Symmetric discotic pyrene compounds and preparation method thereof

A compound and symmetrical technology, applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of carboxylic acid nitriles, etc.

Inactive Publication Date: 2012-06-20
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Symmetric discotic pyrene compounds and preparation method thereof
  • Symmetric discotic pyrene compounds and preparation method thereof
  • Symmetric discotic pyrene compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: synthetic compound:

[0032]

[0033] with R 1 structured as , R 2 structured as

[0034] The synthetic method of this compound is introduced as an example

[0035] 1: Bromination reaction of pyrene: Dissolve 24.72 mmol pyrene (5.00g) in 250 mL nitrobenzene solution, put it in a 500 mL single-necked flask (with a magnetic stirrer), add excess bromine dropwise to it , the silicone oil bath was raised to 140 degrees Celsius, and the reflux reaction was carried out for 10 hours. After the product is cooled, pour it into dilute sodium bisulfite solution and stir to remove bromine, and change the water every ten minutes until the solution is colorless. The water layer was removed by liquid separation, ethanol was added to the organic layer to continue stirring, suction filtered three times, and then filtered three times with dichloromethane. The filtered product was placed in a vacuum drying oven, and dried to obtain 11.60 g of a light green solid ...

Embodiment 2

[0043] Synthetic compound:

[0044] with R 1 structured as , R 2 structured as The synthetic method of this compound is introduced as an example

[0045] 1: Bromination reaction of pyrene: Dissolve 24.72 mmol pyrene (5.00g) in 250 mL nitrobenzene solution, put it in a 500 mL single-necked flask (with a magnetic stirrer), add excess bromine dropwise to it , the silicone oil bath was raised to 140 degrees Celsius, and the reflux reaction was carried out for 10 hours. After the product is cooled, pour it into dilute sodium bisulfite solution and stir to remove bromine, and change the water every ten minutes until the solution is colorless. The water layer was removed by liquid separation, ethanol was added to the organic layer to continue stirring, suction filtered three times, and then filtered three times with dichloromethane. The filtered product was placed in a vacuum drying oven, and dried to obtain 11.60 g of a light green solid with a yield of 91%.

[0046] 2: ...

Embodiment 3 and 4

[0053]

[0054]

[0055] raw material product Example 3 Example 4 Tetrabromopyrene 0.64g (1.24mM) 0.64g (1.24mM) Trimethylsilylacetylene (TMSA) 0.95g (9.67mM) 0.95g (9.67mM) Dibutyl-p-iodoaniline 2.46g (7.44mM) 2.46g (7.44mM) F4-TCNQ 0.96 g (3.47 mM) —— TTF —— 0.71 g (3.47 mM)

[0056] The final obtained Example 3 was 1.29 g, and Example 4 was 1.07 g.

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Abstract

The invention belongs to the technical field of organic synthesis and relates to symmetric discotic pyrene compounds and a preparation method of the symmetric discotic pyrene compounds. The compounds have the following general formula, wherein R1 and R2 are the same or R1 is H and R2 is C1-C20 p-acetylene-dialkyl phenylamine, triazoles or conjugated butadiene phenylamines. The preparation method of the compounds comprises the following steps of: bromination of pyrene, Sonogashira coupling reaction, de-trimethylsilyl reaction, bromide chain grafting reaction and click chemistry reaction. The symmetric discotic pyrene compounds prepared by the invention have a strong discotic conjugation structure and strong electron-withdrawing groups, so that the compounds have good nonlinear optical effects. Besides, owing to the strong side chain modifiability, the compounds can be grafted with different conjugate groups and chromophoric groups, to provide great support for preparing novel nonlinear optical materials. Therefore, the compounds have great potential application values.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a non-linear optical material pyrene-type symmetrical disc compound and a preparation method thereof. Background technique [0002] Nonlinear optical materials are an important material basis for photonic technology, and can be widely used in optical communication, optical computing, optical information processing, optical storage, optical holography, laser processing, laser film and television and other fields. Its development has become one of the main symbols to measure the level of science and technology of a country. [0003] Compared with inorganic nonlinear crystal materials, organic nonlinear crystal materials have the following advantages: (1) faster response time (sub-picosecond level); (2) larger nonlinear coefficient (usually 1 to 2 orders of magnitude higher than that of inorganic crystals) ; ⑶ high light damage threshold; ⑷ small dielectric constant; ⑸ ease...

Claims

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Application Information

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IPC IPC(8): C07C255/42C07C253/00C07D339/06
Inventor 杨槐金召奎王冬杜政才梁蓬霞弥永胜
Owner UNIV OF SCI & TECH BEIJING
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