Favourable combination of axial coordination and inclusion for effective chiral transfer from metal porphyrin to nematic liquid crystals

Burmistrov, V. A.; Новиков, И. В.; Aleksandriiskii, V. V.; Семейкин, А. С.; Койфман, О. И.

doi:10.1080/02678292.2020.1817583

Cited by 9 publications

(19 citation statements)

References 55 publications

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“…The subjects of study included nematic LCs and chiral MHCs of various structures: nickel complex of octa-substituted tetraphenylporphine (Ni-(+)TPP), [23] symmetric camphor-substituted hemiporphyrazine ((+)HPA), [24] nickel complex of tetracamphoropyrazinoporphyrazine (Ni(À )TPPA), chlorin e6 13(N)-methylamide-15,17-dimethyl ether (MADMECl) and its metal complexes (M-MADMECl), [25,26] the structure of which is presented in Scheme 1.…”

Section: Discussionmentioning

confidence: 99%

“…Conclusions regarding the mechanism of chiral transport of NiÀ R(+)TPP -CB-2 are based on the description of the results given in. [23] Analysis of the data Table 3 indicates the general trends in the influence of the dopant structure on the intensity of interactions with both highly polar (cyanobiphenyls) and lowpolar (Schiff bases) LCs. Therefore, the introduction of a nickel ion leads to a significant increase in the solvation energy (ΔE) of the dopant by molecules of an anisotropic solvent.…”

Section: Discussionmentioning

confidence: 99%

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Chiral Macroheterocycles as Inducers of Helical Liquid Crystals: Molecular Design, Specialty of Functioning

Burmistrov,

Aleksandriiskii,

Novikov

et al. 2024

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The mini‐review is devoted to the influence of the structure and properties of chiral macroheterocyclic dopants on the induction of helical liquid‐crystalline phases. Using the example of solutions of synthetic porphyrins, camphor substituted hemiporphyrazines and tetrapyrazinoporphyrazines, as well as chemically modified natural macrocycles based on chlorin e6 derivatives and their metal complexes in nematic liquid crystals, the features of the mesomorphic, dielectric and rheological properties of induced spiral mesophases are discussed.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Chiral Macroheterocycles as Inducers of Helical Liquid Crystals: Molecular Design, Specialty of Functioning

Burmistrov,

Aleksandriiskii,

Novikov

et al. 2024

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“…A chiral nickel complex of 5,10,15,20-tetrakis[3,5-bis(2-methylbutoxy)phenyl]porphyrin was synthesized [ 119 – 121 ] (Scheme 2 ) and studied as a dopant in nematic mixtures based on strongly polar alkoxy cyano biphenyls and an eutectic mixture of weakly polar Schiff bases [ 119 ]. Anomalous temperature dependences of the components of the dielectric permittivity of liquid crystal solutions were found due to competition between the dopant which twists the mesophase and the magnetic field which tends to unwind the helix.…”

Section: Principal Methodologies Of the Synthesis Of Tetrapyrrole Mac...mentioning

confidence: 99%

Main Strategies for the Synthesis of meso-Arylporphyrins

Койфман

Агеева

2022

Russ J Org Chem

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meso -Arylporphyrins as most accessible tetrapyrrole macroheterocycles have always been the focus of attention from researchers concerned with practically useful properties of these compounds. The first syntheses of meso -arylporphyrins date back to about 90 years ago. Up to now, the yields of these compounds have been improved from 5 to 80%. The present review analyzes different ways and strategies for the synthesis of meso -aryl-substituted porphyrins. The most efficient methods that can be scaled up to an industrial level have been identified.

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“…В любом случае высокие значения НТР демонстрируют комплексы с объемными плоским ароматическими лигандами, обеспечивающими жесткий контакт с мезогенными молекулами и, следовательно, высокую эффективность хирального переноса. В работе [82] синтезирован хиральный октазамещенный тетрапорфиринат никеля (Ni-R(+) TPP), который был исследован в качестве допанта нематических смесей на основе сильнополярных алкоксицианобифенилов (СВ6) и эвтектической смеси слабополярных оснований Шиффа -МББА и ЭББА (SB-2) [82]. Анализ текстур жидкокристаллических растворов допанта позволил установить образование хиральных нематических фаз, измерить их температуры просветления, степень воздействия допанта на ЖК и значения шага спирали.…”

Section: хиральные металлокомплексные допантыunclassified

Mechanisms of Chiral Transfer in Optically Active Dopant – Nematic Liquid Crystal Systems

Burmistrov¹,

Aleksandriiskii²,

Новиков³

et al. 2020

Liq. Cryst. and their Appl.

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Induction of helical mesophases by incorporating chiral dopants into the nematics matrix is the promising modern trends in the chemistry of liquid crystals. This process is associated with a unique phenomenon - an amplification of chirality in liquid-crystalline phases, which ensures the detection of enantiomers by their chiral induction, much more sensitive than other methods. The relevance of this approach is due to the need to create perspective electro-optical devices operating with ultra-low control voltages based on twist effects, chromatographic stationary phases with high chiral selectivity, flexible magnets, photo-sensitive nanostructures, and other smart LC materials. The successful solution of these problems is impossible without experimental research and theoretical comprehension of the mechanisms of third level chiral transfer optically active dopant – nematic liquid crystal. In the last decade, a large number of works have appeared on the solution of these problems. This review is devoted to a generalization of the experimental results and a theoretical description of the transfer of molecular chirality to orientationally ordered systems with the participation of both chiral molecular substituents with an asymmetric carbon atom and planar or quasi-planar fragments chirally distorted relative to each other. The stereochemical aspects of induction associated with the structural correspondences of the dopant and nematic liquid crystal, as well as the main classes of optically active additives, are discussed. Application of metal complexes, both Werner and macroheterocyclic, are presented. Special attention is paid to the results of the mechanisms study of chiral transfer due to various intermolecular interactions: hydrogen bonding, axial coordination, and the formation of inclusion compounds. The high efficiency of induction of spiral mesophases has been demonstrated with a combination of different self-assembly mechanisms in liquid crystal - chiral additive systems.

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Favourable combination of axial coordination and inclusion for effective chiral transfer from metal porphyrin to nematic liquid crystals

Cited by 9 publications

References 55 publications

Chiral Macroheterocycles as Inducers of Helical Liquid Crystals: Molecular Design, Specialty of Functioning

Chiral Macroheterocycles as Inducers of Helical Liquid Crystals: Molecular Design, Specialty of Functioning

Main Strategies for the Synthesis of meso-Arylporphyrins

Mechanisms of Chiral Transfer in Optically Active Dopant – Nematic Liquid Crystal Systems

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