High brightness, high stability fluorescent dyes and its synthesis and application of activated ester
A technology containing active esters and fluorescent dyes, used in luminescent materials, organic dyes, azo dyes, etc., can solve the problems of reduced quantum yield, difficult to penetrate cell membranes, affecting molecular labeling performance, stability, compatibility, etc. , to achieve the effect of low-cost synthetic raw materials, simple and general methods, and stable fluorescent labeling
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Embodiment 1
[0040] Synthesis of NHSM-DAze
[0041] Synthesis of Intermediate 2-(N-(4-Bromo-5-nitro-1,8-naphthalimide))ethylaminoacetate (COMe-NBr)
[0042]
[0043] 4-Bromo-5-nitro-1,8-naphthalimide (1.00 g, 3.11 mmol) was dissolved in 80 mL of ethanol, to which was added glycine ethyl ester hydrochloride (1000 mg, 7.17 mmol) and 1.00 g of trisulfite Ethylamine. After reacting at 90° C. for 24 hours, the solvent was distilled off under reduced pressure, and the residue was separated by silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 962 mg of white solid with a yield of 76%. Its nuclear magnetic spectrum data are as follows:
[0044] 1 H NMR (400MHz, CDCl 3 )δ8.73(d,J=7.8Hz,1H),8.53(d,J=7.9Hz,1H), 8.24(d,J=7.9Hz,1H),7.94(d,J=7.8Hz,1H) ,4.92(s,2H),4.26(q,J=7.1Hz,2H),1.31(t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3)δ167.36, 162.48, 161.75, 151.56, 136.06, 132.66, 131.64, 130.74, 125.26, 124.71, 123.60, 122.00, 121.35, 61.94, 41.64, 14.16.
[0045] Its high-reso...
Embodiment 2
[0065] Synthesis of NHSM-DAC
[0066] Synthesis of Intermediate 2-(N-(4-Bromo-5-nitro-1,8-naphthalimide))ethylaminoacetate (COMe-NBr)
[0067]
[0068] 4-Bromo-5-nitro-1,8-naphthalimide (1.00 g, 3.11 mmol) was dissolved in 20 mL of ethanol, and glycine ethyl ester hydrochloride (3000 mg, 21.5 mmol) and 3.00 g of trisamine were added thereto. Ethylamine. After reacting at 40° C. for 1 h, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 418 mg of a white solid with a yield of 33%.
[0069] Synthesis of Intermediate COOH-DAC
[0070]
[0071] (1) Synthesis of COMe-DAC
[0072] COMe-NBr (200 mg, 0.49 mmol) was dissolved in 20 mL of ethylene glycol methyl ether, and 400 mg of 1,2-cyclohexanediamine was added thereto. The reaction solution was slowly heated to 100 °C and reacted for 12 h. Ethylene glycol methyl ether was removed under reduced pressure, and t...
Embodiment 3
[0088] Synthesis of NHSB-DAC
[0089] Synthesis of the intermediate 6-(N-(4-bromo-5-nitro-1,8-naphthalimide))aminobutyric acid ethyl ester (BCOMe-NBr)
[0090]
[0091] 4-Bromo-5-nitro-1,8-naphthalimide (1.00 g, 3.11 mmol) was dissolved in 80 mL of ethanol, and thereto was added ethyl 4-aminobutyrate hydrochloride (1.00 g, 6.21 mmol) ) and 3.00 g of triethylamine. After reacting at 80°C for 10 h, the solvent was distilled off under reduced pressure, and the residue was separated by silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 608 mg of white solid with a yield of 45%. Its nuclear magnetic spectrum hydrogen spectrum and carbon spectrum data are as follows:
[0092] 1 H NMR (400MHz, CDCl 3 )δ8.71(d,J=7.8Hz,1H),8.52(d,J=7.9Hz,1H), 8.22(d,J=7.9Hz,1H),7.93(d,J=7.8Hz,1H) ,4.25(t,J=7.1Hz,2H),4.10(q,J=7.1Hz,2H),2.44(t,J=7.4Hz,2H),2.09(p,J=7.3Hz,2H),1.24 (t,J=7.1Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ172.72,162.85,162.09,151.33,136.00,132.40, 131.30,13...
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