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Azo aromatic compound, application thereof and reagent for enhancing Raman scattering signal

A technology of aromatic compounds and compounds, applied in the field of analytical chemistry, can solve problems such as interference with Raman signal detection, failure to provide Raman frequency adjustability, Raman signal cannot be accurately detected, etc., and achieve the effect of improving sensitivity

Pending Publication Date: 2022-07-01
HUAZHONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this research result cannot provide the tunability of the Raman frequency, and the signal molecule presents a strong fluorescent background when excited by electronic resonance, which interferes with the Raman signal detection at this time.
[0007] That is to say, when the excitation wavelength is close to the absorption wavelength of the compound, the electronic transition can increase the probability of Raman scattering and enhance the Raman signal, but the common problem caused by this is that when the excitation wavelength is near the absorption peak of the compound , the accompanying strong fluorescent background makes the Raman signal unable to be detected accurately

Method used

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  • Azo aromatic compound, application thereof and reagent for enhancing Raman scattering signal
  • Azo aromatic compound, application thereof and reagent for enhancing Raman scattering signal
  • Azo aromatic compound, application thereof and reagent for enhancing Raman scattering signal

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0099] Preparation Example 1: Synthesis of Group A Compounds (Core Groups are Diacetylenes)

[0100]

[0101] Add 3mL chloroform and 1mL of 1,4-dioxane to the 25mL single-neck flask, then weigh 3mmol of phenylacetylene and 1mmol of 4-ethynyl methyl benzoate and dissolve therein, add 0.05mmol of copper powder and 0.2 mmol tetramethylethylenediamine. The mixed system was placed at 50 °C and stirred for 12 h. Subsequently, 20 mL of dichloromethane was added, washed successively with saturated ammonium chloride, distilled water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After column chromatography, a yellow solid product A1.1. was obtained (yield 65 %) 1 H NMR (400MHz, CDCl 3 )δ7.99(d,J=8.3Hz,2H),7.55(d,J=8.3Hz,2H),7.39-7.30(d,J=8.3Hz,2H),6.65-6.54(d,J=8.3 Hz,2H),3.92(s,3H). 13 C NMR (101MHz, CDCl 3 )δ166.5,147.9,134.2,132.2,129.9,129.5,127.0,114.6,110.2,84.5,79.8,77.5,71.8,52.4.HRMS(ESI):calcd for C...

preparation example 2

[0106] Preparation Example 2: Synthesis of Group B Compounds (the core group is triacetylene)

[0107]

[0108] 9mL of chloroform and 3mL of 1,4-dioxane were added to a 50mL single-neck flask, followed by weighing trimethylsilylacetylene (15mmol, 3eq) and methyl 4-ethynylbenzoate (5mmol, 1eq) to dissolve To this, copper powder (0.25 mmol, 0.05 eq) and tetramethylethylenediamine (1 mmol, 0.2 eq) were added. The mixed system was placed at 50 °C and stirred for 12 h. Subsequently, 40 mL of dichloromethane was added, washed successively with saturated ammonium chloride, distilled water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After column chromatography, a pale yellow solid product 1 was obtained (yield 64%) . 1 H NMR (400MHz, Chloroform-d) δ8.03–7.91(m, 2H), 7.53(d, J=8.4Hz, 2H), 3.91(s, 3H), 0.23(s, 9H). 13 C NMR (101MHz, CDCl 3 )δ166.3,132.6,130.4,129.5,126.1,92.5,87.4,76.8,75.6,52.4,0.4.HRMS(ESI)...

preparation example 3

[0118] Preparation Example 3: Synthesis of Group C Compounds (the core group is tetraynes)

[0119]

[0120] Add 9mL chloroform and 3mL of 1,4-dioxane to the 50mL single-necked bottle, then weigh trimethylsilyl acetylene (15mmol) and 4-ethynylaniline (5mmol) and dissolve in it, add copper powder ( 0.25 mmol) and tetramethylethylenediamine (1 mmol). The mixed system was placed at 50 °C and stirred for 12 h. Subsequently, 40 mL of dichloromethane was added, washed with saturated ammonium chloride, distilled water and saturated brine successively, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After column chromatography, a brown-yellow solid product 6 was obtained (yield 60%) . 1 H NMR (400MHz, Chloroform-d)δ7.28(d,J=8.4Hz,2H),6.55(d,J=8.4Hz,2H),3.90(s,2H),0.21(s,9H). 13 C NMR (101MHz, CDCl 3 )δ147.7,134.3,114.6,110.1,89.5,88.5,78.1,72.4,0.3.HRMS(ESI):calcd for C 13 H 16 NSi + [M+H] + 214.10465, found214.10468.

[0121]...

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Abstract

The invention relates to the field of analytical chemistry, and discloses an azo aromatic compound and application thereof and a reagent for enhancing Raman scattering signals, and the compound has a structure as shown in a formula (I) or a formula (II). When the azo aromatic compound provided by the invention is used for enhancing a Raman scattering signal, the sensitivity is improved by more than 2-4 orders of magnitude, and the azo aromatic compound has frequency adjustability of 10 different spectral bands. Formula (I): Formula (II): Formula (I): Formula (II):

Description

technical field [0001] The invention relates to the field of analytical chemistry, in particular to an azo aromatic compound and its application and a reagent for enhancing Raman scattering signals. Background technique [0002] The development of modern spectroscopy and microscopy has pushed people to observe the dynamic process of molecular changes in living systems more sensitively and specifically. Specifically, the ability to directly observe a large number of different molecular species inside cells is particularly important for understanding complex systems and processes, while imaging many species with high sensitivity and selectivity at the cellular and subcellular levels remains challenging. Compared to other widely used imaging techniques, especially fluorescence imaging, Raman microscopy has emerged as a useful tool for multicolor live-cell imaging. [0003] Due to the inherent nature of molecular vibrations coupled to incident light, the Raman signal provides c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C07C255/65C07D455/04C07D519/00G01N21/65
CPCC07C245/08C07C255/65C07D455/04C07D519/00G01N21/658
Inventor 唐浴尘高婷娟张礼知
Owner HUAZHONG NORMAL UNIV
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