Degradable cationic surfactants and use thereof in enhancing chemiluminescence
A surfactant, chemiluminescence technology, applied in chemiluminescence/bioluminescence, biochemical equipment and methods, and analysis by chemical reactions of materials, etc., can solve problems such as less biodegradation, aquatic biological environmental risks, etc.
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Embodiment 1
[0087] Example 1: Synthesis of Cationic Amide Surfactant 1 ( image 3 )
[0088] Compound II
[0089] Palmitic acid (i, 2.564 g, 10.00 mmol), toluene (100 mL) and N,N-dimethylethylenediamine (1.147 mL, 10.50 mmol) were mixed and refluxed for 20 hours. The reaction mixture was concentrated to dryness to obtain 3.21 g of a pale yellow solid. The crude solid was recrystallized from dry acetone (75 mL). The desired product ii (1.83 g) was obtained in the form of white needle crystals. 1 H-NMR (500MHz, CDCl 3 ),0.87(t,3H, J =6.5),1.20-1.35(m,24H),1.55-1.70(m,2H),2.17(t,2H, J =7.5),2.30(s,6H),2.49(t,2H, J =5.5),3.36(dt,2H, J =5.5,5.5),6.25(brs,1H). MALDI-TOFMS m / z 327.4(M+H + ); HRMS m / z 327.3376 (M+H + ) (computed to be 327.3375).
[0090] Compound III
[0091] Compound ii (1.41 g, 4.32 mmol), acetone (50 ml) and iodomethane (0.309 ml, 4.97 mmol) were refluxed at 80°C for 6 hours under an argon atmosphere. The reaction mixture was cooled to room temperature,...
Embodiment 2
[0094] Example 2: Synthesis of Cationic Carbonate Surfactant 2 ( Figure 4 )
[0095] compound v
[0096] A mixture of dodecanol (iv, 2.236 mL, 10.00 mmol), triethylamine (1.394 mL, 10.00 mmol) and diphenyl carbonate (2.142 g, 10.00 mmol) was heated to 80 °C for 16 h . Then, 3-dimethylamino-1-propanol (2.366 mL, 20.00 mmol) was added and heated to 80°C for a further 16 hours. The reaction mixture was then concentrated under reduced pressure to obtain 3.92 g of a dark yellow oil. It was purified by silica gel column chromatography using methanol / ethyl acetate as eluent (1:9). The desired product v (2.63 g) was obtained as a yellow oil. 1 H-NMR (500MHz, CDCl 3 )0.88(t,3H, J =6.5),1.20-1.42(m,18H),1.61-1.71(m,2H),1.87-1.98(m,2H),2.33(s,6H),2.49(brt,2H, J =7.0),4.12(t,2H, J =6.5),4.19(t,2H, J=6.3). MALDI-TOFMS m / z 316.3(M+H + ); HRMS m / z 316.2855 (M+H + ) (computed to be 316.2852).
[0097] compound vi
[0098] Compound v (1.500 g, 4.75 mmol), acetone (50 ...
Embodiment 3
[0101] Example 3: Chemiluminescence measurement
[0102] To investigate the effect of degradable cationic surfactants on the chemiluminescence of acridinium esters, two exemplary cationic surfactants containing cleavable bonds ( figure 2 A). The critical micelle concentrations (CMC) of the two surfactants are shown in figure 2 In A. The synthetic scheme for described two surfactants is shown in Figure 3-4 and described in Example 1 and Example 2 above. Both surfactants were dissolved in Reagent 1 (0.1 M nitric acid with 0.5% hydrogen peroxide) at a concentration five times their reported CMC in water. CTAC dissolved in Reagent 2 (0.25 M NaOH) was used as a control surfactant. The two kinds of carbonate cationic surfactants and amide cationic surfactants ( figure 2 A) dissolved in Reagent 1 for stability, especially during long-term storage (Stjerndahl and Holmberg, J. Colloid and Interface Sci ., 2005, 291, 570-576). Three acridinium esters ( figure 2 B, compo...
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