Organic molecular probe material with nucleus-shell structure and preparation method thereof

A technology of organic molecules and shell structures, applied in the direction of luminescent materials, material excitation analysis, chemical instruments and methods, etc., can solve the problems of background luminescence interference and weak penetrating power, achieve stable fluorescence luminescence performance, strengthen ligand exchange, Apply a wide range of effects

Inactive Publication Date: 2009-12-16
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these materials have some insurmountable defects in chemical fluorescent labeling and in vivo imaging, such as: organic dyes are easy to be bleached and oxidatively metabolized in vivo, and their excitation spectra are often in the high-energy region, resulting in weak penetration and background luminescence Serious interference; inorganic cadmium quantum dots have certain application limitations due to the eventual metabolism of toxic ions such as cadmium and selenium

Method used

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  • Organic molecular probe material with nucleus-shell structure and preparation method thereof
  • Organic molecular probe material with nucleus-shell structure and preparation method thereof
  • Organic molecular probe material with nucleus-shell structure and preparation method thereof

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Embodiment 1

[0035] 1) Transition metal complex Re(phen)(CO) 3 Cl is the synthesis of 3-{2-[9,9-bis[6-(N-carbazolylhexyl)fluorenyl]]}-phenyl-phenanthroline tricarbonyl rhenium chloride:

[0036] 422 mg (0.5 mmol) and Re(CO) 3 Cl 181mg (0.5mmol) was added to 50mL toluene, refluxed for 12 hours, the solvent was evaporated, and then the residue was chromatographed on a silica gel column with dichloromethane as the elution meter to obtain the transition metal complex Re(phen )(CO) 3 Cl 390 mg, yield 68%. 1 H NMR (400MHz, CDCl 3 , TMS) δ = 9.59 (d, J = 1.6Hz, 1H), 9.40 (d, J = 4.4Hz, 1H), 8.52 (t, J = 3.4Hz, 2H), 8.03 (dd, J = 3.6Hz, 7.6Hz, 4H), 7.95(dd, J=8.8Hz, 15.2Hz, 2H), 7.86(d, J=7.6Hz, 1H), 7.83(t, J=8.0Hz, 1H), 7.76(d, J =7.2Hz, 1H), 7.68(d, J=8.0Hz, 1H), 7.64(s, 1H), 7.38(t, J=8.0Hz, 5H), 7.32(t, J=7.2Hz, 1H), 7.28(d, J=8.4Hz, 5H), 7.16(t, J=7.4Hz, 4H), 4.15(t, J=7.2Hz, 4H), 2.10-1.93(m, 4H), 1.68(t, J =6.4Hz, 4H), 1.20-1.12(m, 8H), 0.65-0.61(m, 4H), 13 C NMR (75MHz, CDCl 3, T...

Embodiment 2

[0042] 1) Transition metal complex Ru(bpy) 3 (PF 6 ) 2 Namely three {5-[2-[9,9-bis[6-(N-carbazolylhexyl)fluorenyl]]]-phenyl-2,2'-bipyridyl} divalent ruthenium hexafluorophosphate Synthesis of salt:

[0043] 169.5 mg (0.3 mmol) of 5-[2-[9,9-bis[6-(N-carbazolylhexyl)fluorenyl]]]-phenyl-2,2'-bipyridine and [Ru(DMSO ) 4 ]Cl 2 Add 48.5mg (0.1mmol) into 20mL ethanol solution, reflux for 24 hours under dark conditions; then add 80mg KPF 6 (80 mg) continued to reflux for 2 hours; after cooling to room temperature, 30 milliliters of water was added, the precipitated product was filtered out, and washed twice with 5 milliliters of water; then silica gel column chromatography was used to elute the product with dichloromethane containing 3% acetone , after vacuum drying, 104 mg of transition metal complex Ru(bpy) in the form of red solid powder can be obtained 3 (PF 6 ) 2 . MS (MALDI-ToF): m / z 1941.2. 1 H NMR (500MHz, CDCl3): 8.62 (bs, 3H, PyH), 8.55 (bs, 3H, PyH), 8.01 (bs, 3...

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Abstract

The invention relates to an organic molecular probe material with a nucleus-shell structure. A core is transition metal complex; a shell layer is an amphiphilic polymer; metal ion is Ru2+ (ruthenium), Os2+ (osmium) or Re+ (rhenium); the ligands are monosubstitution or polysubstituted morpholine and monosubstitution or polysubstituted 2,2'-bipyridyl; and the amphiphilic polymer is a copolymer formed by polyethylene glycol methacrylate and dimethylamino ethyl methacrylate. The organic molecular probe material has the advantages that the organic molecular probe material has the nucleus-shell structure, wraps a fluorescent material of the transition metal complex in the amphiphilic polymer, is favorable for strengthening the ligand exchange in environment of resisting complex cells by the fluorescent material and rapid oxidative metabolism of cells on the fluorescent material, thereby stabilizing the fluorescence luminous performance of the ligand; and the spherical luminous nano-particles has the function of transfecting implanted fluorescent protein gene plasmid, and realizes dual-marking function of rapid timely trace labeling and long-term trace marking, so the spherical luminous nano-particle has wider application.

Description

【Technical field】 [0001] The invention relates to a molecular probe material in fluorescence imaging technology, in particular to an organic molecular probe material with a core-shell structure and a preparation method thereof. 【Background technique】 [0002] The emergence of molecular imaging technology is attributed to many factors such as the development of molecular biology and cell biology, highly specific fluorescent molecular labeling probes, and the development of cell imaging equipment. In recent years, fluorescence imaging technology has become a hotspot in the current study of cell biology due to its advantages of intuition, diverse labeling targets, low cost and simple operation. Many traditional organic dyes, such as fluorescein derivatives, rhodamine, cyanine, fluorescein (BODIPY) series derivatives and some rare earth complexes and inorganic quantum dots have been widely used as fluorescent probe molecules for chemical labeling methods. In cell imaging resear...

Claims

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Application Information

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IPC IPC(8): C09K11/02C09K11/06G01N21/64
Inventor 曾宪顺刘磊
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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