Organic room-temperature phosphorescent polymer, preparation thereof and application of organic room-temperature phosphorescent polymer in X-ray imaging

A room temperature phosphorescence, polymer technology, applied in luminescent materials, chemical instruments and methods, etc., can solve the problems of strict growth conditions, difficult reproducibility, application limitations, etc. Effect

Active Publication Date: 2022-05-27
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The existing long-life room temperature phosphorescent materials are mainly obtained by crystallization induction, which means that strict growth conditions and difficult repeatability are unavoidable, and the room temperature phosphorescent materials prepared by this method have no room temperature phosphorescence in the amorphous state, which in turn Further limit the scope of application of this type of material
[0004] Chinese patent CN 112210037 A discloses an organic phosphonium salt-type long-life room temperature phosphorescent polymer material, which uses triphenylphosphine as a raw material to obtain organic phosphonium salt monomers with different alkenyl chain lengths through phosphating reaction; Copolymerized with acrylamide to obtain high-efficiency and long-lived room-temperature phosphorescent polymer, which realizes the long-life room-temperature phosphorescence of the material in the amorphous state; the material obtained by this scheme has good solubility in water, so it can be used to make safe Ink is used in the field of security printing, but its solubility in organic solvents is not good, its application is still relatively limited, and this type of material does not show radioluminescent properties, so it is difficult to prepare non-toxic inks with good performance based on this material. Crystalline Organic Scintillator Materials

Method used

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  • Organic room-temperature phosphorescent polymer, preparation thereof and application of organic room-temperature phosphorescent polymer in X-ray imaging
  • Organic room-temperature phosphorescent polymer, preparation thereof and application of organic room-temperature phosphorescent polymer in X-ray imaging
  • Organic room-temperature phosphorescent polymer, preparation thereof and application of organic room-temperature phosphorescent polymer in X-ray imaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of PTPA

[0036] The chemical structural formula of PTPA is as follows:

[0037]

[0038] The synthesis of PTPA is divided into three steps:

[0039] 1) Under a nitrogen atmosphere, dissolve 4-bromotriphenylamine (1.0equiv) in an ultra-dry tetrahydrofuran solution, add n-butyllithium (1.2equiv) at -78°C to react for 1 h, and then add diphenylphosphorus chloride ( 1.0equiv) reacted for 12h, spin-dried under reduced pressure, and purified by column chromatography to obtain MT;

[0040] 2) Under a nitrogen atmosphere, dissolve MT (1.0 equiv) in DMF, add 4-bromo-1-butene (2.0 equiv), heat at 120° C. for 18 h, distill under reduced pressure, spin dry, and purify by column chromatography to obtain MTPA;

[0041] Characterization of compound MTPA: 1 H NMR (400MHz, DMSO-d 6 ): δ7.78(s,11H),7.29(s,12H),7.04–6.84(m,2H),5.96–5.74(m,1H),5.39–4.93(m,2H),3.70–3.47(m ,2H),2.38–2.05(m,2H). 13 CNMR (100MHz, DMSO-d 6 ,δ): 162.66, 153.25, 145.09, 135.43, ...

Embodiment 2

[0045] Embodiment 2: the preparation method of PCBA

[0046] The chemical structural formula of PCBA is as follows:

[0047]

[0048] The synthesis of PCBA is divided into three steps:

[0049] 1) Under nitrogen atmosphere, dissolve 3-bromo-9-butanecarbazole (1.0equiv) in ultra-dry tetrahydrofuran solution, add n-butyllithium (1.2equiv) at -78°C to react for 1h, add diphenyl chloride Phosphorus (1.0equiv) was reacted for 12h, spin-dried under reduced pressure, and purified by column chromatography to obtain MC;

[0050] 2) Under nitrogen atmosphere, dissolve MC (1.0 equiv) in DMF, add 4-bromo-1-butene (2.0 equiv), heat at 120° C. for 18 h, spin dry under reduced pressure, and purify by column chromatography to obtain MCBA;

[0051] Characterization of compound MCBA: 1 H NMR (400MHz, DMSO-d6): δ8.89–8.75 (m, 1H), 8.33–8.23 (m, 1H), 7.99–7.68 (m, 14H), 7.38–7.28 (m, 1H), 6.06– 5.80(m,1H), 5.26–5.00(m,2H), 4.51(s,2H), 3.86–3.67(m,2H), 2.41–2.25(m,2H), 1.88–1.68(m,2H), 1....

Embodiment 3

[0055] Example 3: Preparation method of PBNA

[0056] The chemical structural formula of PBNA is as follows:

[0057]

[0058] The synthesis of PCBA is divided into three steps:

[0059] 1) Under a nitrogen atmosphere, dissolve 2,6-dibromonaphthalene (1.0 equiv) in an ultra-dry tetrahydrofuran solution, add n-butyllithium (1.2 equiv) at -78°C to react for 1 h, add diphenylphosphorus chloride ( 1.0equiv) reacted for 12h, spin-dried under reduced pressure, and purified by column chromatography to obtain MB;

[0060] 2) Under nitrogen atmosphere, dissolve MB (1.0 equiv) in DMF, add 4-bromo-1-butene (2.0 equiv), heat at 120° C. for 18 h, spin-dry under reduced pressure, and purify by column chromatography to obtain MBNA ;

[0061] Characterization of compound MBNA: 1 H NMR (400MHz, DMSO-d 6 ): δ8.67–8.54(m,1H),8.53–8.39(m,1H),8.32–8.24(m,1H),8.16–8.11(m,1H),7.94–7.76(m,13H),6.04 –5.80(m,1H),5.27–5.03(m,2H),3.90–3.69(m,2H),2.42–2.22(m,2H). 13 C NMR (100MHz, DMSO-d 6 ,δ):...

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Abstract

The invention discloses an organic room-temperature phosphorescent polymer and preparation and application thereof in X-ray imaging, the organic room-temperature phosphorescent polymer material is obtained by reacting different brominated groups with diphenyl phosphorus chloride, grafting an olefin chain and then copolymerizing with acrylic acid, and the organic room-temperature phosphorescent polymer material comprises PTPA, PTPA-Br, PTPA-2Br, PCBA, PCBA-Br, PCBA-2Br, PBNA, PPAE and PPYE. The organic room temperature phosphorescent polymer material shows a strong radiation luminescence (RL) characteristic under R-ray irradiation; besides, the polymer can be dissolved in an organic solvent, so that the polymer can be made into a scintillator to be successfully applied to the field of X-ray imaging, and a promising way is provided for expanding the application range of the amorphous organic scintillator.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric functional materials, in particular to a class of organic room temperature phosphorescent polymers and their preparation and application in X-ray imaging. Background technique [0002] X-ray excited luminescent material, namely scintillator, is a new type of material that can convert high-energy x-ray photons into low-energy visible light emitting, and is widely used in radiation detection, biomedicine, security inspection and other fields. However, such X-ray excited luminescent materials are mainly limited to inorganic materials or heavy metal complexes. Inorganic materials with such properties have inherent disadvantages such as harsh preparation conditions, high cost of rare metal resources, and high toxicity for biological applications. subject to many restrictions. In recent years, pure organic materials have become a powerful alternative to traditional inorganic scintillator ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F230/02C08F220/06C09K11/06
CPCC08F230/02C08F220/06C09K11/06C09K2211/1433C09K2211/1425C09K2211/1416C09K2211/1466Y02E10/549
Inventor 马云魏娟刘晨园赵强刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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