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Near-infrared two-region aggregation-induced emission fluorescent compound as well as preparation method and application thereof

A fluorescent compound and selected technology, applied in the field of biomedical fluorescence imaging applications, can solve problems such as luminescence quenching and difficulty in developing fluorescent aggregate nanoparticles

Active Publication Date: 2021-08-06
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when these large π-conjugated systems occur in the form of biologically useful aggregates or nanoparticles, strong intermolecular π-π interactions often lead to luminescence quenching.
The existence of this aggregation-induced fluorescence quenching (ACQ) effect made it difficult for them to develop bright fluorescent aggregates or nanoparticles for bioimaging

Method used

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  • Near-infrared two-region aggregation-induced emission fluorescent compound as well as preparation method and application thereof
  • Near-infrared two-region aggregation-induced emission fluorescent compound as well as preparation method and application thereof
  • Near-infrared two-region aggregation-induced emission fluorescent compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
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Embodiment approach

[0040] According to some embodiments of the present invention, the fluorescent compound has a structure represented by general formula (I):

[0041]

[0042] According to some embodiments of the present invention, R 1 and R 2 It is a hydrophobic steric hindrance group, which is used to ensure the deformation of the molecular conjugated skeleton.

[0043] According to a preferred embodiment of the present invention, R 1 and R 2 The same or different, and each independently selected from C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C4-C30 heteroaryl, C1-C30 alkoxy and -R 10 N(R 11 )R 12 .

[0044] According to a preferred embodiment of the present invention, R 1 and R 2 The same or different, and each independently selected from C1-C30 straight chain alkyl, C3-C30 branched chain alkyl, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C7-C30 Aralkyl, C7-C30 alkaryl, C4-C30 heteroaryl, C1-C30 alkoxy and -R 10 N(R 11 )R 12 .

[004...

Embodiment 1

[0180] Preparation of compound 2TT-oC26B

[0181]

[0182] In a 10ml test tube, add organotin compound (0.7g, about 1mmol) shown in formula (a1), dibromo-benzobisthiadiazole (87mg, about 0.25mmol) shown in formula (b), Pd 2 (dba) 3 (22mg, about 0.025mmol), P(o-tol) 3 (66 mg, about 0.21 mmol) and degassed dry toluene (1.5 mL), and seal with a cap to give a mixture. The mixture was stirred and heated to 130° C. for 48 h under a nitrogen atmosphere to obtain a crude product. After cooling the crude product was quenched with KF and extracted with DCM. The combined organic phases were washed with Na 2 SO 4 After drying and removing the solvent, the product was purified by a silica gel column to obtain a dark green solid (yield 35%). 1 H NMR (400MHz, CDCl 3 ),δ(ppm)=7.59-7.56(4H,m),7.31-7.29(10H,m),7.16-7.04(16H,m),2.59-2.57(4H,m),1.63(2H,m), 1.15-1.10(16H,m),0.73(12H,m). 13 C NMR (100MHz, CDCl 3), δ (ppm): 152.53, 146.81, 128.86, 128.70, 127.54, 126.12, 124.99, 123.94,...

Embodiment 2

[0184] Preparation of compound 2TT-oC610B

[0185]

[0186] The preparation method was the same as in Example 1, except that the organotin compound represented by formula (a1) was replaced by the organotin compound represented by formula (a2) (0.84 g, about 1 mmol) to obtain a dark green solid (50% yield). 1 H NMR (400MHz, CDCl 3 ), δ(ppm)=7.49-7.47(4H,m),7.33-7.29(10H,m),7.18-7.01(16H,m),2.79(4H,m),1.83(2H,m),1.23( 48H,m), 0.83(12H,m). 13 C NMR (100MHz, CDCl 3 ),δ(ppm):153.19,152.54,146.92,146.78,145.98,144.02,132.38,128.86,128.70,128.17,127.59,126.09,124.96,123.99,123.29,122.87,122.48,120.77,115.77,38.62,32.60,31.18 , 29.24, 28.86, 25.78, 22.07, 13.51. MS:m / z:[M]+calcd for C 82 h 96 N 6 S 4 :1292.6579,found:1292.6595. The fluorescence quantum yield was 11%.

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Abstract

The invention discloses a fluorescent compound which has a structure as shown in a general formula (I). The invention also discloses a preparation method of the compound and application of the compound in preparation of a diagnostic agent or an imaging agent for tumor detection and / or biological imaging such as in-vivo imaging. The fluorescent compound disclosed by the invention can emit fluorescence as high as 1600nm in an NIR-IIb region, wherein QY is as high as 9-18%. The compound has excellent imaging capability in superficial blood vessels and visceral organs of mice, has high resolution, and enhances the signal-to-noise ratio of an NIR-IIb region.

Description

technical field [0001] The invention relates to a near-infrared second region aggregation-induced luminescent fluorescent compound and a preparation method thereof, as well as its use in the field of biological imaging, belonging to the technical field of biomedical fluorescence imaging applications. Background technique [0002] Due to the advantages of high sensitivity, strong specificity, low cost, non-invasiveness, and no ionizing radiation, fluorescence imaging has attracted extensive attention in the fields of biomedicine, analytical chemistry, and materials science. Fluorescence imaging can be divided into three regions according to its emission wavelength: visible light region (400-700nm), near-infrared region 1 (NIR-I, 700-900nm) and near-infrared region 2 (NIR-II, 1000-1700nm). -II can also be subdivided into three sub-windows: NIR-IIa' (1000-1300nm), NIR-IIa (1300-1400nm) and NIR-IIb (1500-1700nm). Due to the suppression of molecular scattering and the minimizati...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06A61K49/00
CPCC07D513/04C09K11/06A61K49/0021C09K2211/1081C09K2211/1092C09K2211/1007C09K2211/1014
Inventor 唐本忠李媛媛钱骏
Owner THE HONG KONG UNIV OF SCI & TECH
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