Near-infrared fluorescent probe for detecting temperature as well as preparation method and application of near-infrared fluorescent probe
A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve the problems of temperature detection limit, temperature staying outside the body, etc., and achieve the effects of high sensitivity, large Stokes shift, and low background interference
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Embodiment 1
[0042] Example 1: Preparation of compound (2)
[0043]Para-diethylaminoacetophenone (0.38 g, 2.0 mmol) and malononitrile (0.40 g, 6.0 mmol) were completely dissolved in a round bottom flask containing 20 mL of toluene. Then, ammonium acetate (0.70 g, 0.4 mmol) and acetic acid (0.14 g, 2.2 mmol) were added to the reaction system, and the mixture was refluxed at 110° C. for 18 hours. After cooling the reaction system to room temperature, the solid was collected by filtration. Purified by silica gel column chromatography eluted with petroleum ether / ethyl acetate (5:1 v / v), the eluate containing the target compound was collected, and concentrated under reduced pressure to obtain 454.67 mg of pure compound (2) as a pale yellow solid, The product yield was 95%. 1 H NMR (500MHz, Chloroform-d) δ 7.71(s, 1H), 7.69(s, 1H), 6.69(s, 1H), 6.67(s, 1H), 3.45(t, J=7.1Hz, 4H) , 2.58(s, 3H), 1.23(t, J=7.1Hz, 6H). See H NMR Figure 17 .
Embodiment 2
[0044] Example 2: Preparation of compound (1)
[0045] Compound (3) (0.07g, 0.42mmol), compound (2) (0.13g, 0.42mmol) and piperidine (0.0072g, 0.084mmol) were added to 4ml of ethanol, stirred at 80°C for reflux reaction for 2h, and the progress was detected by TLC , the reaction solution was extracted with dichloromethane, the collected organic phase was concentrated under reduced pressure, subjected to silica gel column chromatography, and a mixed solvent with a volume ratio of dichloromethane and petroleum ether of 1:1 was used as the eluent, and the eluate containing the target product was collected. The solution was concentrated under reduced pressure to obtain 40.84 mg of pure compound (1), which was an orange-red solid, and the reaction yield was 25%. 1H NMR(500MHz, Chloroform-d)δ7.46-7.43(m,2H),7.37-7.33(m,2H),7.30(d,J=15.2Hz,1H),7.01(d,J=15.2Hz, 1H), 6.73–6.70 (m, 2H), 6.65 (d, J=9.0Hz, 2H), 3.44 (tt, J=7.1, 3.6Hz, 8H), 1.23 (dt, J=11.5, 7.1Hz, 12H) ).13C NMR (126MHz...
Embodiment 3
[0046] Example 3: Fluorescence absorption spectrum of compound (1) (5 μM) in PBS detection system (excitation wavelength 530 nm, emission wavelength 660 nm.)
[0047] A certain amount of compound (1) of Example 2 was weighed and prepared into a probe stock solution with a concentration of 1 mM in dimethyl sulfoxide, and 2 μL of the stock solution was extracted and added to 398 μL of PBS buffer. It was transferred to a 96-well plate, and the fluorescence absorption spectrum and emission spectrum of compound (1) were measured.
[0048] Fluorescence spectrum see image 3 and Figure 4 .
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