Double-phase organic fluorescent materials with relatively strong fluorescence in solid state and liquid state and preparation method thereof

A fluorescent material, solid-state technology, applied in the fields of luminescent materials, fluorescence/phosphorescence, semiconductor/solid-state device manufacturing, etc., can solve the problems of fluorescence quenching, excited state energy dissipation, limitation, etc., achieves simple operation, simple preparation method, The effect of high fluorescence quantum efficiency

Inactive Publication Date: 2018-03-06
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional fluorescent materials will have strong fluorescence in a dilute solution state, but in a concentrated solution or solid film state, due to the π-π interaction between molecules, they form a close stack, resulting in most of the excited state energy being in the form of non-radiative In the form of dissipation, fluorescence quenching (ACQ) occurs; in the practical application of fluorescent materials, they often need to be processed into the desired shape, that is, they are used in solid state or thin film state, so the fluorescence of these materials is quenched, which limits The application of traditional fluorescent materials in film formation or solid state

Method used

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  • Double-phase organic fluorescent materials with relatively strong fluorescence in solid state and liquid state and preparation method thereof
  • Double-phase organic fluorescent materials with relatively strong fluorescence in solid state and liquid state and preparation method thereof
  • Double-phase organic fluorescent materials with relatively strong fluorescence in solid state and liquid state and preparation method thereof

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preparation example Construction

[0036] The preparation of compound 3: similar to the synthesis of compound 1, under an inert atmosphere, make compound b in Pd(PPh 3 ) 4 In the presence of a catalyst, react with p-esteryl phenylboronic acid to obtain compound 3.

[0037] The fluorescent material synthesized by the invention has strong fluorescent emission in both solid state and solution state, and both the solid state and liquid state fluorescent quantum yields are relatively high. The fluorescent material has different visible fluorescent responses in solvents of different polarities, and has good solvent effect. The preparation method of the fluorescent material is simple, the operation is convenient, and it has potential application prospects in the fields of organic photoelectric materials, biochemical detection, solid-liquid two-phase luminescence and the like.

Embodiment 1

[0039] Embodiment 1: the synthesis of compound b

[0040] The synthesis is divided into two steps:

[0041] (1) The first step is the coupling reaction of p-bromophenylacetylene:

[0042] In a 100mL three-necked flask with an air duct, add 1.50mmol of CuCl, 1.02mmol of N,N,N',N'-tetramethylethylenediamine (TMEDA) and 110mL of toluene respectively, and air 0.5mL at room temperature h, after stirring evenly, add 27.62 mmol of p-bromophenylacetylene, heat up to 45°C and react for 10 hours, then stop. Then remove toluene, dissolve with appropriate amount of dichloromethane, wash with 5% hydrochloric acid solution and water, remove the solvent after drying the organic phase, and recrystallize the obtained crude product with tetrahydrofuran and n-hexane to obtain 1,4-di-p-bromophenyl 4.2 g of pale yellow needle-like crystals of diacetylene, yield 84%.

[0043] (2) The second step is the synthesis of compound b:

[0044] Add 5.6mmol of 1,4-di-p-bromophenylbutadiyne, 2.8mmol of anil...

Embodiment 2

[0045] Embodiment 2: the synthesis of compound 1

[0046] Add 1.1 mmol of compound b, 2.8 mmol of p-formylphenylboronic acid, 0.06 mmol of tetrakis(triphenylphosphine)palladium and 6.3 mmol of sodium carbonate into a single-port reaction flask, and raise the temperature to 80°C for 12 hours under an inert gas atmosphere. , the resulting crude product was separated by column chromatography using pure dichloromethane as the eluent, and then recrystallized from tetrahydrofuran and n-hexane to obtain 0.31 g of a yellow powder with a yield of 55%; its nuclear magnetic spectrum is shown in the attached figure 1 .

[0047] 1 H NMR (400MHz, DMSO), (δ, TMS, ppm) 10.04(s, 2H), 7.96(d, J=8.3 Hz, 4H), 7.89(d, J=8.2Hz, 4H), 7.64(d, J=8.4Hz, 4H), 7.42(s, 3H), 7.21(t, J=11.0Hz, 6H), 6.65(s, 2H).

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Abstract

The invention provides double-phase organic fluorescent materials with relatively strong fluorescence in the solid state and the solution state and a preparation method and application thereof. Particularly, the invention provides arylpyrrole derivative fluorescent materials shown as a general formula (TPP-R) and having relatively strong solid-state and solution-state two-phase fluorescence emission: FORMULA, wherein R is an electron-withdrawing group, an aldehyde group, cyano or an ester group. The invention further provides a preparation method of the aryl-substituted pyrrole derivative fluorescent materials. The prepared fluorescent materials have relatively high fluorescence quantum efficiency and significant solvent effect in the solid state and the liquid state, and the medium-polarity electron-withdrawing enables one of the fluorescent materials to have light-emitting characteristics in different aggregation morphologies. The fluorescent materials with relatively strong light-emitting characteristics in the solid state and the solution state have a good application prospect in organic light-emitting diodes, chemical detection, biological detection and other aspects.

Description

technical field [0001] The invention relates to a class of organic fluorescent materials and a preparation method thereof, in particular to a class of special fluorescent materials with strong fluorescence in both solid and solution states and good solvent effect and a preparation method thereof. Background technique [0002] Organic light-emitting materials have received extensive attention due to their huge applications in many fields such as light-emitting diodes (LEDs), specific molecular recognition and tracking, photochemical sensors, and bioimaging. Traditional fluorescent materials will have strong fluorescence in a dilute solution state, but in a concentrated solution or solid film state, due to the π-π interaction between molecules, they form a close stack, resulting in most of the excited state energy being in the form of non-radiative In the form of dissipation, fluorescence quenching (ACQ) occurs; in the practical application of fluorescent materials, they often...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/333C07D207/337C09K11/06H01L51/42H01L51/46G01N21/64
CPCG01N21/6428C09K11/06C07D207/333C07D207/337C09K2211/1007C09K2211/1029H10K85/654H10K30/00Y02E10/549
Inventor 支俊格李园园雷云祥董立超董宇平石建兵佟斌
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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