A kind of azine hydrazine compound and its preparation method and application
A technology of compound and hydrazine, which is applied in the field of azine hydrazine compounds and their preparation, can solve problems such as difficult detection and fluorescence analysis, high non-radiative transition ratio, and decrease in fluorescence quantum yield, so as to achieve good solubility, Effect of increasing Stokes shift and enhancing AIE performance
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Embodiment 1
[0055] According to the following synthetic route, the following compounds are specifically synthesized:
[0056]
[0057] (1) Synthesis of compound 2
[0058] A mixture of compound 1 (1.1 g, 2 mmol) and excess hydrazine hydrate was stirred under reflux for 4 hours. After the reaction was completed, the solvent and the remaining hydrazine hydrate were removed by rotary evaporation to obtain compound 2 as a transparent oil with a yield of 100% (1.2 g).
[0059] (2) Synthesis of compound M1-DPAN
[0060] Compound 2 (0.57 g, 1 mmol) and compound 3 (0.258 g, 1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated with a chromatographic silica gel column, and the eluent used was methanol: acetone: dichloromethane = 1:16:30 to obtain a yellow solid compound M1-DPAN with a yield of 20.8% (0.13g).
[0061] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):12.68(s,1H),8.88(s,1H),8.28(d, J=8.3Hz,1H),7.73(d,J=8.1Hz,1H),7.71–7.66 (m,2H),7.53–7.50(m...
Embodiment 2
[0065] Example 2: Compounds in Example 1 are used for fluorescent staining of Gram-positive bacteria
[0066] (1) Bacterial culture
[0067] a. A single colony of Staphylococcus aureus (Gram-positive) was inoculated in 5 mL of NB medium, and cultured at 37° C. for 12 hours. Afterwards, the colony was centrifuged at 7100 rpm for 1 minute, while washing with phosphate buffered saline (PBS, 10 mM, pH=7.4) three times, the supernatant was discarded, and the remaining Staphylococcus aureus was suspended in PBS, and then incubated at 600 nm Dilute to 1.0 optical density (OD 600 = 1.0). Bacillus subtilis (Gram-positive), Enterococcus faecalis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), Escherichia coli (Gram-negative), S. Yeast (fungus) and Candida albicans (fungus).
[0068] b. Mixed strains (Saccharomyces cerevisiae, Bacillus subtilis and Pseudomonas aeruginosa) were co-stained with M1-DPAN at a concentration of 5 μM in PBS buffer solution for 20 minutes at 37°C, a...
Embodiment 3
[0080] According to the following synthetic route, the following compounds are specifically synthesized:
[0081]
[0082] (1) Synthesis of compound M2-DPAN
[0083] Compound 2 (0.57 g, 1 mmol) and compound 4 (0.258 g, 1.5 mmol) were stirred under reflux for 4 hours. After the reaction was completed, it was separated by a chromatographic silica gel column, and the eluent used was methanol:dichloromethane=1:15 to obtain a yellow solid compound M2-DPAN with a yield of 15.3% (0.096g).
[0084] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm): 13.08(s,1H), 9.72(s,1H), 8.18(d, J=8.5Hz, 1H), 7.76(t, J=8.1Hz, 2H), 7.73–7.68 (m,2H),7.57–7.51(m,1H), 7.38–7.33(m,1H),7.32–7.28(m,2H),7.09(d,J=9.0Hz,1H),7.03–6.99(m ,2H), 6.94–6.88(m,2H),4.06–3.98(m,4H),3.74(dd,J=9.1,4.5Hz,8H),2.47(br,8H), 2.42–2.30(m,4H ),1.89–1.75(m,5H),1.63–1.47(m,8H),1.46–1.35(m,4H).
[0085] 13 C NMR (125MHz, CDCl 3 ),δ(TMS,ppm):167.32,161.38,160.98,159.78, 159.62,134.01,132.71,130.90,130.69,130.32,129.06,128.00,127.68...
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