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Fluorescent probe with aggregation-induced emission property, and preparation method and application thereof

A technology of surfactant and alkyl, which is applied in the field of surfactant detection, can solve the problems of fluorescence self-quenching, lower detection signal-to-noise ratio, etc., and achieve the effect of low toxicity

Active Publication Date: 2017-08-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorescent materials with aggregation-induced fluorescence quenching (ACQ) properties are prone to self-quenching of fluorescence in the aggregated state, and their high background fluorescence in the solution state will significantly reduce the signal-to-noise ratio during the detection process.

Method used

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  • Fluorescent probe with aggregation-induced emission property, and preparation method and application thereof
  • Fluorescent probe with aggregation-induced emission property, and preparation method and application thereof
  • Fluorescent probe with aggregation-induced emission property, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] According to the following synthetic route, the following compounds are specifically synthesized:

[0066]

[0067] (1) Synthesis of N-(3-formyl-4-hydroxybenzyl)-N,N-dimethyloctadecyl-1-ammonium chloride (compound 3)

[0068] A mixture of 5-(chloromethyl)-2-hydroxysalicylaldehyde (340 mg, 2 mmol) and N,N-dimethyloctadec-1-amine (594 mg, 2 mmol) was stirred under reflux for 5 hours. After the reaction was complete, the precipitate was filtered and washed with diethyl ether (10 mL×2), and dried under vacuum to give the white solid product Compound 3 with a yield of 90% (841 mg).

[0069] 1 H NMR (CDCl 3 ,500MHz):δ11.26(br s,1H),8.16(d,J=3.5Hz,1H),7.80(d,J=8.5Hz,1H),7.09(d,J=8.5Hz,1H), 5.21(d, J=8.5Hz, 2H), 3.47(t, J=8.5Hz, 2H), 3.27(s, 6H), 1.26–1.25(m, 32H), 0.88(t, J=7.0Hz, 3H ); 13 C NMR(d 6 -DMSO,125MHz):190.0,162.3,140.1,132.9,122.5,118.8,118.0,65.3,63.1,48.7,31.3,29.0,29.0,28.9,28.76,28.66,28.5,25.8,22.1,21.7,13.9; ESI):m / z[M-Cl] + The computed value is C...

Embodiment 2

[0075] Embodiment 2: the detection of anionic surfactant

[0076] 15 μL of the HBT-C prepared in Example 1 18 The DMSO (1.0mM) mother solution was added to 2.985mL pure water containing different contents of anionic surfactant sodium dodecylbenzenesulfonate (SDBS), vortexed for 10s, and the fluorescence was measured with a fluorescence spectrometer (excitation wavelength 334nm).

[0077] image 3 (A) is HBT-C with the increase of SDBS concentration 18 (5μM) in H 2 Fluorescence emission spectrum in O / DMSO (99:1, v / v) solution; (B) is HBT-C with the increase of SDBS concentration 18 Fluorescence emission intensity changes at 510nm and 450nm; (C) is as the increase of SDBS concentration, HBT-C 18 The ratio of the fluorescence emission intensity at 510nm and 450nm (I 510 / I 450 )Variety. lambda ex =334nm.

[0078] Figure 4 for HBT-C 18 (5μM) in H 2 Fluorescence quantum yield as a function of SDBS concentration in O / DMSO (99:1, v / v). As can be seen from the figure, HB...

Embodiment 3

[0085] Detection of different surfactants and ions

[0086] 15 μL of the HBT-C prepared in Example 1 18 Add 2.985mL of DMSO (1.0mM) mother solution containing different surfactants and ions (sodium dodecylbenzenesulfonate (SDBS), sodium dodecylsulfate (SDS), Triton X-100, cetyl bromide Alkyltrimethylammonium (CTAB) and simple ions (such as: Na + ,K + ,Mg 2+ , Ca 2+ ,Zn 2+ NO 3 – , HCO 3 – , HCO 3 2– ,PO 4 3– , SO 4 2– )) in pure water, vortexed for 10 s, and measured fluorescence with a spectrofluorometer (excitation wavelength 334 nm). The result is as Figure 8 shown.

[0087] Figure 8 In the presence of different surfactants and ions, HBT-C 18 The ratio of the fluorescence emission intensity at 510nm and 450nm (I 510 / I 450 )Variety. The probe is highly sensitive to anionic surfactants with sulfonic acid groups, including: sodium dodecylbenzenesulfonate (SDBS), sodium dodecyl sulfate (SDS), and neutral Surfactant Triton X-100 and cationic surfactant ...

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Abstract

The invention relates to a fluorescent probe with an aggregation-induced emission (AIE) property and as shown in a general formula I, and a preparation method thereof, wherein R1 and R2 independently are hydrogen, C1-18 alkyl, halogen, C1-18 alkoxy, C1-18 alkyl sulfenyl, aryl and ceteroary; R3, R4 and R5 are C1-30 alkyl; R6 is an axial bond and C1-6 alkylene; and A<-> is an anion. The fluorescent probe can realize lighting detection of an anionic surfactant by forming an anion-cation aggregate in situ, and has high selectivity and high sensitivity on the anionic surfactant. In addition, the fluorescent probe can be applied to fluorescent dyeing of bacteria, and has the advantages of low background noise, high dyeing efficiency, no need of additional washing and the like. (The general formula I is as shown in the description).

Description

technical field [0001] The invention belongs to the field of surfactant detection, in particular to a method for detecting anionic surfactants. Background technique [0002] Anionic surfactants, especially alkyl sulfonates are the most important surfactants in commodities and are produced in large quantities, such as: sodium dodecylbenzenesulfonate (SDBS), sodium lauryl sulfate (SLS), lauryl sulfate (SLS), Sodium alkyl sulfate (SDS), etc. They are widely used as detergents, emulsifiers, foaming agents and dispersants in the cleaning, agricultural, cosmetic and pharmaceutical industries. Due to their wide application, their residues in water bodies may cause serious harm to the ecological environment, such as: inhibiting aquatic biological activity and accelerating the spread of oily pollutants. In addition, anionic surfactants may be irritating to human eyes and skin and cause inflammation. In order to make the detection of anionic surfactants even at home or in remote ar...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06C09K2211/1037G01N21/6428
Inventor 唐本忠高蒙秦安军王罗超
Owner SOUTH CHINA UNIV OF TECH
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