Cation sensing by diphenyl-azobenzocrowns

Wagner‐Wysiecka, Ewa; Szarmach, Mirosław; Chojnacki, Jarosław; Łukasik, Natalia; Luboch, Elżbieta

doi:10.1016/j.jphotochem.2016.10.028

Cited by 14 publications

(24 citation statements)

References 44 publications

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“…The 1 H NMR studies of tautomeric equilibrium of hydroxyazobenzocrowns with phenyl substituents in benzene rings (Fig. 51 ) showed that 13-membered crown 109 in acetonitrile exists in quinone-hydrazone form [ 191 ]. 10% of azophenol form was detected in DMSO.…”

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

“…10% of azophenol form was detected in DMSO. For 16-membered crown 110 the presence of quinone-hydrazone form was stated in acetone and chloroform [ 191 ] and also in DMSO (50%).…”

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

“…

Fig. 53 Comparison of stability constant values of complexes of 23, 75 and 110 in neutral and basic acetonitrile calculated from UV–Vis titrations [ 133 , 166 , 191 ] …”

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

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Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.

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Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

“…10% of azophenol form was detected in DMSO. For 16-membered crown 110 the presence of quinone-hydrazone form was stated in acetone and chloroform [ 191 ] and also in DMSO (50%).…”

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

“…

Fig. 53 Comparison of stability constant values of complexes of 23, 75 and 110 in neutral and basic acetonitrile calculated from UV–Vis titrations [ 133 , 166 , 191 ] …”

Section: Functionalized Azobenzocrowns (Azo Moiety As a Part Of The Mmentioning

confidence: 99%

See 2 more Smart Citations

Azo group(s) in selected macrocyclic compounds

Wagner‐Wysiecka

Łukasik

Biernat

et al. 2018

J Incl Phenom Macrocycl Chem

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“…Azo phenol quinone hydrazone tautomerism is the well-known phenomenon in the case of azo-substituted azobenzenes in ortho or para in an azo moiety [54]. Figure 34 illustrates an example of hydroxyazobenzene tautomerism of hydroxy azobenzene rings [55].…”

Section: Isomerism Z/ementioning

confidence: 99%

Classifications, properties, recent synthesis and applications of azo dyes

Benkhaya

M’rabet

Harfi

2020

Heliyon

591

187

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In this work, we have presented a very detailed review of the different classification of azo dyes as a function of the number of azo groups and the appropriate functional groups. Then we pointed out some chemical properties of these dyes such as reactivity, isomerization and tautomerism and listed. In the following, we have summarized some recent syntheses of azo dyes and the mechanism of azo dye/polymer conjugation. Finally, we indicate the principle of Gewald's reaction and its application to the synthesis of new azo dyes.

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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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Cation sensing by diphenyl-azobenzocrowns

Cited by 14 publications

References 44 publications

Azo group(s) in selected macrocyclic compounds

Azo group(s) in selected macrocyclic compounds

Classifications, properties, recent synthesis and applications of azo dyes

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

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