IR780 ketone form cyanine dye molecule, and preparation method and crystal structure thereof
A technology of crystal structure and cyanine dyes, applied in the field of fluorescent dyes, can solve the problems of low purity, many by-products, difficult separation and purification, etc., and achieve the effects of high yield, stable crystal structure and simple synthesis method
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Embodiment 1
[0039] The synthesis of IR780 ketocyanine dye molecule, see the specific synthetic route figure 1 .
[0040] S1. Preparation of compound 5: Under nitrogen protection ice bath condition, take 20mL of N,N-dimethylformamide (273mmol) and dissolve in dichloromethane, slowly add 20mL of POCl3 (17.5mL, 115mmol) di Chloromethane solution. After stirring for 30 minutes, 5 g of cyclohexanone (50 mmol) was added, then the temperature was raised to 80° C., and the reaction mixture was heated to reflux for 3 hours. After the reaction, the mixture was poured into ice water, left overnight, and filtered with suction to obtain compound 5 (8.0 g) as a yellow solid with a yield of 92%.
[0041] S2. Preparation of Compound 4: Dissolve 9.82 mL of phenylhydrazine (0.1 mmol) and 12 mL of 3-methyl-2-butanone (0.11 mL) in a mixture of 30 mL of absolute ethanol and 3 drops of acetic acid, and heat to reflux After 4 hours, cool to room temperature, remove the solvent under reduced pressure, then ad...
Embodiment 2
[0046] The crystal structure of IR780 ketocyanine dye molecule 1: the crystal was obtained by dichloromethane and ether diffusion method, and its crystal structure was tested by X-ray diffraction single crystal tester to obtain its single crystal structure data. For relevant data, see Tables 1-3, and for relevant spectra, see Figure 5-7 .
[0047] Table 1. Basic parameters of the crystal structure of IR780 ketocyanine dye molecule 1
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[0050] Table 2. The bond length and bond angle of the crystal structure of IR780 ketocyanine dye molecule 1
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[0055] Symmetry transformations used to generate equivalent atoms:
[0056] Table 3. Hydrogen bond data of the crystal structure of IR780 ketocyanine dye molecule 1
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[0058] Symmetry transformations used to generate equivalent atoms:
[0059] #1x,-y+1 / 2,z+1 / 2
Embodiment 3
[0061] The ultraviolet spectrum of IR780 ketocyanine dye molecule 1 in the aqueous solution system: CH3OH:HEPES (0.01mol / L, pH=7.4) = 9:1 (v:v) mixed solvent was used as the test system for the ultraviolet spectrum.
[0062] Dissolve IR780 ketocyanine dye molecule 1 in a solvent of CH3OH:HEPES=9:1 (v:v) and set the volume to a 100mL volumetric flask to prepare a solution with a concentration of IR780 ketocyanine dye molecule 1 of 10 μmol / L .
[0063] Add 5 mL of CH3OH:HEPES ((0.01mol / L, pH=7.4)=9:1 (v:v) solution of IR780 ketocyanine dye molecule 1 with a concentration of 10 μmol / L to the sample bottle, and let it stand for 3 minutes , transfer the test solution to a standard quartz cuvette of 1cm×1cm, and measure its ultraviolet spectrum.
[0064] The UV spectrum of IR780 ketocyanine dye molecule 1 is as follows Figure 8 shown.
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