Rhodamine fluorochrome and preparation method and application of rhodamine fluorochrome
A technology of fluorescent dyes and general formulas, applied in the direction of azo dyes, organic dyes, luminescent materials, etc., can solve the problems of non-reversibility, inability to achieve reversible cycle detection, fast response and unsatisfactory fast response, etc., to achieve good reversibility, Responsive, high-sensitivity effects
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[0061] The present invention further provides a method for preparing the above-mentioned rhodamine fluorescent dye, which is characterized by comprising the following steps (1) and (2).
[0062] Step (1): Add the rhodamine-based fluorescent dye represented by general formula III into the alcohol solvent, stir at room temperature, so that the rhodamine-based fluorescent dye is evenly dispersed in the alcohol solvent, and then dropwise add the rhodamine-based fluorescent dye Stoichiometrically excess diethylenetriamine or triethylenetetramine, after the dropwise addition, heat to reflux the solvent and react until the reaction solution becomes clear, then cool to room temperature, evaporate the solvent, and dissolve the residue in dichloromethane , add a small amount of water to wash or add a small amount of water to the residue, extract with dichloromethane, then dry over anhydrous sodium sulfate, filter, and after vacuum drying, separate and purify the residue to obtain an inte...
Embodiment 1
[0099] Embodiment 1: the synthesis of fluorescent probe compound SRR
[0100]
[0101] (1) Synthesis of intermediate RR
[0102] In a 250 ml one-necked flask, Rhodamine B (9.8 g, 20.42 mmol) was dissolved in 150 ml ethanol. Under vigorous stirring, 15ml of pure triethylenetetramine (excessive amount) was added dropwise, and the reaction was refluxed under nitrogen protection for 24h. The color of the solution changed from pink to colorless, cooled to room temperature, evaporated the solvent under reduced pressure, added a small amount of water, then extracted with dichloromethane, anhydrous NaSO 4 After drying, filtering, and vacuum drying, silica gel column chromatography, the eluent was dichloromethane / methanol (v / v, 300:1), and 1.456 g of the target product was obtained by column separation. 1 HNMR (400MHz, CDCl 3 ,25°C,TMS),δ:7.73(d,J=7.4Hz,2H),7.51–7.27(m,2H),7.26(m,4H),7.08(d,J=7.5Hz,4H), 6.47–6.25(m,8H),3.34(m,J=14.1,7.0Hz,20H),2.85(t,J=14.1,7.0Hz,4H),1.28(t,J=15...
Embodiment 2
[0105] Embodiment 2: the synthesis of fluorescent probe compound SR
[0106]
[0107] (1) Synthesis of intermediate R
[0108] In a 250ml one-necked flask, Rhodamine 6G (9.8g, 20.42mmol) was dissolved in 150ml of hot ethanol. Under vigorous stirring, 6.7ml of pure diethylenetriamine (excessive amount) was added dropwise, and the reaction was refluxed under nitrogen protection for 24h. The color of the solution changed from pink to colorless, cooled to room temperature, evaporated the solvent under reduced pressure, added a small amount of water, then extracted with dichloromethane, anhydrous NaSO 4 After drying, filtering, and vacuum drying, silica gel column chromatography, the eluent was dichloromethane / methanol (v / v, 15:1), and R (2.488g, yield: 24.9%) was obtained by column separation. 1 H NMR (400MHz, CDCl 3 ,25°C,TMS),δ:7.90(t,1H),7.43(t,2H),7.01(t,1H),6.32(s,2H),6.22(s,2H),3.52(t,2H ),3.20(t,4H),2.54(t,2H),2.31(m,4H),1.85(s,6H),1.36(t,6H)ppm; 13 C NMR (100MHz, C...
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