Organic non-linear optical chromophore compound containing 1,3-dithio cyclopentenyl group

A technology based on dithiocyclopentenyl and nonlinear light, which is applied to the application field of the above-mentioned compounds in polarized polymers, and can solve the problems of decreased polarization efficiency, smaller average orientation factor of chromophore molecules, and reduced color development. Problems such as the ground state dipole moment of cluster molecules

Inactive Publication Date: 2005-08-03
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ground state dipole moment of the chromophore molecules is reduced, which will inevitably lead to a decrease in the polarization efficiency, so that the average orientation factor of the chromophore molecules becomes smaller

Method used

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  • Organic non-linear optical chromophore compound containing 1,3-dithio cyclopentenyl group
  • Organic non-linear optical chromophore compound containing 1,3-dithio cyclopentenyl group
  • Organic non-linear optical chromophore compound containing 1,3-dithio cyclopentenyl group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of Organic Chromophore Compound 4-(2,5,7,9-tetrathiobicyclo[4.3.0]-nonenylene)-4'-(fluorenylene)styrenebenzene (1)

[0037]

[0038] 1) 2,5,7,9-tetrathiobicyclo[4.3.0]-nonene-1(6)-8-triphenylphosphonium salt (2) Synthesis with reference to literature (A.J.Moore, M.R.Bryce, synthesis, 26 -28, 1990). MS (TOF): 454 (M-1).

[0039]

[0040] 2) Synthesis of p-fluorenylidene toluene (3):

[0041]

[0042] in N 2 Under atmosphere, add 30mL of freshly steamed absolute ethanol to a 100mL three-necked round-bottomed flask containing an electromagnetic stirrer, and then add 1.00g of Na metal cut into small pieces. After the reaction of Na was completed, 3.32 g of fluorene was added thereto under stirring. Heat to 50°C, then add 3.00g p-tolualdehyde / 10mL absolute ethanol solution. Reaction at this temperature for 6h, cooled to room temperature. The solid was collected by filtration to obtain 3.46 g of a yellow solid, and the product was pure enough to direc...

Embodiment 2

[0052] Synthesis of Organic Chromophore Compound 2-(2,5,7,9-tetrathiobicyclo[4.3.0]-nonenylene)-5-[p-fluorenylenestyryl]thiophene (6)

[0053]

[0054] 1) Synthesis of 2-(2,5,7,9-tetrathiobicyclo[4.3.0]-nonenylidene-1(6)-8-yl)-5-thiophenecarbaldehyde (7):

[0055]

[0056] in N 2 Under protection, 1.60 g of the phosphonium salt 2 synthesized in Example 1 above, 0.14 g of thiophene dicarbaldehyde were added to a 100 mL three-neck round bottom flask, and then 30 mL of freshly steamed tetrahydrofuran and excess triethylamine were added. The reaction was stirred at room temperature for 16 h, the solvent was spin-dried, and the obtained substance was dissolved in dichloromethane, washed with water and saturated brine respectively, and anhydrous MgSO 4 After drying overnight, remove the desiccant, spin dry and separate by column chromatography. 0.266 g of a yellow solid substance was obtained. MS (EI): 316 (M + ), 288, 168.

[0057] 2) Synthesis of compound 6:

[0058] i...

Embodiment 3

[0060] Synthesis of Organic Chromophore Compound 4-(2,5,7,9-tetrathiobicyclo[4.3.0]-nonenylene)-4'-(fluorenylidene)benzylidene (8)

[0061]

[0062] 1) Synthesis of 4-fluorenylidene-4'-nitrobenzene (9)

[0063]

[0064] in N 2 Under the atmosphere, add 20 mL of freshly steamed absolute ethanol to a 100 mL three-neck round-bottomed flask containing an electromagnetic stirrer, and then add 0.28 g of Na metal cut into small pieces. After the Na reaction is complete, add 1.00g fluorene to it under stirring, heat to 50°C, then add 0.91g p-nitrobenzaldehyde / 20mL absolute ethanol solution, react at 50°C for 6h, cool, and filter to obtain yellow slightly Red solid substance 0.46g, MS (HR-EI): 299.0952 (M + ) (Cal. 299.0946).

[0065] 2) Synthesis of p-fluorenylidene aniline (10)

[0066]

[0067] In a 100mL three-necked round-bottom flask, add 0.90g of the above-mentioned synthesized 9 and 50mL of absolute ethanol, and add 3.50g of SnCl 2 2H 2 O dissolved in concentrate...

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PUM

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Abstract

The present invention provides a kind of organic nonlinear optical chromophore compound containing 1, 3-dithio cyclopentenyl group. The compound has ground-state dipole moment lower than that of available organic chromophore compound for polarized polymer. It has exocylic double bond connected to its 1, 3-dithio cyclopentenyl group and constituting one part of molecular conjugated bridge bond, and has molecular ground-state dipole moment of 2-6.5 D, molecular first order hyperpolarizability beta higher than that of p-nitraniline, and excellent transparency and heat stability.

Description

technical field [0001] The invention relates to an organic nonlinear optical chromophore compound containing 1,3-dithiocyclopentenyl. [0002] The present invention also relates to the use of the above compounds in polarized polymers. Background technique [0003] Nonlinear optical materials and devices are one of the key materials for the development of optoelectronic technology. Since the advent of lasers in the 1960s, especially the great progress in the molecular engineering of organic nonlinear optics in the mid-1970s, organic nonlinear optical materials have become one of the most popular materials in the field of nonlinear optics. The morphology of organic second-order nonlinear optical materials mainly includes single crystal, polarized polymer film, LB film, self-assembled film, organic-inorganic hybrid film, etc. From practical considerations, polarized polymer film is the most suitable. The basic condition for a material to exhibit a second-order nonlinear optic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/06C08K5/45
Inventor 秦安军叶成白凤莲
Owner INST OF CHEM CHINESE ACAD OF SCI
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