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Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof

An induced luminescence, two-photon technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problem of reducing the luminous efficiency of compounds, and achieve the effect of simple doping method, high transparency, and overcoming the easy occurrence of embrittlement.

Active Publication Date: 2012-05-30
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the rotation of the amine group will cause the reduction of the luminous efficiency of the compound to varying degrees (Entwistle C.D., Marder, T.B., Chem.Mater., 2004, 16, 4574)

Method used

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  • Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof
  • Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof
  • Two-photon induced luminous compound with symmetrical both ends and synthesis method and purposes thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] To dissolve 2.96 g (7.2 mmol) of 2,5-dimethoxy-1,4-bis(diethoxyphosphoryl)methyl-benzene in 50 ml of redistilled N,N-dimethylformamide ( DMF) solution, add 2.38 grams (44.0mmol) sodium methylate, after stirring for 20 minutes, add 3.44 grams (16.0mmol) 1,2,2,4-tetramethyl-1,2-dihydro-6-formylquinone Phenyl, react at room temperature for 1.5 hours, then pour the product solution into water and filter. The filter residue was filtered with hot ethanol below the boiling point, and then separated by silica gel column chromatography (eluent: dichloromethane / cyclohexane=100 / 20, v / v), the solvent was removed by rotary evaporation, and the pure product was obtained by vacuum drying. The present invention uses 1,2,2,4-tetramethyl-1,2-dihydro-6-formyl quinoline and 2,5-dimethoxy-1,4-bis(diethoxyphosphoryl ) methyl-benzene as a raw material, the prepared 1,2,2,4-tetramethyldihydroquinoline compound with two-photon induced luminescence characteristic of two-photon symmetry. M.P.23...

Embodiment 2

[0028] Add 2.51 g (46.4 mmol) of sodium methoxide to 2.60 g (7.4 mmol) of 1,4-bis(diethoxyphosphoryl)methyl-benzene in 50 ml of redistilled DMF solution, stir for 25 minutes, then add 3.70 g (17.2 mmol) of 1,2,2,4-tetramethyl-1,2-dihydro-6-formylquinoline were reacted at room temperature for 3 hours, and then the product solution was poured into water and filtered. The filter residue was filtered with hot ethanol below the boiling point, and then separated by silica gel column chromatography (eluent: dichloromethane / cyclohexane=100 / 20, v / v), the solvent was removed by rotary evaporation, and the pure product was obtained by vacuum drying. The present invention uses 1,2,2,4-tetramethyl-1,2-dihydro-6-formyl quinoline and 1,4-bis(diethoxyphosphoryl)methyl-benzene as raw materials to prepare 1,2,2,4-Tetramethyldihydroquinoline compounds with two-photon-induced luminescence characteristics of two-terminal symmetry. 1HNMR (300MHz, CDCl3): δ7.51(s, 4H), 7.33-6.89(m, 8H), 6.53(d, 2H,...

Embodiment 3

[0031] To a solution of 2.95 g (7.8 mmol) of 2,5-dimethyl-1,4-bis(diethoxyphosphoryl)methyl-benzene in 50 mL of redistilled DMF was added 2.72 g (50.4 mmol) of methanol Sodium, after stirring for 30 minutes, add 4.13 grams (19.2mmol) 1,2,2,4-tetramethyl-1,2-dihydro-6-formylquinoline, react at room temperature for 2.0 hours, after that the product solution Pour into water and filter. The filter residue was filtered with hot ethanol below the boiling point, and then separated by silica gel column chromatography (eluent: dichloromethane / cyclohexane=100 / 20, v / v), the solvent was removed by rotary evaporation, and the pure product was obtained by vacuum drying. The present invention uses 1,2,2,4-tetramethyl-1,2-dihydro-6-formyl quinoline and 2,5-dimethyl-1,4-bis(diethoxyphosphoryl) The 1,2,2,4-tetramethyldihydroquinoline compound with two-photon induced luminescence characteristics of two-photon-induced luminescence is produced by using methyl-benzene as a raw material. 1 HNMR (3...

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Abstract

The invention relates to the technical fields of luminous material, two-photon absorption material, optical storage and the like, in particular to two-photon induced luminous compound with symmetrical both ends and a synthesis method and purposes thereof. Raw material sodium methoxide is added into N, N-DMF solvent which is dissolved with phosphate reagent to be uniformly stirred, and then aldehyde is added in to react; the reaction solution is poured into water and filtered; the prepared hot ethanol for residue is filtered; and chromatographic separation is carried out to the rest solid, andthe two-photon induced luminous compound with symmetrical both ends is prepared. After being doped into an epoxy resin solid matrix, the two-photon induced luminous compound with both ends symmetrical prepares strong two-photon induced luminous solid material which can be used for fluorescent probes or fluorescence imaging material. The two-photon induced luminous compound with symmetrical both ends of the invention is a type of two-photon induced luminous 1, 2, 2 and 4-tetramethyl-dihydro-quinoline compound with both ends symmetrical, and the structure of the two-photon induced luminous compound is shown as the accompanying drawing.

Description

technical field [0001] The invention relates to the technical fields of luminescent materials, two-photon absorbing materials and optical storage, and in particular to two-photon-induced luminescent compounds with two-terminal symmetry and their synthesis methods and applications. Background technique [0002] Luminescent materials refer to materials that can emit visible light after being excited by various energies. Such materials have been widely used in high-tech fields such as flat panel displays, lasers, optical lighting, and biomolecular probes. In today's information age, the development of luminescent materials that can meet various information display requirements is particularly rapid. Organic light-emitting materials are mainly composed of organic substances, which have the advantages of easy adjustment of properties through structural modification, easy purification and low cost, and have the advantage of easy large-area film formation. Two-photon induced lumi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/12C09K11/06
Inventor 杨国强李秀平李沙瑜
Owner INST OF CHEM CHINESE ACAD OF SCI
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