Mesomorphic and<i>trans–cis–trans</i>photoisomerization studies of 4-[2-(4-hexyloxyphenyl)diazenyl]phenyl alkanoates

Niezgoda, Izabela; Jaworska, Joanna; Kownacka, Małgorzata; Pociecha, Damian; Galewski, Zbigniew

doi:10.1080/01411594.2014.953507

Cited by 9 publications

(2 citation statements)

References 18 publications

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“…When photons of a suitable wavelength are utilized the azo‐compound transition from its more thermodynamically stable E configuration to its labile Z form occurs. This phenomenon is called light‐induced reversible isomerization, and its detailed mechanism, kinetics, and thermodynamics are still under investigation . The mentioned isomerization capability of these LCMs is useful and applicable in modern display technology as well as other fields such as separation and biomaterial sciences .…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

et al. 2017

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Chiral high-performance liquid chromatography separation of two recently synthesized liquid crystalline materials C1 and C2 was studied in the reversed-phase mode. Both materials have an azo-moiety and one chiral center in their molecular structures. They were available in racemic and pure S forms. For the enantiomeric separations, a Chiralpak AY-RH stationary phase based on amylose tris(5-chloro-2-methylphenylcarbamate) coated on 5 μm silica was used. The compounds were analyzed in both of their possible forms, the more thermodynamically stable E form and the labile Z form. The conditions and time scale of the UV-induced E to Z transition were briefly evaluated. Under the optimized conditions, we were able to baseline separate S and R enantiomers of both of the studied materials not only in their E forms, but also in their Z forms. In comparison to the separation in the normal-phase mode, which we have reported recently, the resolution in the reversed-phase mode is significantly better. Interestingly, peak reversal was noticed for the S and R enantiomers when the separation was carried out with E versus Z forms of both compounds.

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Section: Introductionmentioning

confidence: 99%

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

et al. 2017

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“…When photons of a suitable wavelength are applied to the azo compound, a transition from its more thermodynamically stable E configuration to its labile Z isomeric form occurs. This effect is called light‐induced reversible isomerization, and its detailed mechanism, kinetics, and thermodynamics are still under investigation . The thermally directed reverse transition of Z isomer to E isomer takes a relatively long time in many cases.…”

Section: Introductionmentioning

confidence: 99%

Influence of photoinduced isomerization on the chiral separation of novel liquid crystalline materials with a diazene moiety

Vojtylová

Cigl

Tomášková

et al. 2018

J of Separation Science

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The influence of photoinduced isomerization on the enantiomeric separation of two newly synthesized liquid crystalline materials, liquid crystals 1 and 2, was studied by high-performance liquid chromatography on a chiral stationary phase Chiralpack AD-3. Both materials have one chiral center and one diazene moiety. The compounds were separated into their E and Z isomeric forms. The conditions and time scale of the ultraviolet-induced E to Z transition were briefly evaluated. Under the optimized conditions, we were able to baseline separate the S and R enantiomers of both the studied materials in their E isomeric form. The chiral separation of liquid crystal 2 after ultraviolet irradiation was unsuccessful. In contrast, the chiral separation of liquid crystal 1 possessing a similar structure to liquid crystal 2 provided baseline separation in its Z isomeric form as well. Previously, we have shown the influence of photoinduced isomerization and its utilization in the enantioseparation on relatively simple molecules. Here, we demonstrate that (1) much more complex compounds can also be successfully separated despite the bulkiness of the achiral part of the structure and (2) photoinduced isomerization even for such complex molecules still strongly influences their chromatographic properties.

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Mesogenic properties and studies of the photoisomerization process in solutions of branched azobenzene derivatives with ester group

Niezgoda

Jaworska

Galewski

2016

Journal of Molecular Liquids

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Mesomorphic andtrans–cis–transphotoisomerization studies of 4-[2-(4-hexyloxyphenyl)diazenyl]phenyl alkanoates

Cited by 9 publications

References 18 publications

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

Chiral separation of novel diazenes on a polysaccharide-based stationary phase in the reversed-phase mode

Influence of photoinduced isomerization on the chiral separation of novel liquid crystalline materials with a diazene moiety

Mesogenic properties and studies of the photoisomerization process in solutions of branched azobenzene derivatives with ester group

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