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1,2,5-triphenyl substituted pyrrole derivative with gathering induced luminescence performance as well as preparation method and application thereof

A technology of aggregation-induced luminescence and triphenylpyridine, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effects of reducing pollution, simple preparation method, and high luminous efficiency

Inactive Publication Date: 2011-10-19
董宇平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, there is no report on aggregation-induced luminescent compounds with triaromatic substituted pyrrole as the building block in the prior art literature.

Method used

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  • 1,2,5-triphenyl substituted pyrrole derivative with gathering induced luminescence performance as well as preparation method and application thereof
  • 1,2,5-triphenyl substituted pyrrole derivative with gathering induced luminescence performance as well as preparation method and application thereof
  • 1,2,5-triphenyl substituted pyrrole derivative with gathering induced luminescence performance as well as preparation method and application thereof

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preparation example Construction

[0047] Preparation of Compound 3: Compound 3 was obtained after acidifying Compound 4 with excess hydrochloric acid.

[0048] The triphenylpyrrole derivatives with aggregation-induced luminescent properties of the present invention can also be prepared by the following synthetic route 2:

[0049] Synthetic route 2:

[0050]

[0051] Wherein the synthesis of compound b is as follows: by triphenylphosphorous palladium dichloride (Pd(PPh 3 ) 2 C1 2 ), triphenylphosphine (PPh 3 ) and cuprous iodide (CuI) in the presence of a catalytic system composed of, in an inert atmosphere, using triethylamine as a solvent and an acid-binding agent, the coupling reaction between methyl p-bromobenzoate and acetylenic alcohol is carried out to prepare the compound b.

[0052] In the preparation reaction of compound b, the catalyst triphenylphosphine palladium dichloride (Pd(PPh 3 ) 2 C1 2 ) to the reactant methyl p-bromobenzoate is preferably 0.001-0.03: 1, more preferably 0.0015-0.01...

Embodiment 1

[0062] Embodiment 1: the synthesis of compound 2

[0063] The synthesis is divided into two steps:

[0064] The first step is the coupling reaction of phenylacetylene: in a 100mL three-necked flask with an airway, add 0.05g (0.5mmol) CuCl, 0.1mL (0.6mmol) N, N, N', N'-tetramethyl ethylenediamine (TMEDA) and 60mL acetone, air was introduced at room temperature for half an hour, after stirring evenly, 4.00g (39.1mmol) phenylacetylene was added, the temperature was raised to 45°C for 8 hours, and the reaction was stopped. Use a rotary evaporator to remove the acetone solvent from the reaction solution, add an appropriate amount of dichloromethane to dissolve it, pour it into a separatory funnel, wash it with 5% hydrochloric acid solution and water in turn, take out the organic phase and use dry anhydrous magnesium sulfate powder to remove water, then evaporate The solvent was dried, and the obtained crude product was recrystallized from ethanol to finally obtain 3.214 g of white...

Embodiment 2

[0066] Embodiment 2: the synthesis of compound 4

[0067] Add 0.2 g of compound 2 (0.57 mmol) into a 100 ml single-necked bottle, add a small amount of tetrahydrofuran to dissolve, then add an appropriate amount of aqueous sodium hydroxide solution, and reflux at 70°C. After 10 hours, the hydrolysis was complete, and the reaction liquid in the bottle was dropped dropwise into excess HCL aqueous solution, and 0.14 g of the precipitate was collected, which was compound 3 with a yield of 72.5%. figure 2 .

[0068] compound 3 into 10 -3 mol / L methanol solution, and then prepare an equal volume of 10 -3 The mol / L sodium hydroxide methanol solution was mixed with the methanol solution of the above-mentioned compound 3, and stirred for 8 hours to completely neutralize the acid and alkali to obtain the compound 4 with carboxylate anions.

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Abstract

The invention provides a 1,2,5-triphenyl substituted pyrrole derivative with a gathering induced luminescence performance as well as a preparation method and an application thereof. Particularly, the invention provides a triphenyl pyrrole derivative with the gathering induced luminescence performance, which is represented by a general formula (I), wherein in the general formula (I), R1 represents H, an ester group or a carboxylate radical group; R2 represents H or a carboxylate radical group; and the premise is that R1 and R2 are not H at the same time. The invention also provides a preparation method of the triphenyl pyrrole derivative. The triphenyl pyrrole derivative with the gathering induced luminescence performance, provided by the invention, has very good application prospects in the aspects like organic light-emitting diodes, chemical detection, bioassay and the like.

Description

technical field [0001] The present invention relates to a compound with aggregation-induced luminescence properties, in particular to a triphenyl-substituted pyrrole derivative with aggregation-induced luminescence properties, its preparation method and use. Background technique [0002] Organic light-emitting compounds have been a research hotspot for researchers for half a century because of their huge applications in many fields such as light-emitting diodes (LEDs), specific molecular recognition and tracking, and photochemical sensors. In practical applications, organic light-emitting compounds will inevitably be film-formed, assembled, and even processed in the form of various aggregation states. The strong intermolecular interaction during aggregation will trigger the non-radiative deactivation process of molecules, which will lead to the weakening or even complete quenching of the fluorescence of most organic light-emitting compounds, that is, the aggregation quenchin...

Claims

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Application Information

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IPC IPC(8): C07D207/337C07D207/327C09K11/06H01L51/50H01L51/54G01N21/64
Inventor 董宇平韩天宇佟斌
Owner 董宇平
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