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Surfactant with aggregation-induced emission effect

A technology of aggregation-induced luminescence and surfactants, which is applied in the direction of luminescent materials, preparation of organic compounds, organic chemistry, etc., can solve the problems of poor contrast, difficulty in observing and distinguishing aggregates, and achieve simple preparation, Good stability and enhanced fluorescence effect

Inactive Publication Date: 2016-10-12
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the electron microscope sample is a solid, the observed image is not necessarily the true state of the surfactant in the solution state
In addition, the composition of surfactant molecules is mostly carbon, hydrogen, and oxygen, resulting in poor contrast under the electron microscope and difficult to be distinguished
Another feasible visualization technique is to use fluorescence microscopy, but because the luminophores of existing fluorescent surfactants all have aggregation-induced quenching effects, it is difficult to observe aggregates after surfactant aggregation

Method used

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  • Surfactant with aggregation-induced emission effect
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  • Surfactant with aggregation-induced emission effect

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Synthesis of TPE-DTAB

[0031] A. Under nitrogen protection, add 0.182g (0.50mmol) of 4,4'-(1,2-distyryl-1,2-substituted)benzenediol and 10mL of anhydrous N,N-Dimethylformamide, after stirring evenly, add 0.022g (0.55mmol) of sodium hydride, stir and react at room temperature for half an hour. Then add 0.145g (0.75mmol) of bromooctane, heat to 60°C and react for 10 hours. After the reaction is completed, N,N-dimethylformamide is distilled off under reduced pressure, and the obtained solid is obtained by water / dichloromethane system Extraction, after separating the organic phase, dry it with anhydrous sodium sulfate for 10 minutes, and distill off methylene chloride under reduced pressure again to obtain the crude product, then use petroleum ether / ethyl acetate=7:1 (v / v) as the eluent for silica gel column Purification by chromatography gave a yellow oily intermediate with a yield of 51%. 1 H NMR (600MHz, CDCl 3 ,δ):6.98-7.11(m,10H),6.83-6.92(m,4H),6.52-...

Embodiment 2

[0034] Embodiment 2: the optical property of TPE-DTAB

[0035] Dissolve 13mg of TPE-DTAB in 50mL of deionized water to prepare a 0.40mmol / L TPE-DTAB stock solution, then dilute to a concentration of 40μmol / L, and measure its ultraviolet absorption spectrum; then excite it with a wavelength of 325nm to obtain TPE - Fluorescence emission spectrum graph of DTAB, as image 3 shown. from image 3 It can be seen from the figure that the synthesized TPE-DTAB has two absorption peaks at 251nm and 320nm, corresponding to the π–π* transitions of benzene and TPE respectively, and has a strong fluorescence emission peak around 490nm after being excited. ,from image 3 The inset in can be seen that the emission of TPE-DTAB is blue-green.

Embodiment 3

[0036] Embodiment 3: the critical micelle concentration of TPE-DTAB

[0037] A. Dilute the TPE-DTAB stock solution of 0.40mmol / L successively to a concentration of 5, 10, 15, 20, 25, 30, 40, 50, 60, 70 μmol / L, excite with a wavelength of 325nm, measure its emission spectrum and Make a graph of the fluorescence intensity value corresponding to the concentration at the wavelength of 490nm, such as Figure 4 shown. from Figure 4 It can be seen from the figure that the fluorescence intensity of the synthesized TPE-DTAB aqueous solution increases with the increase of the concentration, and an inflection point appears when the concentration is 32 μmol / L, and then the increase rate of the fluorescence intensity slows down.

[0038] B. The solution prepared in above-mentioned steps A is carried out conductivity measurement, and conductivity is made curve graph to concentration, as Figure 5 shown. from Figure 5 It can be seen from the figure that the conductivity of the synthes...

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Abstract

The invention relates to surfactant with the aggregation-induced emission effect, and belongs to the technical field of surfactantluminescent materials. The structure of the surfactant with the aggregation-induced emission effect is shown as the formula (I). A preparing method is as follows, and obtained molecules have surfactant characteristics and fluorescence characteristics. Particularly, when the surfactant is in an aggregation state (micelle), fluorescence is enhanced obviously, and meanwhile the surfactant is easy to prepare and high in stability.

Description

technical field [0001] The invention belongs to the technical field of surfactant light-emitting materials, and in particular relates to a tetraphenylethylene-based surfactant with aggregation-induced light-emitting performance, preparation and performance research. Background technique [0002] Surfactant molecules are typical amphiphilic molecules, which can spontaneously form different ordered aggregation structures (such as micelles, vesicles, etc.) through intermolecular interactions. It has a wide range of applications in many disciplines. The formation mechanism and interconversion of surfactant aggregate structures are the basis for their practical application. So far, although many instrumental techniques (such as small-angle X-ray diffraction) have been used to study the formation and interconversion of various aggregates, most of them infer the relationship between different surfactant aggregates through data point collection and simulation. transition between. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/18C09K11/06C09K11/02C01B33/44C07C213/02C07C217/18C09K23/18
CPCC09K11/025C09K11/06C01B33/44C07C41/16C07C213/02C01P2002/84C01P2002/72C09K2211/1007C09K23/00
Inventor 吕超管伟江周文娟王思
Owner BEIJING UNIV OF CHEM TECH