Organoboron compound based on acylhydrazone ligands and its preparation method and application
A compound and organoboron technology, applied in the field of detection and analysis, can solve problems such as poor sensitivity and poor stability of lipid droplet labeling probes, and achieve good AIE characteristics and good thermal stability.
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Embodiment 1
[0086] Embodiment 1: the preparation of product
[0087](1) Synthesis of DMA-POABP
[0088] In a 100mL single-necked round bottom bottle equipped with a condenser, add 4-dimethylaminobenzaldehyde (4-dimethylaminobenzaldehyde, DMA-P-CHO; 1.5g, 10mmol), benzohydrazide (BHA; 1.36g , 10mmol) and ethanol (EtOH; 20mL) solvent, heated to reflux for 24 hours. After the reaction mixture was cooled back to room temperature, it was filtered and rinsed three times with cold ethanol solvent to obtain a white DMA-PAHP intermediate solid product, which was directly carried out to the next reaction without further purification after vacuum drying. In a 100mL double-necked round bottom bottle equipped with a condenser, add DMA-PAHP allyltrimethylsilane (ATMS; 2.05mL, 12.9mmol), boron trifluoride diethyl ether (BF 3 OEt 2 1.87mL, 14.87mmol) and dry dichloroethane (DCE; 50mL) solvent, after heating to reflux for more than two hours, the reaction was monitored with a silica gel plate (TLC); af...
Embodiment 2
[0100] Example 2: Research on Optical and Aggregation-Induced Luminescent Properties of Products
[0101] Two organoboron fluorescent products (DMA-POABP and POABP-DMA) are taken as examples to illustrate their optical properties and aggregation-induced luminescent properties. The same is true for other products, and details will not be repeated here.
[0102] (1) Research on optical properties
[0103] The ultraviolet-visible (UV-vis) absorption spectra and photoluminescence (PL) spectra of DMA-POABP and POABP-DMA in tetrahydrofuran (THF) solution are as follows: figure 1 and 2 shown. The maximum absorption wavelengths of the two products in THF solution are both at 415nm, but the emission wavelengths are at 473 and 555nm, respectively, and the Stokes shifts are 58 and 140nm, mainly because POABP-DMA has a larger ground state and excited state It is caused by poor inter-dipole moment and better intramolecular charge transfer (ICT) effect. The absorption bands of the two ...
Embodiment 3
[0113] Example 3: Application of the product in specific labeling of lipid droplets
[0114] (1) Cell culture
[0115] Human cervical cancer cells (HeLa) were provided by Type Culture Collection, USA. HeLa cells were cultured in modified medium (MEM) medium containing 10% heat-inactivated fetal bovine serum (FBS), 100 U / mL penicillin and 100 μg / mL streptomycin (Thermo Scientific), and incubated at 37°C. Contains 5% CO 2 kept in a humidified incubator. Cells were pre-cultured to confluence prior to experimentation. HeLa cells were grown on coverslips in MEM medium supplemented with 10% FBS, penicillin and streptomycin.
[0116] (2) Fluorescent probe staining and cell imaging
[0117] The cells were washed once with phosphate-buffered saline (PBS), and the cells were cultured in MEM medium with 1-20 μM organoboron fluorescent probes for another 30 minutes. Then, the fluorescently labeled cells were mounted on standard mounting media, and were detected by confocal Laser sca...
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