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Fluorene derivative containing large conjugated molecule and preparation thereof

A technology for conjugated molecules and derivatives is applied in the field of fluorene derivatives and their preparation, and achieves the effects of increasing nonlinear optical coefficients, improving solubility and processing performance, and overcoming poor chemical stability.

Inactive Publication Date: 2010-12-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, organic low-molecular-weight crystals have high nonlinear optical coefficients, are easy to purify, and have no structural defects. These advantages cannot be achieved by organic high-molecular polymers. Therefore, inheriting these advantages of organic low-molecular materials, design and develop organic low-molecular non- Linear optical materials are of great significance

Method used

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  • Fluorene derivative containing large conjugated molecule and preparation thereof
  • Fluorene derivative containing large conjugated molecule and preparation thereof
  • Fluorene derivative containing large conjugated molecule and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Add 1g of 2,3,6,7-tetraamino-9,9'-diisooctylfluorene, 3 times the molar amount of phenanthrenequinone and 1 times the molar amount of potassium carbonate to 15mL acetic acid solution, under the protection of nitrogen , Refluxed for 2h, cooled and filtered under reduced pressure to obtain 0.6g of yellow solid. MS: 794.4368; 1 H NMR (400M, CD 3 OD): δ( * 10 -6 )6.79(s, 2H), 6.50(s, 2H), 7.19-7.30(s, 8H), 1.89-1.92(m, 4H, CH 2 ), 1.02-1.08 (m, 4H, CH 2 ), 0.67(t, J(H-H)=7.4MHz, 6H), 0.52-0.63(m, 4H, CH 2 ).

Embodiment 2

[0043]

[0044]Add 1g of 2,3,6,7-tetraamino-9,9'-diisooctylfluorene, 2.5 times the molar amount of 3,6-dinitrophenanthrenequinone and 1 times the molar amount of sodium hydride to 20mL acetic acid solution , under the protection of nitrogen, reflux for 10 h, cooled and filtered under reduced pressure to obtain 0.8 g of yellow solid. MS: 974.3766; 1 H NMR (400M, CD 3 OD): δ( * 10 -6 )6.789(s, 2H), 6.53(s, 2H), 5.17(s, 8H), 1.90-1.93(m, 4H, CH 2 ), 1.28-1.33 (m, 20H, CH2), 1.20-1.25 (m, 46H, CH 2 ), 0.88(t, J(H-H)=7.3MHz, 6H).

Embodiment 3

[0046]

[0047] Add 1g of 2,3,6,7-tetraamino-9,9'-diisooctylfluorene, 2.2 times the molar amount of 2,7-dicyanophenanthrenequinone and 1.5 times the molar amount of calcium hydride to 15mL propionic acid The solution was refluxed for 20 h under the protection of nitrogen, cooled and filtered under reduced pressure to obtain 0.55 g of a yellow solid. MS: 894.4168; 1 H NMR (400M, CD 3 OD): δ( * 10 -6 )6.79(s, 2H), 6.50(s, 2H), 5.19(s, 8H), 1.84-1.89(m, 4H, CH 2 ), 1.62-1.70 (d, J=(H-H)=7.4MHz, 1H), 0.91 (d, J(H-H)=7.2MHz, 12H).

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Abstract

The invention relates to a fluorene derivative containing macro conjugated molecules and a method for preparing the same. The macro conjugated molecule fluorene derivative has 2, 3, 6, 7-tetraamino-9, 9'-dialkyl fluorene as a raw material which is added to an organic solvent respectively together with phenanthrenequinone, acenaphthene quinone or bis-carbonyl pyrene derivatives and strong base; under the protection of inert gas, reflux reaction is carried out to the materials, so as to prepare a series of trapezoidal conjugated molecules containing fluorine structures. Alkyl surrounding the molecules helps to overcome solubility reduction caused by the high-plane rigid structure of the molecules, which improves the dissolution processing performance of material molecules. Meanwhile, the conjugation of pi electrons on a skeleton of the trapezoidal conjugated molecules is intensified further, which can reduce the energy gaps of the molecules, increase the nonlinear optical coefficients of the molecules remarkably, play a certain role in overcoming the disadvantages that the prior organic nonlinear micromolecule material is poor in chemical stability and mechanical strength, etc. The fluorene derivative can be widely applied to the organic nonlinear optical material field.

Description

technical field [0001] The invention relates to a class of fluorene derivatives containing large conjugated molecules and a preparation method thereof, belonging to the fields of the preparation of such molecules and the application of organic nonlinear optics. Background technique [0002] With the development of laser technology, the study of nonlinear optical materials (NLO materials), which is an important material basis of laser technology, has become a hot spot in contemporary high-tech research. In recent years, the research of organic nonlinear optical materials is a very active field. The main reason is that some organic materials have much larger nonlinear polarizability (hyperpolarizability, nonlinear optical coefficient) than inorganic materials, and thus are more promising nonlinear optical materials. [0003] In 1964, P.M.Rentzepis et al. and G.H.Heilmeyer observed the second harmonic generation (SHG) of the ruby ​​Nd:Yag laser with 3,4-benzopyrene, 1,2-benzan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06
Inventor 肖义张大奎李熙川
Owner DALIAN UNIV OF TECH
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