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Preparation of near-infrared fluorescent probe with PTT effect and aggregation-induced emission enhancement effect

A technology of aggregation-induced luminescence and fluorescent probes, applied in luminescent materials, phototherapy, organic chemistry, etc., can solve problems that hinder the application of fluorescent dyes, and achieve good photothermal conversion performance, good photostability and photobleaching resistance Effect

Active Publication Date: 2020-04-14
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This ACQ phenomenon seriously hinders the application of fluorescent dyes in many applications such as optoelectronics and bioimaging.

Method used

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  • Preparation of near-infrared fluorescent probe with PTT effect and aggregation-induced emission enhancement effect
  • Preparation of near-infrared fluorescent probe with PTT effect and aggregation-induced emission enhancement effect
  • Preparation of near-infrared fluorescent probe with PTT effect and aggregation-induced emission enhancement effect

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthesis of probe IR780-O-TPE, the synthetic route diagram is as follows figure 2 .

[0024] Concrete synthetic steps:

[0025] Add IR-780 iodide (20 mg, 0.03 mmol), 1,2-diphenyl-1,2-bis(4-hydroxybenzene)ethylene (40.0 mg 0.11 mmol) to a 10 mL two-necked bottle, vacuum-nitrogen Replace 3 times, then add 2 mL of anhydrous DMF and 0.2 mL of anhydrous triethylamine with a syringe. Under the protection of nitrogen, heat to 85 ° C for 5 h, TLC detection of the reaction, after the reaction is complete, without other treatment, the solvent is directly evaporated to dryness by the oil pump, the crude product is separated by a silica gel flash column, and CH 2 Cl 2 :CH 3 OH=20:1 eluent was eluted to obtain 20 mg dark green solid with a yield of about 80%. 1 H NMR (400 MHz, CDCl 3 ): δ 7.92 (d, 2H), 7.55(d, 2H), 7.35(t, 2H), 7.27–7.24 (m, 3H), 7.18 (t, 2H), 7.12−7.01 (m, 17H), 6.12 (d, 2H), 4.09 (t, 4H), 2.76 (t, 4H), 2.08 (t, 2H), 1.90-1.85 (m, 4H), 1.35 (s, 12H), 1...

Embodiment 2

[0027] UV-visible absorption spectrum: prepare 10 μM ethanol solution of IR780-O-TPE and IR-780 iodide, and scan the UV-visible spectrum at 300–900 nm, the results are as follows image 3 .

Embodiment 3

[0029] AIEE property test: IR780-O-TPE is easily soluble in ethanol, but insoluble in n-hexane. Weigh an appropriate amount of IR780-O-TPE on a ten-thousandth analytical balance, add an appropriate amount of ethanol to dissolve, and make the concentration 1 mM as the mother solution. Use a pipette gun to draw 10 μL of the mother solution into the EP tube, add ethanol in proportion, and then, under vibration, add the solution into n-hexane to prepare n-hexane containing ƒ h 90%, 70%, 50%, 30%, 10%, and 0% ethanol / n-hexane mixed solution, so that the final concentration of the solution was 10 μM, and the prepared mixed solution was left at room temperature for 1 h, and the fluorescence spectrum was measured. Such as Figure 4 .

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PUM

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Abstract

The invention discloses preparation of a near-infrared fluorescent probe with a PTT effect and an aggregation-induced emission enhancement effect, wherein the fluorescent probe is formed by linking atraditional fluorescent nuclear IR-780 iodide with near-infrared excitation and emission and an aggregation-induced emission molecule TPE through an oxygen ether bond. Compared with the IR-780 iodide,the probe of the invention has the significantly enhanced fluorescence intensity in an ethanol solution, shows a typical AIEE effect in a mixed solvent, can selectively generate photo-thermal killingeffects on various cancer cells at a concentration of 0.3 [mu]M, has no obvious killing effect on normal cells at a concentration of 0.3 [mu]M, and has remarkable killing selectivity. According to the invention, the probe is simple to prepare, has good light stability and good photo-thermal conversion capability, has excitation and emission in a near-infrared region, is less in background interference and damage to organisms, has diagnosis and treatment integrated function and is expected to be applied to clinical research.

Description

technical field [0001] The invention belongs to the technical field of fluorescent biological diagnosis and treatment, and specifically relates to the preparation of a class of near-infrared fluorescent probes with PTT effect and aggregation-induced luminescence enhancement effect. Background technique [0002] In optical imaging technology, near-infrared (NIR) fluorescence imaging in the wavelength range (700–1000 nm) has attracted extensive attention due to its excellent performance. Because organisms and tissues have lower absorption and autofluorescence in this area, and less scattering of near-infrared light, background interference can be reduced and sensitivity can be improved. At the same time, near-infrared light has strong penetrability in tissue cells , with less photodamage to cells. [0003] Traditional fluorescent dyes usually contain a conjugated planar structure, and the fluorescence brightness is very strong in a dilute solution or in a monodisperse state, ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/12A61N5/06
CPCC09K11/06C07D209/12A61N5/0601C09K2211/1029C09K2211/1007A61N2005/0612
Inventor 孟萌赵秀杰郗日沫陈韵邓川
Owner NANKAI UNIV
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