N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole and preparation method thereof

A vinyl, methyl quinoline technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of poor thermal stability and photochemical stability, and achieve good photochemical stability, good thermal stability and The effect of photochemical stability and good thermal stability

Inactive Publication Date: 2012-08-15
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented compound allows for better control over how light emitted from certain materials interact with each other when exposed to different types of radiation such as X ray or gamma ray. Its properties make them useful in various applications like displays, sensors, detectors, biological probes, imagers, solar cells, batteries, phosphorus pigments, chemical reactions, catalysts, dyes, polymers, plasma display screens, medical diagnostic devices, nanoelectronics, optofluidic systems, and others.

Problems solved by technology

This patented technical problem addressed by this patents relates to finding ways to improve both properties (thermal or photochemistry) of certain types of material that can absorb light simultaneously when exposed to high levels of energy during an interaction between different states without losing their ability to change color swiftly.

Method used

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  • N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole and preparation method thereof
  • N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole and preparation method thereof
  • N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole and preparation method thereof

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specific Embodiment approach 1

[0026] Specific embodiment one: the N-alkyl-3 of the present embodiment, the structural formula of 6-two [(2-quinoline) vinyl] carbazole is as follows:

[0027]

[0028] Among them, R is C n h 2n+1 Or benzyl, n is 1-8.

[0029] The N-alkyl-3,6-bis[(2-quinoline)vinyl]carbazole of the present embodiment is that the electron acceptor group is connected to both sides of the carbazole ring at the 3,6 position, and the 3, 6-diformyl-N-alkyl-carbazole derivatives and 2-methylquinoline are produced by Knoevenagel Reaction under the condition of acetic anhydride as condensing agent. It can produce fluorescence phenomenon under the irradiation conditions of 365nm of ordinary 8 watts and 254nm low-energy ultraviolet wavelength of 6 watts, and the N-alkyl-3,6-bis[(2-quinoline)ethylene of this embodiment Base] carbazole has good thermal stability and photochemical stability, and can undergo two-photon absorption phenomenon under 800nm ​​femtosecond laser, and can be excited to produce f

specific Embodiment approach 2

[0030] Specific embodiment two: N-alkyl-3 of the present embodiment, the preparation method of 6-two [(2-quinoline) vinyl] carbazole is carried out according to the following steps: 1. Weigh 1% by mass percentage ~3% of 3,6-diformyl N-alkyl-carbazole, 5%~7% of 2-methylquinoline and 90%~94% of acetic anhydride; , mix 6-diformyl-N-alkyl-carbazole and 2-methylquinoline evenly, then add the acetic anhydride weighed in step 1, stir evenly, heat to 100°C~140°C, and keep for 24~ 72h, cooled to room temperature to obtain the reaction solution; 3. Mix the reaction solution obtained in step 2 with water in a volume ratio of 1:2 to obtain the initial mixed solution; then use a concentration of 10-25mol / L alkaline The solution adjusts the pH value of the initial mixed solution to 7.0 to obtain a mixed solution; 4. Extract the mixed solution obtained in step 3 with dichloromethane, collect the extract, and use a rotary evaporator to store the extract at a temperature of 50°C to 70°C Carry

specific Embodiment approach 3

[0034] Embodiment 3: This embodiment is different from Embodiment 2 in that: the water described in step 3 is pure water. Others are the same as in the second embodiment.

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Abstract

N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole and a preparation method thereof relate to carbazole derivatives and preparation methods thereof and aim to solve the problems of poor thermal stability and photochemical stability of existing two-photon absorption materials. The structural formula of the N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole is shown as follow, wherein the R is CnH2n+1 or benzyl, and the n ranges from 1 to 8. The preparation method of the N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole includes: firstly, mixing 3, 6-dimethyl acyl-N-alkyl-carbazole, 2-methyl quinoline and acetic anhydride uniformly, then mixing with water uniformly and regulating the pH (potential of hydrogen) value to be 7.0; and secondly, extracting by dichloromethane, collecting extract and obtaining the N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole. The carbazole derivatives of the N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole have two-photon absorption function and fine dissolubility, thermal stability and photochemical stability. The N-alkyl group-3, 6-di-(2-quinoline) vinyl) carbazole can be applied to the technical field of two-photon absorption materials.

Description

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Claims

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Application Information

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Owner HEILONGJIANG UNIV
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