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Metal organic liquid crystal dyes

A liquid crystal, metal technology, applied in the field of dye components, polymer dispersed liquid crystal, can solve the problem of uneven projection spectrum of metal organic mesogen composition

Inactive Publication Date: 2017-11-28
GAUZY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Inhomogeneous projection spectra of metal-organic mesogenic compositions

Method used

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  • Metal organic liquid crystal dyes
  • Metal organic liquid crystal dyes
  • Metal organic liquid crystal dyes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0189] Synthesis of HL2 Ligand: C22H28N2O

[0190] The synthesis of the HL2 ligand C22H28N2O was obtained by diazotization of 4-hexylaniline. Subsequent coupling with phenol affords 4-hydroxy-4'-hexylazobenzene (I) and etherification with 4-bromo-1-butene as shown in the following scheme:

[0191]

[0192] 8.5 mmol (1.5 g) of 4-hexylaniline were dissolved in 8 mL of water and 2.1 mL of HCl (36%) under nitrogen. The solution was cooled at 0°C, and 8 mL of aqueous NaNO2 (0.6 g, 9.1 mmol) was added, keeping the solution temperature below 5°C. Phenol (0.8 g, 8.5 mmol) dissolved in 2.5 mL NaOH 2N was added dropwise to the solution of the diazonium salt. The reaction mixture was warmed to room temperature and extracted with dichloromethane; the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product I was purified by chromatography (silica gel, hexane / ether, 1 / 1) and recrystallized from n-heptane to give the pure product a...

Embodiment 2

[0203] Synthesis of Metal Mesogenic Complex L2Pd-acac(C27H34N2O3-Pd)

[0204] The synthesis of metal-mesomorphic (MOM) C27H34N2O3-Pd complex is accomplished through the following two-step reaction:

[0205]

[0206] First, the ring-palladiumation of the ligand 4-(3-butenyloxy)-4'-hexylazobenzene 4 with [(PhCN)2PdC12] gave the dinuclear chlorine-bridged derivative [LPd(μ-Cl) ]2, then obtained as a mixture of isomers of A and B complexes by a bridge-splitting reaction with ethyl-pyruvate potassium complex 5 in a molar ratio of 2:1, composed of two Obtained by non-selective precipitation of the benzene ring. To a suspension of 0.1 g of 4 in methanol (5 mL) was added an equimolar amount of [Pd(PhCN)Cl]2 (0.11 g) dissolved in 6 mL of benzene. The mixture was stirred at room temperature for 24 h and the brown solid formed was filtered off and recrystallized from dichloromethane / ethanol to give the pure product [LPd(μ-Cl)]2 as an ocher yellow solid in 83% yield ( 0.12G). In a ...

Embodiment -3

[0218] Synthesis of a one-pot chemical mixture of salicylic acid diamine metal mesogens

[0219] Complex

[0220] "One-pot" solution synthesis: The synthesis of "one-pot" multi-component metal mesomorphic mixtures based on salicylic acid diamine metal complexes proceeds by the simultaneous reaction of suitable precursors, as in the single-component metal Synthesis in mesogens. Each "in situ" mixture consists of a three-component system corresponding to the following general chemical structure:

[0221]

[0222] Two heterofunctional linkage (two aldehydes) molecules react simultaneously with amines and finally with metal ions. Although only two heterofunctional groups (aldehydes and / or amines) are used, simultaneous synthesis of more than two heterofunctional species can provide an increasing number of structurally distinct metal complexes. Six three-component "in situ" metallo-mesomorphic mixtures were prepared under various combinations of metals and ligands. Each comp...

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Abstract

A dye composition dissolvable within a liquid crystal host device (including: polymer dispersed liquid crystal, polymer network liquid crystal, polymer stabilized liquid crystal, liquid crystal displays and similar devices), comprising eutectic mixtures of dichroic metallomesogen molecules. The aforesaid metallomesogen molecules comprise chromophore groups synthesized by physical and chemical mixing methods.

Description

technical field [0001] The present invention relates to liquid crystal devices, in particular to polymer dispersed liquid crystals, and more specifically to dye components. Background technique [0002] US patent application US5843333A discloses a polymer dispersed liquid crystal electro-optical device composite material comprising a polymer continuous phase and a discontinuous liquid crystal phase comprising metal organic mesogens. The continuous phase is a thermoset or thermoplastic polymer composition. The discontinuous phase may also comprise a host-guest system consisting of an organic liquid crystal host compatible with the dichroic metal-organic mesogen guest. [0003] The cast spectrum of metal-organic mesogenic compositions is not uniform. Specifically, in the blue near ultraviolet range, the dichroic metal-organic mesogen composition has higher light transmittance. Thus, there is a longstanding and unmet need to provide metallomesogen compositions with controlla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/54
CPCC09B23/148C09B45/22C09B55/001C09B55/005C09B57/10C09K19/40C09K19/60C09K19/605C09B55/002G02F1/1334G02F2202/04
Inventor 哈桑·阿里·哈科密艾德里安·洛弗埃亚勒·比索
Owner GAUZY
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