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Water-soluble aggregation-induced emission quinoxaline compound, preparation method thereof and application of compound

A technology of aggregation-induced luminescence and quinoxaline, which can be applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., and can solve the problem of rare species of luminescent quinoxalines

Active Publication Date: 2018-09-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of aggregation-induced luminescent quinoxaline with good water solubility and its preparation method and application in view of the scarcity of existing water-soluble aggregation-induced luminescent quinoxalines

Method used

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  • Water-soluble aggregation-induced emission quinoxaline compound, preparation method thereof and application of compound
  • Water-soluble aggregation-induced emission quinoxaline compound, preparation method thereof and application of compound
  • Water-soluble aggregation-induced emission quinoxaline compound, preparation method thereof and application of compound

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Experimental program
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Embodiment 1

[0035]Embodiment 1: Preparation of pyridinium salt quinoxaline compound PQ1

[0036] (1) Preparation of 5,8-dibromo-2,3-bis(4-methoxybenzene)quinoxaline according to literature H.J.Song, D.H.Kim, E.J.Lee, J.R.Haw, D.K.Moon, Sol.Energ.Mat. Prepared by the method disclosed in Sol.C.2014, 123, 112-121.

[0037] (2) Dissolve 10mmol of 5,8-dibromo-2,3-bis(4-methoxybenzene)quinoxaline and 10mmol triphenylethylene borate (0.45mM, 171.9mg) in 25mL of toluene- Mixed solvent of 5mL absolute ethanol-5mL sodium carbonate aqueous solution (1mol / L), after vacuuming and changing nitrogen three times, add 1.5mmol Pd(PPh 3 ) 4 , heated the reaction system to 95°C, stirred and refluxed for 12 hours, then spotted the plate by TLC to detect the completion of the reaction of the raw materials, stopped heating and cooled to room temperature, washed the reaction solution with water for 3 times, and then washed with CH 2 Cl 2 Extracted 3 times with anhydrous NaSO 4 Dry, filter, remove the solven...

Embodiment 2

[0041] Embodiment 2: prepare pyridinium salt quinoxaline compound PQ2

[0042] (1) Preparation of 5,8-dibromo-2,3-bis(4-methoxybenzene)quinoxaline according to literature H.J.Song, D.H.Kim, E.J.Lee, J.R.Haw, D.K.Moon, Sol.Energ.Mat. Prepared by the method disclosed in Sol.C.2014, 123, 112-121.

[0043] (2) Dissolve 10mmol of 5,8-dibromo-2,3-bis(4-methoxybenzene)quinoxaline and 10mmol triphenylethylene borate (0.45mM, 171.9mg) in 25mL of toluene- Mixed solvent of 5mL absolute ethanol-5mL sodium carbonate aqueous solution (1mol / L), after vacuuming and changing nitrogen three times, add 0.8mmol Pd(PPh 3 ) 4 , heated the reaction system to 95°C, stirred and refluxed for 12 hours, then spotted the plate by TLC to detect the completion of the reaction of the raw materials, stopped heating and cooled to room temperature, washed the reaction solution with water for 3 times, and then washed with CH 2 Cl 2 Extracted 3 times with anhydrous NaSO 4 Dry, filter, remove the solvent by r...

Embodiment 3

[0046] Embodiment 3: prepare pyridinium salt quinoxaline compound PQ3

[0047] (1) Preparation of 5,8-dibromo-2,3-bisphenylquinoxaline according to literature Y.Chen, Y.Ling, L.Ding, C.Xiang and G.Zhou, J.Mater.Chem.C. 2016, 4:4 (2016) 8496-8505 disclosed method preparation.

[0048] (2) Dissolve 10mmol of 5,8-dibromo-2,3-bisphenylquinoxaline and 10mmol triphenylethylene borate (0.45mM, 171.9mg) in 25mL toluene-5mL absolute ethanol-5mL Sodium carbonate aqueous solution (1mol / L) mixed solvent, after vacuumizing and changing nitrogen three times, add 1.5mmol Pd (PPh 3 ) 4 , heat the reaction system to 60°C, stir for 5 hours, then spot the plate by TLC to detect the completion of the reaction of the raw materials, stop heating and cool to room temperature, wash the reaction solution with water for 3 times, and then wash with CH 2 Cl 2 Extracted 3 times with anhydrous NaSO 4 Dry, filter, remove the solvent by rotary evaporation, and separate by silica gel column chromatograph...

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Abstract

The invention discloses a water-soluble aggregation-induced emission quinoxaline compound, a preparation method thereof and an application of the compound. According to the method, 1, 4-dibromo-2, 3-diaminobenzene and o-diketone with an equal molar weight react to obtain 1, 4-dibromo-quinoxaline, the 1, 4-dibromo-quinoxaline is sequentially subjected to Suzuki reaction with triphenyl ethylene boric acid ester and pyridine boronic acid to obtain a quinoxaline neutral compound containing triphenylethylene and pyridine components, and the quinoxaline neutral compound further reacts with a nucleophilic reagent containing active methylene to obtain the pyridinium salt functionalized water-soluble aggregation-induced emission quinoxaline compound. The prepared water-soluble aggregation-induced emission quinoxaline compound can be dissolved in mixed solvents of water / organic solvents with the water volume percent content of 95%-60%. The compound has excellent aggregation-induced emission performance and water solubility and can be used as a fluorescent probe and a solid light-emitting material.

Description

technical field [0001] The invention belongs to the field of synthesis of fluorescent small molecule materials, and relates to a water-soluble aggregation-induced luminescent quinoxaline compound and a preparation method thereof and its application to fluorescent probes and solid luminescent materials. Background technique [0002] Since Professor Tang Benzhong first proposed the concept of Aggregation-induced emission (AIE), materials with strong solid-state luminescence have attracted much attention [(1) J.Mei, N.L.C.Leung, R.T.K.Kwok, J.W.Y.Lam, B.Z.Tang, Chem.Rev., 2015, 115, 11718-11940; (2) Z.Chi, X.B.Zhang, Xu, X.Zhou, C.Ma, Y.Zhang, S.Liu, J.Xu, Chem.Soc.Rev ., 2012, 41, 3878-3896]. Studies have shown that AIE molecules usually have a special twisted conformation, and their luminescence ability is poor in solution, but in the solid state, because the free rotation around the single bond in the molecule is inhibited, which is conducive to the occurrence of radiative ...

Claims

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Application Information

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IPC IPC(8): C07D401/04C09K11/06G01N21/64
CPCC07D401/04C09K11/06C09K2211/1044G01N21/6428
Inventor 汪凌云崔明明曹德榕
Owner SOUTH CHINA UNIV OF TECH
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