanoparticles with multi-walled carbon nanotube support

Xu¹,

Lv²,

Li³

et al. 2012

Journal of Hazardous Materials

120

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“…Chromoionophoric properties are also observed e.g. for azobenzocrowns featuring amine substituents within the benzene ring and pull – push type azobenzocrowns featuring nitro and dimethylamine groups within the benzene rings [2, 9]. …”

Section: Introductionmentioning

confidence: 99%

New bis(azobenzocrown)s with dodecylmethylmalonyl linkers as ionophores for sodium selective potentiometric sensors

Luboch

Jeszke

Szarmach

et al. 2016

J Incl Phenom Macrocycl Chem

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Novel biscrowns 1 and 2 were synthesized from 13-membered azobenzocrown ethers containing bromoalkylenoxy chains in para position relative to the azo group. The synthesized diester molecules are dodecylmethylmalonic acid derivatives differing by the linker length. The synthesized compounds have the potential of being used as sodium ionophores in ion-selective electrodes. They were characterized and used as ionophores in classic and miniature, solid contact (screen-printed and glassy carbon) membrane ion-selective electrodes. Compound 3, a similar monoester derivative of 13-membered azobenzocrown, was synthesized and used in membrane electrodes for comparison. Lipophilicity of new ionophores was determined by TLC. Lipophilicity of bis(azobenzocrown)s was found to be within the range of logPTLC = 12–13. It was observed that the particularly important selectivity coefficients logK Na,K determined for new electrodes, being logK Na,K = −2.5 and −2.6 (SSM, 0.1 M), are better than those of the electrodes featuring seven out of the nine commercially available sodium ionophores. It was concluded that the ionophore 1 creates, in acetone, with sodium iodide, complex of 1:1 stoichiometry (sandwich complex) with stability constant (logK) ca. 3.0.

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“…[1][2][3][4] Changes in geometry and electronic structure upon isomerization enable AB to be used as a light-triggered switch. Azobenzene photoswitches have been used to tune the binding affinity of metal-chelators, [5,6] modulate the activity of biological probes, [7,8] influence catalysis, [9,10] design molecular machines, [11,12] cause structural changes in photoresponsive polymeric materials, [13,14] and alter the photochemical properties of liquid crystals, [15,16] holographic data storage devices, [17,18] and optical gratings. [19,20] Despite the prevalence of AB derivatives in a broad spectrum of chemical applications, light is the sole input for controlling isomerization.…”

Section: Introductionmentioning

confidence: 99%

Systematic Modulation of Hydrogen Bond Donors in Aminoazobenzene Derivatives Provides Further Evidence for the Concerted Inversion Photoisomerization Pathway

et al. 2013

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A series of aminoazobenzene derivatives structurally related to AzoAMP‐1 have been prepared and characterized by using a variety of analytical techniques. AzoAMP‐1 is based on 2,2′‐diaminoazobenzene with N‐methylpyridine groups. The new derivatives all contain a hydrogen bond between the aniline hydrogen atom and the azo group, as well as a separate pendant functional group that could contribute an additional hydrogen‐bond acceptor to an intramolecular network. A combination of photoisomerization studies and NMR spectroscopic and X‐ray crystallographic investigations suggest that AzoAMP‐1 possesses a unique structure that prevents isomerization through the concerted inversion pathway, which cannot be reproduced with other types or arrangements of substituents. Only AzoAMQ, which contains a similar quinolone heterocycle in place of the pyridine group of AzoAMP‐1, displayed somewhat similar photochemistry.

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Synthesis and properties of azobenzocrown ethers with π-electron donor, or π-electron donor and π-electron acceptor group(s) on benzene ring(s)

Cited by 33 publications

References 21 publications

Simultaneous adsorption and dechlorination of 2,4-dichlorophenol by Pd/Fe nanoparticles with multi-walled carbon nanotube support

Simultaneous adsorption and dechlorination of 2,4-dichlorophenol by Pd/Fe nanoparticles with multi-walled carbon nanotube support

New bis(azobenzocrown)s with dodecylmethylmalonyl linkers as ionophores for sodium selective potentiometric sensors

Systematic Modulation of Hydrogen Bond Donors in Aminoazobenzene Derivatives Provides Further Evidence for the Concerted Inversion Photoisomerization Pathway

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