An activated luminescence material and a method for preparing the same

A technology of light-emitting materials and groups, applied in the field of fluorescent materials

Active Publication Date: 2015-06-03
HKUST SHENZHEN RES INST +1
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide an activated luminescent material and its preparation method, to solve the urgent need of biocompatible AIE activated luminescent material for cell imaging and for the detection of explosives in the prior art

Method used

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  • An activated luminescence material and a method for preparing the same
  • An activated luminescence material and a method for preparing the same
  • An activated luminescence material and a method for preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] (1) The structural formula of TPE-β-CD

[0068]

[0069] (2) Preparation of TPE-β-CD inclusion compound activated luminescent material

[0070] In a nitrogen atmosphere, 0.188g (0.5mmol) TPE-CO 2 H and 0.5675g (0.5mmol) β-CD were dissolved in 10ml of anhydrous dimethylformamide (DMF), and after dissolving, 0.103g (0.5mmol) of N,N-dicyclohexylcarbodiimide ( dicyclohexylcarbodiimide, DCC) in 5ml of anhydrous DMF; in a nitrogen environment, stirred at room temperature for 3 days; filtered, the filtrate was added dropwise to a large amount of diethyl ether under vigorous stirring, and a solid was precipitated; then The solid was separated by filtration again, and the solid was dried under vacuum at 40° C. overnight, with a yield of 70%. 1 H NMR (400MHz, DMSO-d 6 ), δ(TMS,ppm):3.28(d,7H,H 4 ),3.33(d,7H,H 2 ),3.55(d,7H,H 5 ),3.60(d,12H,H 6 ),3.64(br,7H,H 3 ),4.44(t,6H,O 6 H),4.80(d,7H,H 1 ),5.65(s,7H,O 3 H),5.70(d,7H,O 2 H), 7.93(s,2H,Ar-H).13 C NMR (400MHz, DM...

Embodiment 2

[0072] (1) The structural formula of TPE-α-CD:

[0073]

[0074] (2) Preparation of TPE-α-CD inclusion compound activated luminescent material

[0075] In a nitrogen atmosphere, at 0°C, 0.188g (0.5mmol) of TPE-CO 2 H and 0.486g (0.5mmol) α-CD were dissolved in 15ml of anhydrous dimethylformamide (DMF), and 0.103g (0.5mmol) of DCC was added as a catalyst; in a nitrogen environment, warm to room temperature and stir React for 3 days; filter, add the filtrate dropwise to a large amount of diethyl ether under the condition of vigorous stirring, and precipitate the solid; then filter again to obtain the solid, dry the solid overnight at 40°C under vacuum, and the yield 60%. 1 H NMR (400MHz, DMSO-d 6 ), δ(TMS,ppm):3.30(m,6H,H 4 ),3.36(m,6H,H 2 ),3.56(d,6H,H 5 ),3.61(m,10H,H 6 ),3.75(t,6H,H 3 ),4.46(t,5H,O 6 H),4.77(d,6H,H 1 ),5.41(d,6H,O 3 H),5.50(d,6H,O 2 H), 7.93(s,2H,Ar-H). 13 C NMR (400MHz, DMSO-d 6 ), δ(TMS,ppm): 59.7(C 6 ),71.8(C 2 ),72.3(C 5 ),72.9(C 3 ),...

Embodiment 3

[0077] (The structural formula of 1TPE-γ-CD:

[0078]

[0079] (2) Preparation of TPE-γ-CD inclusion compound activated luminescent material

[0080] In a nitrogen atmosphere, at 0°C, 0.188g (0.5mmol) of TPE-CO 2 H, 0.648g (0.5mmol) γ-CD and 0.103g (0.5mmol) DCC were dissolved in 15ml of anhydrous dimethylformamide (DMF); in a nitrogen environment, stirred and reacted at room temperature for 3 days; Filtrate, add the filtrate dropwise to a large amount of diethyl ether under vigorous stirring, and precipitate a solid; then filter again to separate the solid, and dry the solid overnight at 40°C under vacuum, with a yield of 52%. 1 H NMR (400MHz, DMSO-d 6 ), δ(TMS,ppm):3.28(d,8H,H 4 ),3.33(d,8H,H 2 ),3.55(d,8H,H 5 ),3.60(d,16H,H 6 ),3.64(br,8H,H 3 ),4.44(t,7H,O 6 H),4.80(d,8H,H 1 ),5.65(s,8H,O 3 H),5.70(d,8H,O 2 H),6.9-7.1(m,4H,Ar-H),7.93(s,2H,Ar-H). 13 C NMR (400MHz, DMSO-d 6 ):δ(TMS,ppm):59.7(C 6 ),71.8(C 2 ),72.3(C 5 ),72.9(C 3 ), 81.3 (C 4 ), 101.7(C 1 ...

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Abstract

The invention relates to the technical field of fluorescent material, specifically to an activated luminescence material and a method for preparing the same. Different biomolecules are combined to tetraphenyl ethylene through condensation reaction, so the biocompatible activated luminescence material having AIE/AEE features can be obtained. The biomolecules contain water soluble activated luminescence molecules with high fluorescent quantum yield, which have excellent biocompatibility in a solution state and a solid state, and crystalline polymer which can form nanosheets in a water-soluble medium. The obtained activated luminescence material can be applied to living cell fluorescence staining, sensitive explosive detecting and the like.

Description

technical field [0001] The invention relates to the technical field of fluorescent materials, in particular to an activated luminescent material and a preparation method thereof. Background technique [0002] Organic luminescent materials have attracted more and more attention because of their wide range of applications. Currently, organic luminescent materials are mainly used in bioimaging (Chem.Sci., 2012, 3, 984), electronic technology (Adv. .Sci.,2011,2,2402; Chem.Rev.2007,107,1011), optical technology (Adv.Master.,2012,24,1703-1708) and storage media (Adv.Master.,2012,24, 1255-1261) and other fields, but due to the phenomenon of aggregation-caused quenching (ACQ) caused by energy transfer and the formation of excimers and exciplexes, the traditional planar dyes The luminescence is weak in the solid state, which will seriously limit the application of planar dyes in the engineering industry. [0003] In 2001, some inventors discovered a new type of activated luminescen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C08B37/16C08G63/91G01N33/52G01N21/64
Inventor 唐本忠梁国栋秦玮林荣业
Owner HKUST SHENZHEN RES INST
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