A near-infrared organic supramolecular assembly and its preparation method and application
A supramolecular assembly and supramolecular polymer technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of fluorescence self-quenching, fluorescence reduction, disappearance, etc., to increase fluorescence intensity and increase biocompatibility. , the effect of increasing water solubility
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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] 0.6 mmol of 9,10-bis((E)-4-bromostyrene)anthracene (0.33 g), 2.4 mmol of pyridin-4-ylboronic acid (0.29 g) were added to 48 mL of toluene, and 0.03 mmol of catalytic Amount of Pd (PPh 3 ) 4 (35mg) in N 2 Stir in the atmosphere for 15min, then add 6mL of K with a concentration of 0.8M 2 CO 3 The aqueous solution and 6 mL of ethanol were mixed uniformly, and the reaction was continuously refluxed for 6.5 h in a nitrogen atmosphere, cooled to room temperature, washed three times with deionized water, and the organic layer was extracted with ethyl acetate and anhydrous MgSO 4 Dry, place the precipitate to be dried in a vacuum drying oven, and use column chromatography to obtain a product with a higher purity, wherein the eluent is dichloromethane (CH 2 Cl 2 ) and ethanol (9:1 by volume) w...
Embodiment 2
[0060] Example 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 -benzylpyridine-1-onium)bromide (DSA-(Py + -CH 2 -ph) 2 ):
[0062]
[0063] 9,10-bis((E)-4-(pyridin-4-yl)styryl)anthracene (2Py-DSA) was added to a mixed solvent of DMF and THF (the volume ratio of DMF to THF was 1:1) , the mixture was heated to reflux until the solution turned orange, and benzyl bromide (0.2 mL, 1.6 mmol) was added dropwise until the solution turned red, and the temperature was raised to 90 °C for 6 h. The yellow precipitate was filtered, washed with ethanol and ether, and the solid product was recrystallized in ethanol and acetone to give a 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),8.64(d,J=6.8Hz,1H),8.47–8.40(m,2H),8.22(d,J=8.5Hz,1H),8.12( d, J=8.5Hz, 1H), 7.64-7.57(m, 2H), 7.4...
Embodiment 3
[0066] Preparation of DSA-(Py + -CH 2 -ph) 2 With the assembly of cucurbit[7] urea (hereinafter referred to as CB[7]) and cucurbit[8] urea (hereinafter referred to as CB[8]) in different proportions, 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] One equivalent of DSA-(Py + -CH 2 -ph) 2 and 2 equivalents of CB[7] were fully assembled in methanol-containing aqueous solution, a large amount of solvent was removed by rotary evaporation, dried in a vacuum drying oven, and then dried 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] converts 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] One equivalent of DSA-(Py + -CH 2 -ph) 2 and 4 equivalents of CB[7] were fully assembled in methanol-containing aqueous solution, a large amount of solvent was ...
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