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Luminescent material with aggregation-induced luminescent properties and its preparation and application

A technology for aggregation-induced luminescence and luminescent materials, which is applied in the field of luminescent materials with aggregation-induced luminescence properties and their preparation, can solve the problems of non-renewable, expensive rare earth metals, limited resources, etc., and achieves mild reaction conditions, low cost of raw materials, The effect of high reaction yield

Active Publication Date: 2020-09-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Rare earth metals are expensive, and the resources are limited and non-renewable

Method used

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  • Luminescent material with aggregation-induced luminescent properties and its preparation and application
  • Luminescent material with aggregation-induced luminescent properties and its preparation and application
  • Luminescent material with aggregation-induced luminescent properties and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of aggregation-induced luminescent material (INDO-DH), the structural formula is:

[0050]

[0051] The synthetic route is as follows:

[0052]

[0053] 2-indolinone (1.07g, 8mmol) and benzophenone (1.75g, 9.6mmol) were dissolved in 50mLTHF, followed by adding pyridine (1.3mL, 16mmol), tetraisopropyl titanate (Ⅳ) ( 7.1mL, 24mmol), the mixture in N 2 Reflux (60°C) for 5 h under protection, spin dry THF with a vacuum rotary evaporator, and then use DCM / H 2 O was dissolved and the filtrate was extracted three times with a Buchner funnel. After the DCM layer was concentrated and purified by column chromatography, a yellow solid INDO-DH (aggregation-induced luminescent material) was obtained, with a yield of 1.99 g and a yield of 83.7%.

[0054] 1 H NMR (500MHz, CDCl 3 )δ(TMS,ppm):8.11(s,1H),7.41-7.45(m,3H),7.35-7.38(m,5H),7.30-7.33(m,2H),7.08(t,J=7.7Hz ,1H),6.72(d,J=7.6Hz1H),6.64(t,J=7.7Hz,1H),6.37(d,J=7.8Hz,1H).

[0055] 13 C NMR (126MHz, CDCl 3 )...

Embodiment 2

[0058] Preparation of aggregation-induced luminescence material (INDO-DF), the structural formula is:

[0059]

[0060] The synthetic route is as follows:

[0061]

[0062] Dissolve 2-indolinone (1.07g, 8mmol) and 4,4'-difluorobenzophenone (2.09g, 9.6mmol) in 50mLTHF, then add pyridine (1.3mL, 16mmol), tetraisotitanate Propyl ester (Ⅳ) (7.1mL, 24mmol), the mixture in N 2 Reflux the reaction for 5 h under protection, spin dry THF with a vacuum rotary evaporator, and then use DCM / H 2 O was dissolved and the filtrate was extracted three times with a Buchner funnel. After the DCM layer was concentrated and purified by column chromatography, a yellow solid INDO-DF (aggregation-induced luminescent material) was obtained with a yield of 2.44 g and a yield of 91.7%.

[0063] 1 H NMR (500MHz, CDCl 3 )δ(TMS,ppm):7.64(s,1H),7.38-7.37(m,4H),7.13(m,3H),7.04(t,J=8.7Hz,2H),6.78(d,J=7.8 Hz,1H),6.70(t,J=7.7Hz,1H),6.44(d,J=7.8Hz,1H).

[0064] 13 C NMR (126MHz, CDCl3) δ (TMS, ppm): ...

Embodiment 3

[0067] Preparation of aggregation-induced luminescent material (INDO-TOMe), the structural formula is:

[0068]

[0069] The synthetic route is as follows:

[0070]

[0071] (1) At 0°C, add thionyl chloride (2.2ml, 30mmol) into a solution of phenylpropylic acid (1.46g, 10mmol) in DCM (40mL) for reflux reaction for 5h, and spin off the solvent with a rotary evaporator A yellow oil was obtained; then it was added dropwise to a THF (40mL) solution of pyridine (2.4ml, 30mol) and o-iodoaniline (2.08g, 9.5mmol), reacted at room temperature for 3h, then stopped the reaction, concentrated and passed column chromatography Separation and purification gave white solid acetylene ketimine intermediate f (2.62g) with a yield of 79.3%;

[0072] (2) The acetylene ketimine intermediate f (1.04g, 3mmol), 3,4,5-trimethoxyphenylboronic acid (1.27g, 6mmol) and tetrakis (triphenylphosphine) palladium obtained in (1) (346.7mg, 0.3mmol), cuprous thiophene-2-carboxylate (1.14g, 6mmol) and THF ...

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Abstract

The invention belongs to the technical field of luminescent materials, and discloses a luminescent material having aggregation-induced emission property as well as preparation and application thereof.A molecular general formula of the luminescent material is as shown in a formula I which is shown in the description, wherein R1 and R2 are different or same electron donating or electron withdrawinggroups, and R3 and R4 are simultaneously hydrogen or methoxy groups. The luminescent material disclosed by the invention is stable in structure, has the aggregation-induced emission property and is good in luminescent performance, and the highest efficiency of crystalline-state fluorescent quanta can be up to 20.7 percent; meanwhile, a preparation method of the luminescent material is simple in operation, gentle in reaction conditions and high in reaction yield; the luminescent material has the advantages that solid-state luminescence can be realized, the cost of raw materials is low, regeneration is realized, regulation of light color can be easily realized through accessing different electron donating and electron withdrawing groups, and the like, and the luminescent material is beneficial for large-scale popularization, and the problem of energy depletion is solved; meanwhile, the luminescent material has mechanoluminescence property, and can be applied to the fields of fake prevention, real-time pressure change monitoring and the like. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and in particular relates to a kind of luminescent material with aggregation-induced luminescent properties, a preparation method and application thereof. Background technique [0002] Compared with inorganic materials, organic light-emitting materials have the advantages of large Stokes shift, easy adjustment of light color, bendability, convenient preparation, and renewable raw materials. Based on these advantages, organic light-emitting materials have been widely used in chemical sensing, biological imaging, fluorescent probes and optoelectronics. However, due to the large planar structure of traditional organic light-emitting materials, the molecules are tightly packed, often due to the π-π stacking effect, resulting in fluorescence quenching. However, in practical applications, light-emitting materials such as organic light-emitting diodes and nanoparticles usually exist in th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34C07D209/86C09K11/06G01N21/64
CPCC07B2200/13C07D209/34C07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/6486
Inventor 唐本忠胡蓉蓉李飞霞赵祖金秦安军
Owner SOUTH CHINA UNIV OF TECH
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