Near-infrared organic supramolecular assembly as well as preparation method and application thereof

A supramolecular assembly, supramolecular polymer technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of fluorescence self-quenching, fluorescence reduction, quenching, etc., and achieve increased fluorescence intensity and biocompatibility. Increased and reduced biotoxicity effects

Active Publication Date: 2021-08-20
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Organic light-emitting materials have attracted much attention because of their broad application prospects in biosensors, fluorescent probes, cell imaging, light-emitting diodes, etc. Traditional organic light-emitting molecules have aggregation-induced fluorescence quenching (Aggregation-Caused Quenching, ACQ) The defect is that it has a high fluorescence quantum yield in a dilute solution, but the fluorescence is greatly reduced or even disappeared in a high concentration or in a solid state. Long-wavelength light-emitting compounds, that is, near-infrared light-emitting compounds, are more prone to self-quenching of fluorescence in a solid state. However, due to the strong penetrability of near-infrared light to biological tissues, less photodamage, and better spatial resolution, the development of solid-state organic materials with near-infrared luminescence has been a research hotspot in this field.

Method used

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  • Near-infrared organic supramolecular assembly as well as preparation method and application thereof
  • Near-infrared organic supramolecular assembly as well as preparation method and application thereof
  • Near-infrared organic supramolecular assembly as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Preparation of distyryl anthracene derivatives 2Py-DSA and 2Py + -DSA

[0053] Synthesis of 9,10-bis((E)-4-(pyridin-4-yl)styryl)anthracene (2Py-DSA):

[0054]

[0055] Add 0.6mmol of 9,10-bis((E)-4-bromostyrene)anthracene (0.33g), 2.4mmol of pyridin-4-ylboronic acid (0.29g) into 48mL of toluene, and then add 0.03mmol of catalytic Amount of Pd(PPh 3 ) 4 (35mg), in N 2 Stir in the atmosphere for 15min, then add 6mL of 0.8M K 2 CO 3 The aqueous solution and 6 mL of ethanol were mixed evenly, and after continuous reflux reaction in a nitrogen atmosphere for 6.5 h, cooled to room temperature, washed with deionized water three times, and the organic layer was extracted with ethyl acetate and washed with anhydrous MgSO 4 Drying, the precipitate was placed in a vacuum drying oven to dry, and the product with higher purity was obtained by column chromatography, wherein the eluent was dichloromethane (CH 2 Cl 2 ) and ethanol (volume ratio of 9:1), with CH 2 ...

Embodiment 2

[0060] Embodiment 2. Preparation of distyryl anthracene derivatives DSA-(Py + -CH 2 -ph) 2

[0061] Synthesis of (4,4'-(((1E,1'E)anthracene-9,10-diylbis(ethylene-2,1-diyl))bis(4,1-phenylene))bis(1 -Benzylpyridin-1-ium) bromide (DSA-(Py + -CH 2 -ph) 2 ):

[0062]

[0063] Add 9,10-bis((E)-4-(pyridin-4-yl)styryl)anthracene (2Py-DSA) into a mixed solvent of DMF and THF (the volume ratio of DMF and THF is 1:1) , the mixture was heated to reflux until the solution was orange, and (0.2mL, 1.6mmol) benzyl bromide was added dropwise until the solution turned red, and the temperature was raised to 90°C for 6h. After the reaction system produced a large amount of orange precipitate, it was cooled to room temperature. The yellow precipitate was filtered, washed with ethanol and ether, and the solid product was recrystallized in ethanol and acetone to obtain brown-red powder DSA-(Py + -CH 2 -ph) 2 0.14 g, 81% yield.

[0064] 1 H NMR (400MHz, DMSO-d 6 )δ9.24(d, J=6.8Hz, 1H)...

Embodiment 3

[0066] Preparation of DSA-(Py + -CH 2 -ph) 2 Assemblies with different proportions of cucurbit [7] urea (hereinafter referred to as CB [7]) and cucurbit [8] urea (hereinafter referred to as CB [8]), the specific steps are as follows:

[0067] test(DSA-(Py + -CH 2 -ph) 2 ) in DMSO-d 6 middle 1 H NMR (400MHz) spectrum;

[0068] 1 equivalent of DSA-(Py + -CH 2 -ph) 2 and 2 equivalents of CB[7] were fully assembled in an aqueous solution containing methanol, and a large amount of solvent was removed by rotary evaporation, then dried in a vacuum oven, and then washed with 30% d 6 -DMSO and 70% D 2 O mixed solvent to dissolve it, test its 1 H NMR (400MHz) spectrum (see figure 2 ), CB[7] will DSA-(Py + -CH 2 -ph) 2 The e, f, g, h sites on the package are wrapped to get 2Py + -DSA+2CB[7] assembly;

[0069] 1 equivalent of DSA-(Py + -CH 2 -ph) 2 and 4 equivalents of CB[7] were fully assembled in an aqueous solution containing methanol, a large amount of solvent wa...

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Abstract

The invention relates to an organic supramolecular assembly which comprises a compound A and a compound B. The compound A is a stilbene anthracene derivative; the compound B is cucurbit [7] uril and / or cucurbit [8] uril. The preparation method of the assembly is simple, solid-state near-infrared luminescence of organic molecules can be achieved, and the assembly has good water solubility and biocompatibility and can be used for biological imaging, photodynamic diagnosis and treatment and the like.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a near-infrared organic supramolecular assembly and its preparation method and application. Background technique [0002] Organic light-emitting materials have attracted much attention because of their broad application prospects in biosensors, fluorescent probes, cell imaging, light-emitting diodes, etc. Traditional organic light-emitting molecules have aggregation-induced fluorescence quenching (Aggregation-Caused Quenching, ACQ) The defect is that it has a high fluorescence quantum yield in a dilute solution, but the fluorescence is greatly reduced or even disappeared in a high concentration or in a solid state. Long-wavelength light-emitting compounds, that is, near-infrared light-emitting compounds, are more prone to self-quenching of fluorescence in a solid state. However, due to the strong penetrability of near-infrared light to biological tissues, le...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C09K11/06
CPCC08G83/008C09K11/06C09K2211/1416C09K2211/1466
Inventor 曾毅尹文霞李嫕陈金平于天君
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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