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Organic second-order non-linear optical chromophore with D-Pi-A structure and decorated by tree-like group, synthesizing method and application thereof

A second-order nonlinear and dendritic technology, which is applied in the field of organic second-order nonlinear optical chromophores and their synthesis, can solve the problems of small electro-optical coefficients, inability to meet the requirements of deviceization, and low polarization efficiency.

Inactive Publication Date: 2012-05-30
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A series of chromophores containing pyrroline electron acceptors reported in Chem.Mater., Vol.18, No.13, 2006 and US Patent No. 7307173B1 have higher first-order molecular hyperpolarizability, but these chromophores Due to the large intermolecular interaction force in the polymer, the polarization efficiency is not high, and the electro-optical coefficient is small, which cannot meet the requirements of deviceization.

Method used

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  • Organic second-order non-linear optical chromophore with D-Pi-A structure and decorated by tree-like group, synthesizing method and application thereof
  • Organic second-order non-linear optical chromophore with D-Pi-A structure and decorated by tree-like group, synthesizing method and application thereof
  • Organic second-order non-linear optical chromophore with D-Pi-A structure and decorated by tree-like group, synthesizing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of dendrimer-modified chromophores with D-π-A structure as shown below

[0042]

[0043] The synthetic route is as follows:

[0044]

[0045] Among them, Me is methyl, PPh 3 is triphenylphosphine, TBDMSCl is tert-butyldimethylsilyl chloride, and TCP is a tricyanopyrroline electron acceptor, and its structure is:

[0046]

[0047] The synthesis method is:

[0048] 1) Synthesis of Compound 2

[0049] Get 4g (0.0064mol) bromo-3,4-dihexyloxythienyltriphenylphosphine, 1.9g (0.0064mol) acetyl protected 4-(N,N-dihydroxyethyl)aminobenzaldehyde Electron donor, 4.6g (0.192mol) sodium hydride (NaH) mixed in 100ml of anhydrous ether solvent, stirred at 50 ° C for 18 hours, the reaction product was poured into 200ml of ice water, separated, ether extracted the water phase, combined The organic phase was dried with anhydrous magnesium sulfate, filtered, and the ether was removed by rotary evaporation to obtain a brown-red viscous substance, which was separated ...

Embodiment 2

[0062] Synthesis of dendrimer-modified chromophores with D-π-A structure as shown below

[0063]

[0064] The synthetic route is as follows:

[0065]

[0066] Among them, PPh 3 It is triphenylphosphine, TCP is tricyanopyrroline electron acceptor, its structure is

[0067]

[0068] The synthesis method is:

[0069] 1) Synthesis of Compound 2

[0070] Get 4g (0.0064mol) bromo-3,4-dihexyloxythienyltriphenylphosphine, 1.1g (0.0064mol) 4-(N,N-diethyl)aminobenzaldehyde electron donor, 2.3 g (0.096mol) of sodium hydride (NaH) was mixed in 100ml of anhydrous ether solvent, and after stirring at 20°C for 50 hours, the reaction product was poured into 200ml of ice water, separated, the aqueous phase was extracted with ether, the organic phase was combined, and Dry the organic phase with anhydrous magnesium sulfate, filter, and remove ether by rotary evaporation to obtain a red sticky substance, which is separated by column chromatography (stationary phase is 200-300 mesh si...

Embodiment 3

[0078] Synthesis of dendrimer-modified chromophores with D-π-A structure as shown below

[0079]

[0080] The synthetic route is as follows:

[0081]

[0082] Among them, Me is methyl, PPh 3 is triphenylphosphine, TBDMSCl is tert-butyldimethylsilyl chloride, and TCP is tricyanopyrroline electron acceptor, its structure is

[0083]

[0084] The synthesis method is:

[0085] 1) Synthesis of Compound 2

[0086] Take 4g (0.0068mol) of bromo-3,4-dibutoxythienyltriphenylphosphine, 1.5g (0.0068mol) of acetyl-protected 4-(N-methyl, N-hydroxyethyl)amino Benzaldehyde electron donor and 4.1g (0.17mol) sodium hydride (NaH) were mixed in 100ml of anhydrous ether solvent, stirred at 40°C for 24 hours, the reaction product was poured into 200ml of ice water, separated, and the aqueous phase was extracted with ether , combine the organic phases, dry the organic phases with anhydrous magnesium sulfate, filter, and remove ether by rotary evaporation to obtain a brown-red viscous su...

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Abstract

The invention relates to an organic second-order non-linear optical chromophore with a D-Pi-A structure and decorated by a tree-like group, and a synthesizing method and applications thereof. The chromophore of the invention introduces a thiophene ring conjugated Pi electronbridge having stronger electrical transmission capacity and containing branched chains and a tricyano pyrroline receptor having strong electron-withdrawing property; the receptor end is introduced into the tree-like decorative group, the one-order hyperpolarizability of chromophore molecules is greatly improved; the solubility and the film forming ability of the chromophore in polymer is improved, the interaction force among the molecules is reduced. The second-order non-linear optical chromophore with the following structure is doped with polymers, such as amorphous polycarbonate or polymethylmethacrylate and the like according to the mass ratio of 1:10; the electro-optical coefficient of the obtained polarized polymeric materials achieves 217pm / V; in addition, the donor and receptor of the chromophore can be introduced into a crosslinkable group, thus improving oriented stability of the chromophore in polymer, and satisfying the requirements of devices.

Description

technical field [0001] The invention relates to the field of organic second-order nonlinear optical materials, in particular to an organic second-order nonlinear optical chromophore with a D-π-A structure modified by a dendritic group with high electro-optic activity and its synthesis method and application . Background technique [0002] In the current society, laser and optical fiber communication are replacing microelectronics and integrated circuit technology and becoming emerging communication technologies. As two cutting-edge disciplines of laser communication and optical fiber communication: integrated optics and optoelectronics have achieved rapid development. The integrated optical system includes important devices such as waveguides, optical switches, and optical converters, and nonlinear optical materials must be used in these devices. At present, the nonlinear optical materials that are widely used in practice are mainly inorganic crystal materials. Compared w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06C07F7/18C08L69/00C08L33/12C08K5/45C08K5/548G02F1/361
Inventor 甄珍冯姝雯刘家磊侯文军邱玲刘新厚
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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