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Application of polymer microspheres to Raman detection

A technology of polymers and amide polymers, applied in the application field of polymer microspheres in the field of bioimaging, which can solve the problems of poor reproducibility and difficult quantitative analysis, and achieve the effect of uniform particle size and stable structure

Active Publication Date: 2017-11-21
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the strong signal of the SERS probe depends on the enhancement effect of the metal substrate, and there are problems such as poor reproducibility and difficult quantitative analysis.

Method used

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  • Application of polymer microspheres to Raman detection
  • Application of polymer microspheres to Raman detection
  • Application of polymer microspheres to Raman detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1. Synthesis of compound m-1 monomer

[0053]

[0054] The raw material butynyl alcohol (700 mg, 10 mmol) was dissolved in 20 mL of anhydrous DCM, 4.15 mL (30 mmol) of dry TEA was added, and N 2 For protection, methacryloyl chloride (1.65 mL, 17 mmol) was added dropwise to the solution under ice-cooling. After the dropwise addition was completed, it was moved to normal temperature for 6 h. The reaction solution was extracted with DCM, saturated NaHCO 3 The solution was washed twice, and the saturated NaCl solution was washed once. Anhydrous Na for organic phase 2 SO 4 Dry, filter, concentrate, and use PE and DCM as eluents (volume ratio 1:2) for column purification to obtain 940 mg of monomer m-1 as a colorless oily liquid. The yield was 68.1%.

[0055] 1 H NMR (400MHz, CDCl 3 )δ6.14(s,1H),5.58(s,1H),4.25(t,J=6.8Hz,2H),2.57(td,J=6.8,2.7Hz,2H),1.95(s,3H).

[0056] 13 C NMR (101MHz, CDCl 3 )δ167.29, 136.25, 126.04, 80.20, 70.02, 62.49, 19.16, 18.42...

Embodiment 2

[0057] Embodiment 2. the synthesis of compound m-2 monomer

[0058]

[0059] The raw material 2 pentyn-1-ol (840 mg, 10 mmol) was dissolved in 20 mL of anhydrous DCM, 4.15 mL (30 mmol) of dry TEA was added, and N 2 For protection, methacryloyl chloride (1.65 mL, 17 mmol) was added dropwise to the solution under ice-cooling. After the dropwise addition was completed, it was moved to normal temperature for 6 h. The reaction solution was extracted with DCM, saturated NaHCO 3 The solution was washed twice, and the saturated NaCl solution was washed once. Anhydrous Na for organic phase 2 SO 4 It was dried, filtered, concentrated, and purified by column using PE and DCM as eluents (volume ratio 1:2) to obtain 1.23 g of monomer m-2 as a colorless oily liquid. The yield was 80.9%.

[0060] MS[M+Na] + : measured value: 175.2; C 9 h 12 o 2 Theoretical value: 175.08.

[0061] 1 H NMR (400MHz, CDCl 3 )δ6.15(s,1H),6.15(s,1H),5.64–5.54(m,1H),5.62–5.57(m,1H),4.73(s,2H),4.73(s,...

Embodiment 3

[0063] Embodiment 3. the synthesis of compound m-3 monomer

[0064]

[0065] The raw material trimethylsilyl propynol (1.28 g, 10 mmol) was dissolved in 20 mL of anhydrous DCM, 4.15 mL (30 mmol) of dry TEA was added, and N 2 For protection, methacryloyl chloride (1.65 mL, 17 mmol) was added dropwise to the solution under ice-cooling. After the dropwise addition was completed, it was moved to normal temperature for 6 h. The reaction solution was extracted with DCM, saturated NaHCO 3 The solution was washed twice, and the saturated NaCl solution was washed once. Anhydrous Na for organic phase 2 SO 4 Dry, filter, concentrate, and use PE and DCM as eluents (volume ratio 1:2) for column purification to obtain 1.22 g of monomer m-3 as a colorless oily liquid. The yield was 62.2%.

[0066] 1 H NMR (400MHz, CDCl 3 )δ6.17(s,1H),5.63–5.58(m,1H),4.75(s,2H),1.96(s,3H),0.18(s,9H).

[0067] 13 C NMR (101MHz, CDCl 3 )δ166.70, 135.89, 126.49, 99.27, 92.08, 53.10, 18.42.

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Abstract

The invention discloses application of polymer microspheres to Raman detection. Methacrylate / amide polymer monomers or styrene polymer monomers containing alkynyl, cyano, azido or a carbon-deuterium bond group are prepared into the polymer microspheres with the particle diameter from a nanometer grade to a micron grade through an emulsion polymerization or dispersion polymerization method; the polymer microspheres have a remarkable Raman signal under the condition of no metal sensitization structure; and a Raman characteristic peak signal is located in a Raman quiet zone (1800cm<-1> to 2800cm<-1>) in a living organism and can be used as a marker for biological imaging.

Description

technical field [0001] The invention relates to Raman spectroscopy technology, in particular to the application of a polymer microsphere with Raman effect in the field of biological imaging. Background technique [0002] Raman spectroscopy is a non-destructive spectroscopy technology based on the inelastic scattering of photon-excited vibrations. It has fingerprint identification characteristics and can obtain the structure and composition information of substances from the molecular level. Compared with fluorescent probes, Raman probes have the advantages of near-infrared excitation, narrow spectrum, and photostability, which make them quickly applied to probes, cell imaging, and in vivo imaging. However, the inherently weak signal of Raman scattering leads to too low detection limit, which always limits the further development and application of Raman spectroscopy. Scientists are always looking for better ways to obtain stronger Raman signals and lower detection limits. ...

Claims

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Application Information

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IPC IPC(8): C07C69/533C07F7/08C07C205/42C07C255/14C07C255/55C07C247/04C07C247/16G01N21/65C08F220/40C08F230/08C08F220/34C08F212/34C08F212/14
CPCC07C69/533C07C205/42C07C247/04C07C247/16C07C255/14C07C255/55C07F7/08C08F212/14C08F212/34C08F220/34C08F220/40C08F230/08G01N21/65C08F222/102
Inventor 汤新景金庆庆
Owner PEKING UNIV
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