A two-photon fluorescent probe, preparation method and application in formaldehyde detection
A two-photon fluorescence and fluorescent probe technology, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of low detection sensitivity and long response time, and achieve high sensitivity, fast response, and penetration powerful effect
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Embodiment 1
[0047] In this embodiment, a preparation scheme of a two-photon fluorescent probe is provided:
[0048] (1) Dissolve hydroxytetraphenylethylene (348mg) and N-Boc-bromoethylamine (344μL) in acetonitrile (10mL), add potassium carbonate (276mg) and 18-crown-6 (264mg), and heat to reflux 12h, spin dry, separate with chromatographic column, eluent ratio is V 二氯甲烷:V 石油醚 =1:1, spin-dried to obtain compound 1.
[0049] (2) Compound 1 (200mg) was dissolved in dichloromethane (5mL), and trifluoroacetic acid (1.5mL) was added dropwise under stirring, and the reaction progress was followed by TLC spotting. The reaction was completed in about 2 hours, and then directly spin-dried Compound 2 is obtained;
[0050] (3) Dissolve compound 2 (100mg), S-methylisothiosemicarbazide hydroiodide (120mg) in absolute ethanol (5mL), and add triethylamine (72μL), then reflux at 80°C for 4h, spin dry, and the residue was purified by column chromatography with an eluent ratio of V 二氯甲烷 :V 甲醇 =5:1. T...
Embodiment 2
[0052] In this embodiment, a preparation scheme of another two-photon fluorescent probe is provided:
[0053] (1) Dissolve hydroxytetraphenylethylene (174mg) and N-Boc-bromoethylamine (172μL) in acetonitrile (5mL), add potassium carbonate (138mg) and 18-crown-6 (132mg), and heat to reflux 12h, spin dry, separate with chromatographic column, eluent ratio is V 二氯甲烷 :V 石油醚 =5:1, spin-dried to obtain compound 1.
[0054] (2) Compound 1 (100 mg) was dissolved in dichloromethane (2.5 mL), and trifluoroacetic acid (0.75 mL) was added dropwise under stirring, and the reaction progress was tracked by TLC spotting, and the reaction was completed in about 2 hours. Then spin dry directly to obtain compound 2;
[0055] (3) Dissolve compound 2 (50 mg), S-methylisothiosemicarbazide hydroiodide (60 mg) in absolute ethanol (2.5 mL), and add triethylamine (36 μL), then reflux at 80 ° C for 4 h, Spin dry, the residue is purified by chromatographic column, the eluent ratio is V 二氯甲烷 :V 甲醇 =...
Embodiment 3
[0056] Example 3 Structural characterization and performance testing of two-photon fluorescent probes
[0057] 1. NMR and MS characterization of intermediates and probes
[0058] Compound 1: 1 H NMR (400MHz, CDCl 3 ):δ7.14-7.05(m,9H),7.05-6.98(m,6H),6.93(d,J=8.8Hz,2H),6.62(d,J=8.8Hz,2H),4.96(br s ,1H),3.93(t,J=5.0Hz,2H),3.52-3.44(m,2H),1.45(s,9H)ppm. 13 C NMR (100MHz, CDCl 3 ):δ157.03,155.85,143.96,143.91,143.90,140.37,140.23,136.54,132.59,131.35,131.33,131.31,127.73,127.61,127.59,126.37,126.29,126.25,113.53,77.22,66.96,29.71,28.40ppm.HRMS (ESI): calculated for C 33 h 33 NO 3 Na + (M+Na) + 514.2353,found 514.2354.
[0059] Compound 2: HRMS (ESI): calculated for C 28 h 26 NO + (M+H) + 392.2009, found 392.1989.
[0060] Probe TPE-AM: 1 H NMR (400MHz, DMSO-d 6 ):δ7.19-7.07(m,9H),7.01-6.92(m,6H),6.87(dd,J=8.8,3.5Hz,2H),6.71(dd,J=8.8,3.5Hz,2H), 4.74(br s,1H),3.97(t,J=5.0Hz,1H),3.92(t,J=5.4Hz,1H),3.51(br s,1H),2.96(t,J=5.4Hz,1H ) ppm. 13 C NMR (100MHz, CDCl 3 ):...
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