MA-12-Pyr was synthesized through a two-step method. 1-Pyrenecarboxylic acid (0.50 g, 2.0 mmol) and EDCI (0.46 g, 2.4 mmol) were dissolved in 40-ml anhydrous DCM under the ice bath and stirred for 10 min. N,N-Dimethylethylenediamine (1.0 ml, 9.2 mmol) and DMAP (12.2 mg, 0.1 mmol) were added. The solution was allowed to slowly rise to room temperature and reacted 24 hours in the dark. After that, the solution was concentrated, and the product was purified by column chromatography.

1H NMR (500 MHz, CDCl3): δ (ppm) 9.27 (s, 1H, Ph), 8.67 (s, 1H, Ph), 8.30 to 8.05 (m, 7H, Ph), 3.64 (t, 2H, CONH─CH2─CH2─N), 2.50 (t, 2H, CONH─CH2CH2─N), and 2.28 (s, 6H, N─CH3).

Next, above product (0.16 g, 0.50 mmol), 11-bromoundecyl methacrylate (0.16 g, 0.50 mmol) and 4-methoxyphenol (trace) were dissolved in 10-ml acetonitrile under nitrogen atmosphere. After reaction at 60°C for 24 hours in the dark, the solvent was evaporated off, and the crude product was washed with diethyl ether to remove the impurities. MA-11-Pyr was obtained as a pea green solid with a yield of 57%.

1H NMR (500 MHz, CDCl3): δ (ppm) 9.26 (s, 1H, Ph), 8.66 (s, 1H, Ph), 8.31 to 8.01 (m, 7H, Ph), 6.09 (s, 1H, CH2═C), 5.55 (s, 1H, CH2═C), 4.50 (t, 2H, N─CH2─CH2─NHOC), 4.15 (t, 2H, ─CH2─OOC), 3.75 (t, 2H N─CH2─CH2─NHOC), 3.54 (t, 2H, CH2CH2─N), 3.37 (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 1.24-1.44 (m,14H, ─(CH2)7─). MALDI-TOF (positive ion): Calcd m/z for C36H47O3N2+: 555.36; found, 555.47.

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