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Fluorene derivatives having multi-photon absorption characteristic, synthesis method and applications thereof

A multi-photon absorption and synthesis method technology, which is applied in the field of fluorene derivatives with three-photon absorption characteristics and its preparation, can solve the problems that three-photon absorption materials are rarely reported, and achieve reasonable design, high stability, multi-photon absorption The effect of large cross-section

Inactive Publication Date: 2013-06-05
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, the stability of picosecond lasers is worse, but there are few reports on three-photon absorbing materials that achieve stable amplitude for picosecond lasers or lasers with shorter pulse widths

Method used

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  • Fluorene derivatives having multi-photon absorption characteristic, synthesis method and applications thereof
  • Fluorene derivatives having multi-photon absorption characteristic, synthesis method and applications thereof
  • Fluorene derivatives having multi-photon absorption characteristic, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis steps of 2,7-bis(4-methoxyphenylacetylene)-9-thione fluorene:

[0029] (1) Mix 2.5mmol potassium hydroxide and 200mmol fluorene into a beaker, gradually add 55°C dimethyl sulfoxide and stir until it is completely dissolved, keep the solution temperature at 55°C, pass in air, stir for 4 hours, and then react The solution was poured into water (the amount of water was 3 times the volume of the solution), and a yellow precipitate was precipitated, which was filtered, washed, dried, and recrystallized in ethanol to obtain 9-fluorenone with a yield of 83%;

[0030] (2) Mix 50mmol of fluorenone and 0.15mmol of iodine, add it to 80mL of water, slowly add 120mmol of bromine dropwise while stirring, heat and reflux for 7 hours, after the reaction is completed, wash with saturated aqueous sodium bisulfite until the red color fades, and then Washed 4 times with distilled water and recrystallized in ethanol to obtain 2,7-dibromofluorenone with a yield of 55%;

[0031...

Embodiment 2

[0034] The synthetic method of 2,7-bis(4-methoxyphenylacetylene)-9-thione fluorene is the same as that in Example 1, except that the ratio of raw materials and reaction conditions in each step are as follows:

[0035] (1) 2mmol potassium hydroxide and 200mmol fluorene were mixed and put into a beaker, the reaction temperature was 40°C, and after stirring for 5 hours, the yield was 75%;

[0036] (2) Add 50mmol fluorenone and 0.13mmol iodine to 90mL water, add 150mmol bromine dropwise, heat and reflux for 15 hours, yield 50%;

[0037] (3) Add 2.5mmol Pd(OAc) to a reaction flask 2 , 5mmolPPH 3、 150mL mixed solution of water and acetonitrile (volume ratio 1:8); add 20mmol 2,7-dibromofluorenone, 50mmol 4-methoxyphenylacetylene, 50mmol Bu 4 NHSO 4 , 300mmol triethylamine, 150mL mixed solution of water and acetonitrile (volume ratio is 1:8). Reaction at 25°C for 5 hours, yield 50%;

[0038] (4) 5 mmol of 2,7-bis(methoxyphenylacetylene)-9-fluorenone and 10 mmol of Lawson's reagen...

Embodiment 3

[0040] The synthetic method of 2,7-bis(4-n-pentoxyphenylacetylene)-9-thione fluorene is the same as that in Example 1, except that the raw materials, proportioning and reaction conditions in each step are different:

[0041] (1) Mix 3mmol potassium hydroxide and 200mmol fluorene into a beaker, the reaction temperature is 45°C, and after stirring for 5 hours, the yield is 80%;

[0042] (2) Add 50mmol of fluorenone and 0.17mmol of iodine to 90mL of water, add 150mmol of bromine dropwise, heat and reflux for 10 hours, yield 51%;

[0043] (3) 5mmol Pd(OAc) 2 , 5mmol PPH 3 Add a reaction flask, then add 150mL of water and acetonitrile mixed solution (volume ratio is 1:10); add 20mmol 2,7-dibromofluorenone, 50mmol 4-n-pentoxyphenylacetylene, 70 mmol Bu 4 NHSO 4 , 400 mmol triethylamine, and then add 150 mL of a mixed solution of water and acetonitrile (volume ratio is 1:10). Reaction at 30°C for 10 hours, yield 85%;

[0044] (4) 5 mmol of 2,7-bis(4-n-pentyloxyphenylacetylene)-...

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Abstract

The present invention provides fluorene derivatives having a multi-photon absorption characteristic, a preparation method and applications thereof. According to the preparation method, fluorene is adopted as a raw material, potassium hydroxide is adopted as a catalyst, oxidation is performed to prepare 9-fluorenone, a bromination reaction is adopted to link bromine to the fluorene ring, the obtained compound and phenylacetylene containing an ether group (-O-R) generate a fluorenone derivative under an effect of the catalyst, and the fluorenone derivative reacts with a Lawesson reagent to generate a series of fluorene derivative materials having a multi-photon absorption characteristic, wherein the method has characteristics of mild conditions, high reaction selectivity and low cost. The materials can be used in ultrafast laser amplitude stabilizers.

Description

technical field [0001] The invention relates to multi-photon absorption, in particular to a fluorene derivative with three-photon absorption characteristics and its preparation method and application. Background technique [0002] Maria in 1931 -Mayer predicted the existence of multiphoton absorption in his doctoral dissertation. Thirty years later, due to the emergence of lasers, people observed the phenomenon of multiphoton absorption for the first time. Multiphoton absorption refers to the simultaneous absorption of multiple photons by a medium to transition to a higher energy level. References: [1] -Mayer M., Ann. Phys, 1931, 9:275-294. Because multiphoton absorption has many excellent properties, such as large penetration depth, small linear absorption and scattering loss, high damage threshold, nonlinear response characteristics, etc., multiphoton absorption can be widely used in three-dimensional optical information storage. References: [2] B.H.Cumpston et al.Nat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/243C07C41/01G02F1/35
Inventor 刘军辉王渊旭李国凤
Owner HENAN UNIVERSITY
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