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Two-dimensional spindly non-linear optic chromophore molecule

A nonlinear optical and spindle-shaped technology, applied in organic chemistry, luminescent materials, chemical instruments and methods, etc., can solve the problems of low phase matching ability, small rotation radius, etc., and achieve the effect of improving the stability of nonlinear optics

Inactive Publication Date: 2011-10-19
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, one-dimensional chromophore molecules exhibit low phase matching ability due to their small gyration radius

Method used

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  • Two-dimensional spindly non-linear optic chromophore molecule
  • Two-dimensional spindly non-linear optic chromophore molecule
  • Two-dimensional spindly non-linear optic chromophore molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The synthetic route of the two-dimensional spindle-shaped chromophore molecule is as follows:

[0059]

[0060] Synthesis of [1,1'; 4',1"]terphenyl-2',5'-dialdehyde

[0061] The compound triphenylphosphine (0.015g, 0.06mmol), palladium acetate (0.002g, 0.01mol), phenylboronic acid (0.24g, 2mmol), 2,5-dibromo-1,4-terephthalaldehyde (0.29 g, 1mmol) of the mixture was added to a 100ml three-necked flask, and nitrogen protection was introduced. Then isopropanol (10ml), 2N / L sodium carbonate solution (3ml) and water (1ml) were transferred to the flask, stirred, and the reaction system was heated to 70°C for 4 hours. After extraction with dichloromethane, wash once with saturated sodium bicarbonate solution, concentrate and dry under vacuum to obtain a light yellow solid. Purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1:30) to obtain 0.25 g of white crystals with a yield of 95%. 1 HNMR (500MHz, CDCl 3 , TMS): δ (ppm) 7.44-7.46 (d, 4H, J ~ 9...

Embodiment 2

[0068]

[0069] Synthesis of 2,5-(3,4,5-trifluorophenyl)-1,4-dicarbaldehyde:

[0070] 2,5-dibromobenzene-1,4-dicarbaldehyde (0.5g, 1.72mmol) and 3,4,5-trifluorophenylboronic acid (0.596g, 4.11mmol) were dissolved in tetrahydrofuran (15mL), and nitrogen gas Protect. Add palladium acetate (6mg, 0.026mmol) to the solution, triphenylphosphine (20.52mg, 0.078mmol), 2M sodium carbonate (15.3mL, 40mmol), deionized water (14mL), heat to reflux, and React for 6 hours. The layer was concentrated under reduced pressure and purified by column chromatography with petroleum ether-ethyl acetate (20:1) as the eluent to obtain 0.4 g (60%) of a yellow solid.

[0071] Synthesis of 2,5-(3,4,5-trifluorophenyl)-4-(4-(dimethylamino)styryl)benzaldehyde:

[0072] 2,5-(3,4,5-trifluorophenyl)-1,4-dicarbaldehyde (0.4g, 1.02mmol) was dissolved in 20mL of dichloromethane, and then iodide (4-dimethyl Amino-benzylidene)-triphenylphosphonium salt (0.532g, 1.02mmol) and potassium tert-butoxide (0.172g, ...

Embodiment 3

[0077] Synthesis of [1,1'; 4',1"]terphenyl-2',5'-dialdehyde

[0078] Same as Example 1

[0079] Synthesis of 2-[4-(N,N-dimethylamino)styryl]-1,4-diphenylbenzaldehyde

[0080] Same as Example 1

[0081] Synthesis of 2-[4-(N,N-dimethylamino)styryl]-1,4-diphenylstyryltricyanoethenyl-2,2-dimethyldihydrofuran

[0082] Dissolve 2-[4-(N,N-dimethylamino)styryl]-1,4-diphenylbenzaldehyde (0.52 g, 1 mmol) in dry THF (3 ml), then add tricyano Vinyl-1-methyldihydrofuran (0.2g, 1.0mmol) and piperidine (0.03ml), the reaction system was stirred at room temperature for 2 hours, and the temperature was raised to 90°C to continue the reaction for 2 hours. A purple solution was obtained. The progress of the reaction was monitored by TLC. After the reaction was completed, it was washed with water, extracted three times with dichloromethane, and a red solid was obtained after the solvent was concentrated. The crude product was purified by column chromatography (petroleum ether: ethyl acetate =...

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PUM

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Abstract

The invention belongs to the technical field of high molecular materials, and particularly relates to a series of novel two-dimensional spindly non-linear optic chromophore molecules which take terphenyl or triheteroaromatic compounds as conjugated bridges. The series of chromophore molecules have good thermodynamic stability and non-linear optic properties. The chromophore molecule takes terphenyl or triheteroaromatic compounds as conjugated bridge, triphenylamine or tricyano-dihydro furan (TCF) as electron donors and 1,3,3-trimethyl-5-dicyanovinyl-1-cyclohexane (TDC) as electron acceptors, and the synthesized chromophore molecule has good thermostability. The structure of the chromophore has terphenyl group or triheteroaromatic group, and the geometric construction of the chromophore is approximately spherical, and the prepared polarized non-linear optic membrane has good thermostability and time stability.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a series of novel two-dimensional spindle-shaped nonlinear optical chromophore molecules with terphenyl or terphenyl aromatic heterocyclic compounds as conjugate bridges. The series of chromophore molecules have Good thermodynamic stability and nonlinear optical properties. Background technique [0002] The application of electro-optic materials in optoelectronic devices has potential application value in optical communication and optical information processing. Usually, the second-order nonlinear optical chromophore molecules are doped with the host polymer or bonded to the polymer skeleton to prepare optoelectronic materials. device. A necessary condition for second-order nonlinear effects is that the material has structural noncentrosymmetry, which is achieved by orienting the chromophore molecules along the direction of the electric field with an applie...

Claims

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Application Information

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IPC IPC(8): C07C255/31C07C253/30C07D307/68C07D333/24C09K11/06
Inventor 崔占臣史作森张晓龙赵莉莎李明
Owner JILIN UNIV
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