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Skwierawska, Anna; Luboch, Elżbieta; Biernat, Jan F.; Kravtsov, Victor Ch.; Simonov, Yu. A.; Dvorkin, A. A.; Bel'skii, V. K.

doi:10.1023/a:1007945901754

Cited by 22 publications

(18 citation statements)

References 3 publications

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“…The previously developed synthetic procedure [8,10] leads to isomers of 13-and 16-membered azobenzocrown ethers. The * Torsion angles are taken from Ref.…”

Section: Discussionmentioning

confidence: 99%

“…Compounds 1 and 2 were obtained by the reduction of the respective bis(2-nitrophenoxy)-oxaalkanes with stannites, as described previously [8,10]. The resulting azobenzocrown (as a mixture of isomers) was extracted with boiling hexane and the solution was evaporated.…”

Section: Synthesismentioning

confidence: 99%

“…Compound 1 potassium complexes of this macrocycle (designated as L16) having the compositions [NaL16ÁI] [9] and [(KL16) 2 ÁIÁ(CH 3 ) 2 CHOH] [10], respectively. Using the aforementioned approach we compared the conformation of the free and coordinated macrocycle.…”

Section: Molecular Structure Of Compoundmentioning

confidence: 99%

“…In the sandwich-type complex [(KL16) 2 ÁIÁ(CH 3 ) 2 CHOH] [10] the coordination polyhedron of the K + ion is formulated by the NO 4 donor set of two unique crown molecules. Comparison of the set of torsion angles alongside the macrocyclic framework in the two complexes with those in the free ligand shows that it is close to that for the uncomplexed 2A molecule (Table 2, Fig.…”

Section: Molecular Structure Of Compoundmentioning

confidence: 99%

“…For the analogous 13-membered crown ether the structure of the free Z-isomer was also determined [6], but high-quality crystals of the E-isomer were available only in the form of Li + [7] or Na + [8] complexes. The E-isomer of azobenzo-16-crown-5 forms a 1:1 complex with Na + [9] and a sandwich-type complex with K + [10].…”

Section: Introductionmentioning

confidence: 99%

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Molecular structures of two E-azobenzocrown ethers

Fonarı¹,

Luboch²,

Collas³

et al. 2008

Journal of Molecular Structure

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“…The previously developed synthetic procedure [8,10] leads to isomers of 13-and 16-membered azobenzocrown ethers. The * Torsion angles are taken from Ref.…”

Section: Discussionmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Molecular Structure Of Compoundmentioning

confidence: 99%

Section: Molecular Structure Of Compoundmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Molecular structures of two E-azobenzocrown ethers

Fonarı¹,

Luboch²,

Collas³

et al. 2008

Journal of Molecular Structure

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Kinetics of photoinduced birefringence in the guest–host system of poly(methyl methacrylate) doped with azobenzene‐containing crown ethers

Shimizu

Volpati

Giacometti

et al. 2007

J of Applied Polymer Sci

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The kinetics of the buildup and decay of photoinduced birefringence was examined in a series of host-guest systems: azobenzene-containing crown ethers, differing in the size of the crowns, dissolved in a poly (methyl methacrylate) matrix. In all samples, the kinetics of the buildup of the birefringence was reasonably described by a sum of two exponential functions, the time constants being inversely proportional to the intensity of the pumping light and the magnitudes of the signals at the saturation level depending on the pumping light intensity and sample thickness. The dark decays were best described by the stretched exponential function, with the characteristic parameters (time constant and stretch coefficient) being practically independent of the type of crown ether. The time constants of the signal decay were orders of magnitude shorter than the respective constants of the dark isomerization of the azo crown ethers, thus indicating that the process controlling the decay was a relaxation of the polymer matrix and/or a rearrangement of the flexible parts of the crowns.

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Do Phenyl Substituents Affect the Properties of Azobenzocrown Derivatives?

Wagner‐Wysiecka,

Szulc,

Luboch

et al. 2023

ChemPlusChem

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New products of photo‐ and thermal rearrangements of 19‐membered azoxybenzocrown with phenyl substituents in benzene rings in the para positions to oligooxyethylene fragments are characterized in this work. The yields of photochemical transformations depend on the solvent. Para‐hydroxyazocrown is formed with yields over 50 % in propan‐2‐ol. Ortho‐hydroxyazobenzocrown is obtained with yields up to 70 % in toluene/acetic acid mixture. Macrocyclic Ph‐20‐ester is obtained in yield 90 % under thermochemical rearrangement conditions. Structure of new hydroxyazobenzocrowns and also atypical product of rearrangements, 20‐membered ester, was confirmed by X‐ray diffraction analysis. Azophenol ←0false→ ${ \mathbin{{\stackrel{\textstyle\rightarrow} { {\smash{\leftarrow}\vphantom{_{\vbox to.5ex{\vss}}}} } }} }$ quinone‐hydrazone tautomeric equilibrium of new hydroxyazobenzocrowns and the influence of metal cations on tautomeric equilibrium was investigated using 1H NMR and UV‐Vis spectroscopy in acetonitrile. The highest value of stability constant (logK 7.25) was obtained for strontium complex of p‐hydroxyazobenzocrown. For the first time p‐hydroxyazobenzocrown was used as a chromoionophore in the receptor layer of an optical sensor. Comparative analysis with data obtained previously for series 19‐membered analogs have shown the influence of the presence of substituents in benzene rings for the course and products distribution of photo and thermal rearrangement. The effect of substituents was also discussed against the tautomeric equilibrium and metal cation complexation properties.

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Cited by 22 publications

References 3 publications

Molecular structures of two E-azobenzocrown ethers

Molecular structures of two E-azobenzocrown ethers

Kinetics of photoinduced birefringence in the guest–host system of poly(methyl methacrylate) doped with azobenzene‐containing crown ethers

Do Phenyl Substituents Affect the Properties of Azobenzocrown Derivatives?

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