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Amino-substituted azafluoroboron dipyrrole near-infrared pH fluorescent probe and its preparation method and application
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A fluoroborate dipyrrole and near-infrared technology, applied in the field of near-infrared absorption pH fluorescent probes, to achieve high selectivity and enhanced fluorescence emission
Inactive Publication Date: 2020-05-05
PINGDINGSHAN UNIVERSITY
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At present, there are few reports on fluorescent probes in the low pH range (pH<4).
Method used
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Embodiment 1
[0026] Embodiment 1. Synthesis of compound 1a:
[0027] In a 100mL round bottom flask, add 10mmol 4-N,N-diethylamino-acetophenone and 10mmol benzaldehyde in 10mL ethanolsolvent, slowly add (10mL) 10% NaOH aqueous solution dropwise, the reaction is over for 5 hours, and the pressure is reduced Suction filtration, washing with water until neutral, washing with a small amount of cold ethanol, and drying to obtain yellow product 1a.1a: 1 H NMR (500MHz, CDCl 3 ,δ):7.98(d,J=7.5Hz,2H,),7.70(d,J=13Hz,2H,),7.48-7.58(m,5H,Ar H),6.68(d,J=5.5Hz, 2H,), 3.44 (q, J=6Hz, 4H, CH 2 ), 1.22(t, J=6Hz, 6H, CH 3 ).ESI-MS(m / z):[M+Na] + calcd for C 19 h 21 NONa302.16; Found, 302.58.
Embodiment 2
[0028] The synthesis of embodiment 2. compound 2a:
[0029] Take (4mmol) 1a in a 50mL round bottom flask, 20mmol nitromethane and 20mmol diethylamine, 30mL methanolsolvent, reflux at 60°C for 12 hours, after the reaction, the reaction mixture was extracted with distilled water and ethyl acetate, and then extracted with anhydroussodiumsulfate The organic layer was dried, the solvent was removed by rotary evaporation under reduced pressure, and the product 2a was obtained by drying. 2a: 1 H NMR (500MHz, CDCl 3 ,δ):7.79(d,J=9.0Hz,2H,Ar H),7.44(d,J=8.5Hz,2H,Ar H),7.17(d,J=8.5Hz,2H,Ar H),6.58 (d,J=9.0Hz,2H,Ar H),4.81-4.85(m,1H,CH),4.62-4.66(m,1H,CH),4.10-4.21(m,1H,CH),3.42(q ,J=7.0Hz,4H,CH 2 ), 1.20(t, J=6Hz, 6H, CH 3 ).ESI-MS(m / z):[M+Na] + calcdforC 20 h 24 N 2 o 3 Na, 363.17; Found, 363.51.
Embodiment 3
[0030] Embodiment 3. Synthesis of compound 3a:
[0031] Take (3mmol) 2a in a 50mL two-neck round-bottom flask, add (75mmol) ammonium acetate, heat and reflux in 30mL n-butanol under nitrogen protection for 24h, cool to room temperature after the reaction is complete, filter, wash with cold ethanol, and dry to obtain dark blue Coloredsolid 3a.3a: 1 H NMR (500MHz, CDCl 3 ,δ):7.92(d,J=8.5Hz,4H,Ar H),7.79(d,J=8.5Hz,4H,ArH),7.52(d,J=8.0Hz,4H,Ar H),7.07( d,J=8.0Hz,4H,Ar H),6.78(d,J=8.5Hz,4H,ArH),3.48(q,J=7.0Hz,8H,CH 2 ), 1.26(t, J=7.0Hz, 12H, CH 3 ).MALDI-TOF(m / z):calcd for C 40 h 41 N 5 ,591.79; Found, 591.71.
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Abstract
The invention discloses an amino-substituted BF2-chelated azadipyrromethene (aza-BODIPY) near-infrared compound. The compound has a structure shown in the description. Compared with the prior art, theamino-substituted BF2-chelated azadipyrromethene near-infrared compound has the following obvious advantages: the p-N,N-diethyl-substituted BF2-chelated azadipyrromethene near-infrared compound is synthesized for the first time, introduction of an amino group can make the absorption spectrum of BF2-chelated azadipyrromethene generate a significant red shift, and therefore application in biological aspects is facilitated. After the photosensitizer is protonated by hydrogen ions, the ultraviolet absorption spectrum changes significantly, the color of the solution is changed from purple to blue,meanwhile a photoinduced process is selectively reduced, and the fluorescence emission is reinforced, therefore the compound NEt2-aza-BODIPY has an application of high-selectivity naked-eye color recognition on hydrogen ions and fluorescent recognition. The invention discloses a preparation method of the amino-substituted BF2-chelated azadipyrromethene near-infrared compound.
Description
technical field [0001] The invention relates to a near-infrared absorbing pH fluorescence probe, in particular to an amino-substituted azafluoroboron dipyrrole (aza-BODIPY) near-infrared absorbing material and its preparation method and use. Background technique [0002] In environmental analysis, chemical reactionprocess control, biomedicine, etc., pH is an important parameter, and the measurement of pH value is of great significance. At present, the pH measurement methods mainly include indicator method, glass electrode method, optical sensor method and so on. Compared with other pH measurement methods, pH probe measurement methods based on optical signal changes have attracted widespread attention due to their advantages of high sensitivity, good selectivity, and short reaction time. At present, some pH fluorescent probes have been reported, but most pH fluorescent molecular probes have a wide detection range, which reduces the sensitivity of the probes. At present, th...
Claims
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