Amphiphilic illuminant with aggregation induced emission characteristics and applications thereof

An aggregation-induced luminescence and aggregation-induced technology, applied in the field of fluorescent materials, can solve the problems of limited application and achieve the effect of long cycle life

Active Publication Date: 2015-10-14
HKUST SHENZHEN RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide an amphiphilic luminescent substance with aggregation-induced luminescent properties and its application, which sol...

Method used

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  • Amphiphilic illuminant with aggregation induced emission characteristics and applications thereof
  • Amphiphilic illuminant with aggregation induced emission characteristics and applications thereof
  • Amphiphilic illuminant with aggregation induced emission characteristics and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1: Synthesis of non-ionic amphiphilic luminescent substances P1 / 6, P2 / 6 and P3 / 6 and experimental research on their application

[0082] (1) Synthesis (n, m, o and p respectively represent natural numbers from 2 to 3000)

[0083]

[0084] like figure 1 As shown, the supply ratio of the reagents used in the synthesis of luminescent substance P1 / 6 is as follows, the concentration ratio between the sixth compound 6, the first compound 1, CuBr and PMDETA [6] / [1] / [CuBr] / [PMDETA] is 1 / 4 / 4 / 4, the supply ratio of the reagents for synthesizing luminescent substances P2 / 6 and P3 / 6 is different from that of luminescent substance P1 / 6 in that the sixth compound 6 is different from the second compound 2 and the second compound 6 respectively. The concentration ratio of the three compounds 3 is [6] / [2] / [3]=1 / 1 / 0.5. At room temperature, the sixth compound 6 (1.05 mg, 0.3 mmol) and the first compound 1 (430 mg, 1.2 mmol) was carried out chain reaction, after stirring for ...

Embodiment 2

[0095] Example 2: Synthesis of cationic amphiphilic luminescent material TPE-MEM and experimental research on its application

[0096] (1) synthesis

[0097]

[0098] like figure 2 As shown, under nitrogen atmosphere, 1-(3-trimethylaminopropyl)-4-methylpyridine dibromide (1-(3-trimethylammoniopropyl)-4-methylpyridinium dibromide) (0.5g, 1.4mmol ) and the solution of the third compound 3 (1.5016g, 2.8mmol) were refluxed in absolute ethanol, and three drops of piperidine were added for catalysis. After cooling to room temperature, the solvent was evaporated under reduced pressure and passed through silica gel column chromatography. The residue was purified using a mixed solvent of dichloromethane and methanol (2:1 v / v) as eluent to give a yellow product TPE-MEM (0.72 g, 59%). 1 H NMR (400MHz, methanol-d 4 ,δ):8.948(d,2H,J=6.8Hz),8.213-8.190(m,2H),7.946(6,1H,J=16Hz),7.737-7.717(m,2H),7.576(d,2H ,J=8Hz),7.430-7.331(m,3H),7.061-6.843(m,14H),6.605-6.570(m,2H),4.698(t,2H,J=15...

Embodiment 3

[0113] Example 3: Synthesis of anionic amphiphilic luminescent material TPE-2Gd and experimental research on its application

[0114] (1) Synthesis of TPE-2+

[0115]

[0116] like image 3As shown, under nitrogen atmosphere, 1-(3-trimethylaminopropyl)-4-methylpyridine dibromide (1-(3-trimethylammoniopropyl)-4-methylpyridinium dibromide) (0.5g, 1.4mmol ) and 4-(1,2,2-triphenylvinyl)benzaldehyde (4-(1,2,2-triphenylvinyl)benzaldehyde) (1.01g, 2.8mmol) were refluxed in anhydrous methanol, Three drops of piperidine were added for catalysis, and after cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, using a mixed solvent of dichloromethane and methanol (2:1 v / v) as the eluent. The agent was removed to obtain the yellow product TPE-2+ (0.56g, 57%). 1 H NMR (400MHz, methanol-d 4 ,δ):8.913(d,2H,J=6.8Hz),8.177(d,2H,J=6.8Hz),7.875(d,1H,J=16.0Hz),7.501(d,2H,J=8.4Hz ),7.352(d,1H,J=16.4...

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Abstract

The invention relates to an amphiphilic illuminant with aggregation induced emission characteristics and applications thereof. The illuminant is prepared by connecting a hydrophilia unit on a classical hydrophobicity unit of the classical aggregation induced emission characteristics (AIE), and can be applied to a fluorescent light chemical sensor and is used for preparing fluorescent light coloring agent which is used for coloring living cells and animal imaging fluorescent light. The amphiphilic coloring agent is specifically suitable for the fluorescent light mark on biopolymer, and can be used as a biocompatibility probe for AIE activation so that the amphiphilic coloring agent can be applied to clinic cancer imaging, diagnose and treatment.

Description

technical field [0001] The invention relates to the technical field of fluorescent materials, in particular to an amphiphilic luminescent substance with aggregation-induced luminescent properties and an application thereof. Background technique [0002] In recent years, it has been found that a series of helical molecules do not emit light in solution, but are induced to emit strong light after polymerization. The aggregation fluorescence quenching effect is exactly the opposite. Using this new effect, AIE luminescent materials can be applied in many high-tech fields, such as chemical sensors, biological probes, immunolabeling, stimuli-responsive materials and solid-state emitters, etc. [Chem.Commun.2001,18,1740; J.Mater. Chem.,2001,11,2974; Chem.Soc.Rev.,2011,40,5361; Adv.Funct.Mater.,2012,22,771; Chem.Commun.,2011,47,7323; Adv.Healthcare Mater., 2013,2,500; Acc.Chem.Res., 2013,46,2441; Chem.Commun.2013,49,11335; Biomaterials 2008,29,1345; US 8,029,767; US 2013 / 0029325; C...

Claims

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Application Information

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IPC IPC(8): C09K11/06C08G65/00C08G65/48A61K41/00A61K49/00A61K49/10A61K31/4425A61K31/555A61P35/00
CPCA61K31/4425A61K31/555A61K41/00A61K41/0057A61K49/00A61K49/10C07D213/38C07D249/06C08G65/00C08G65/333C08G65/48C09K11/06C09K2211/1029C09K2211/1466C09K2211/182G01N1/30
Inventor 唐本忠陈奕龙林荣业
Owner HKUST SHENZHEN RES INST
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