Rearrangement of azoxybenzocrowns into chromophoric hydroxyazobenzocrowns and the use of hydroxyazobenzocrowns for the synthesis of ionophoric biscrown compounds

Szarmach, Mirosław; Wagner‐Wysiecka, Ewa; Luboch, Elżbieta

doi:10.1016/j.tet.2013.10.074

Cited by 13 publications

(36 citation statements)

References 29 publications

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“…On the basis of our many years, extensive experience with this type of compounds e.g. [4] we may conclude that this may indicate distinctly different complexation properties of these isomers in favor of the trans – trans isomer. The trans – trans isomer should be capable of forming an intramolecular sandwich-type complex (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…azobenzocrown ethers. Numerous macrocyclic compounds with inherent 2,2′-azobenzene moieties were synthesized and studied exhaustively [1–4]. Broad possibilities for functionalization of azobenzocrowns result in their potential applications in a variety of fields, e.g.…”

Section: Introductionmentioning

confidence: 99%

“…Broad possibilities for functionalization of azobenzocrowns result in their potential applications in a variety of fields, e.g. lipophilic crowns may be successfully used as ionophores, both in classic and miniature solid contact ion-selective membrane electrodes (ISEs) [2–4]. …”

Section: Introductionmentioning

confidence: 99%

“…We obtained and used in the membrane ion-selective electrodes a number of 13-membered azobenzocrowns with modifications within the benzene rings, including crowns with: hydrocarbon moieties, hydrocarbon moieties linked by an ether group, compounds with ester or amide groups within the side chains or bis(azobenzocrown)s with two azobenzocrowns connected via an α,ω-dioxaalkane [2–4]. …”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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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“…4′-Hydroxyazobenzo-13-crown-4 ( 1 ) and 4′-hydroxyazobenzo-16-crown-5 ( 2 ) (Fig. 1 ) were prepared as previously described [ 56 ]. Compound 16 (Fig.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of thiol derivatives of azobenzocrown ethers. The preliminary studies on recognition of alkali metal ions by gold nanoparticles functionalized with azobenzocrown and lipoic acid

Luboch

Szarmach

Buczkowska

et al. 2015

J Incl Phenom Macrocycl Chem

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The article presents the synthesis of novel 13- and 16-membered azobenzocrown derivatives with peripheral thiol moieties and preliminary studies assessing their possible application in plasmonic sensors based on gold nanoparticles. The effect of the length of the chain connecting the macrocycle with the thiol group and the effect of the presence of the additional functional compound, i.e. lipoic acid, on the sensor response was analyzed. Colloidal gold nanoparticles modified with a 16-membered crown with a thiol group on oxyethylene (compound 12) or oxybutylene (compound 13) linker was found to have good properties, allowing for detection of potassium ions in aqueous solutions at concentrations 8-20 mM for bifunctionalized nanogold and 4-26 mM for less stable, colloidal gold modified only with thiol derivatives of azobenzocrowns. The response towards potassium cations of bifunctionalized nanogold modified with compound 13 was more stable in time than for the system incorporating compound 12. Compound 13, obtained with the highest yield among all presented thiol derivatives of azobenzocrowns, was selected for further, more detailed, studies.

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Photochemical Rearrangement of a 19‐Membered Azoxybenzocrown: Products and their Properties

et al. 2020

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The preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown are presented. In photochemical rearrangement, besides the expected product i. e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH) obtained under defined conditions with 75 % yield, also other macrocyclic products were isolated and identified, namely: 19-membered phydroxy-o,o'-azobenzocrown (19-p-OH), 21-membered o'hydroxy-o,p'-azobenzocrown (21-o'-OH) and 19-membered macrocycle containing a 5-membered ring bearing an aldehyde group (19-al). The structures of two atypical products of the photochemical rearrangement-21-o'-OH and 19-al-were determined in the solid state by X-ray analysis and in solution using NMR spectroscopy. Tautomeric equilibrium of the formed hydroxyazobenzocrowns and its change depending on acidity/ basicity of the environment and alkali and alkaline earth metal cations complexation were studied using UV-Vis spectrophotometry, spectrofluorimetry and 1 H NMR spectroscopy.

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Rearrangement of azoxybenzocrowns into chromophoric hydroxyazobenzocrowns and the use of hydroxyazobenzocrowns for the synthesis of ionophoric biscrown compounds

Cited by 13 publications

References 29 publications

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

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

Synthesis of thiol derivatives of azobenzocrown ethers. The preliminary studies on recognition of alkali metal ions by gold nanoparticles functionalized with azobenzocrown and lipoic acid

Photochemical Rearrangement of a 19‐Membered Azoxybenzocrown: Products and their Properties

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