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Near-infrared two-region aggregation-induced emission molecule and application thereof

A molecular and rotor technology used in the field of near-infrared second region fluorescence imaging

Pending Publication Date: 2022-02-18
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obtaining high quantum yields of near-infrared fluorescent molecules using AIE molecular design principles remains a challenge so far

Method used

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  • Near-infrared two-region aggregation-induced emission molecule and application thereof
  • Near-infrared two-region aggregation-induced emission molecule and application thereof
  • Near-infrared two-region aggregation-induced emission molecule and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Example 1: Compound Synthesis

[0150] Synthetic roadmap of 2TT-oC6B:

[0151]

[0152] Synthesis of compound 2TT-oC6B

[0153] To synthesize compound 2TT-oC6B, to a 10 mL tube were added organotin (1, 0.7 g, 1 mmol), dibromo-BBT (2, 87 mg, 0.25 mmol), Pd 2 (dba) 3 (22mg, 0.025mmol), P(o-tol) 3 (66 mg, 0.21 mmol) and degassed dry toluene (1.5 mL) and sealed with a Teflon cap. in N 2 Under atmosphere, the reaction mixture was heated to 130°C with stirring for 48 hours. After cooling, the crude product was quenched with potassium fluoride (KF) solution, extracted with dichloromethane (DCM), and washed with Na 2 SO 4 The combined organic phases were dried. After removal of the solvent, the product was purified with a silica gel column to give a dark green solid (35% yield). 1 H NMR (400MHz, CDCl 3 ), δ(ppm)=7.59-7.56(4H,m), 7.37(2H,s), 7.31-7.26(8H,m), 7.16-7.12(8H,m), 7.11-7.03(8H,m), 2.61-2.57(4H,t,J=8Hz),1.63,(4H,m),1.15-1.10(12H,m),0.73(6H,m). 13 C NMR (...

Embodiment 2

[0161] Example 2: Fabrication of AIE Nanoparticles (AIE-dot)

[0162] A mixture of compounds 2TT-oC6B, 2TT-mC6B or 2TT-m,oC6B (1 mg), DSPE-polyethylene glycol 2000-maleimide (1.5 mg) and tetrahydrofuran (THF) (1 mL) was sonicated ( 12W output, XL2000, Misonix Incorporated, NY) to obtain a clear solution. The solution was quickly poured into 9 mL of water and vigorously sonicated in the water for 2 minutes. The mixture was then stirred in a fume hood for 12 hours to remove THF. The AIE nanoparticle suspension was ultrafiltered (molecular weight cutoff 100 kDa) at 3000 xg for 30 minutes. It was found that compounds 2TT-oC6B, 2TT-mC6B or 2TT-m,oC6B were successfully encapsulated into DSPE-polyethylene glycol 2000-maleimide matrix in the form of AIE nanoparticles.

Embodiment 3

[0163] Example 3: Determination of Dye Fluorescence Quantum Yield (QY)

[0164] The QY of the dye was measured using the NIR-II type fluorescent IR-26 dye as a reference (QY=0.5%). For reference calibration, IR-26 in 1,2-dichloroethane (DCE) was diluted to a DCE solution to prepare five samples with absorbance values ​​at 808 nm of ~0.1, ~0.08, ~0.06, ~0.04, and ~0.02 because these highly diluted samples minimize secondary optical processes such as reabsorption and reemission effects. Then, a total of five concentrations of linearly spaced solutions of IR-26 in DCE were transferred into 10 mm path fluorescent tubes at one time. The excitation source was an 808 nm diode laser. The emission light was filtered with a 900 nm long pass to exclude other light interference, and the emission spectrum in the 900 nm to 1500 nm region was acquired. For DCE and H 2 The same was done for AIE dyes in O. Then, all emission spectra of the reference and sample were integrated in the NIR-I...

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Abstract

The invention relates to the design of organic fluorescent materials, in particular to a small molecular fluorescent compound with polymerization-induced emission characteristics, which can display emitted light in a second near-infrared window (1000-1700 nm) and can provide imaging for deep tissues at an ultrahigh signal-to-noise ratio. For example, neutrophils carrying the compounds of the invention can penetrate the brain, and inflammation located deep in brain tissue can be observed through the intact scalp and skull.

Description

technical field [0001] The present invention relates to the development of organic fluorescent materials, in particular to a class of molecules with polymerization-induced luminescence properties, and the use of the molecules for near-infrared second region (1000nm-1700nm) fluorescence imaging. Background technique [0002] Fluorescence imaging with high spatiotemporal resolution and sensitivity provides a powerful tool for direct visualization of dynamic biological processes. Fluorescent molecules capable of emitting light in the near-infrared second region (NIR-II, 1000nm–1700nm) show significant advantages of deeper tissue penetration, higher spatial resolution, and better signal-to-noise Light scattering and autofluorescence in tissue are reduced at longer wavelengths. Therefore, near-infrared fluorescence imaging holds great promise for accurate diagnosis of deep diseases. [0003] Although deep diseases such as brain tumors can be observed using fluorescent molecules...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06C07K14/16C12N5/0787G01N21/64
CPCC07D513/04C09K11/06C07K14/005C12N5/0642G01N21/6458C09K2211/1081C09K2211/1092C12N2740/16022
Inventor 唐本忠刘顺杰丁丹
Owner THE HONG KONG UNIV OF SCI & TECH
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