MA-11-N3 was synthesized through a two-step method. First, NaN3 (0.67 g, 10 mmol) and 2-dimethylaminoethyl chloride hydrochloride (0.72 g, 5.0 mmol) were dissolved in 25 ml of DI water under nitrogen atmosphere. After reaction at 60°C for 15 hours, NaOH (0.20 g, 5.0 mmol) was added, and the solution was extracted with diethyl ether three times. The organic layer was collected, and the solvent was evaporated off slowly to avoid the loss of product. 2-Azido-N,N-dimethylethanamine was obtained as a light yellow liquid with a yield of 52%.

1H NMR (500 MHz, CDCl3): δ (ppm) 3.39 (t, 2H, ─CH2─N3), 2.54 (t, 2H, ─CH2─N), and 2.31 (6H, CH3─N).

Next, 11-bromoundecyl methacrylate (0.32 g, 1.0 mmol), 2-azido-N,N-dimethylethanamine (0.29 g, 2.5 mmol), and 4-methoxyphenol (trace) were dissolved in 10-ml THF under nitrogen atmosphere. After reaction at 60°C for 15 hours, the solvent was evaporated off, and the obtained crude product was washed with diethyl ether to remove the impurities. MA-11-N3 was obtained as a white solid with a yield of 37%.

1H NMR (500 MHz, CDCl3): δ (ppm) 6.09 (s, 1H, CH2═C), 5.56 (s, 1H, CH2═C), 4.13 (t, 2H, ─CH2─OOC), 3.70 (t, 2H, N─CH2─CH2─N3), 3.54 (t, 2H, N─CH2─), 3.42 (t, 2H, N─CH2CH2─N3), 3.38 (s, 6H, N─CH3), 1.94 (s, 3H, CH3─C=C), 1.76 (m, 2H, ─CH2─CH2─OOC), 1.67 (m, 2H, ─CH2─CH2─N), and 1.24 to 1.44 [m, 14H, ─(CH2)7─]. MALDI-TOF (positive ion): Calcd m/z for C19H37O2N4+: 353.29; found, 353.31.

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