MA-11-RhB was synthesized through a two-step method. First, RhB (0.48 g, 1.0 mmol) and EDCI (0.23 g, 1.2 mmol) were dissolved in 30-ml anhydrous DCM under the ice bath and stirred for 10 min. Then, N,N-dimethylethylenediamine (0.50 ml, 4.6 mmol) and DMAP (6.11 mg, 0.05 mmol) were added. The solution was allowed to slowly rise to room temperature and reacted overnight in the dark. After that, the solution was concentrated, and the product was purified by column chromatography.

1H NMR (500 MHz, CDCl3): δ (ppm) 8.28 (d, 1H, Ph), 7.84 (t, 1H, Ph), 7.76 (t, 1H, Ph), 7.34 (d, 1H, Ph), 7.08 (d, 2H, Ph), 6.97 (d, 2H, Ph), 6.84 (s, 2H, Ph), 3.66 (m, 2H CONH─CH2─CH2─N; 8H, CH3CH2─N), 2.55 (t, 2H, CONH─CH2CH2─N), 2.24 (s, 6H, N─CH3), and 1.34 (t, 12H, CH3─CH2─N).

Next, above product (0.27 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 THF to remove the impurities. MA-11-RhB was obtained as a reddish-brown solid with a yield of 38%.

1H NMR (500 MHz, CDCl3): δ (ppm) 8.28 (d, 1H, Ph), 7.82 (t, 1H, Ph), 7.74 (t, 1H, Ph), 7.33 (d, 1H, Ph), 7.07 (d, 2H, Ph), 6.90 (d, 2H, Ph), 6.84 (s, 2H, Ph), 6.09 (s, 1H, CH2═C), 5.54 (s, 1H, CH2═C), 4.13 (t, 2H, ─CH2─OOC), 4.01 (t, 2H, CONH─CH2─CH2─N), 3.72 (t, 2H, CONH─CH2CH2─N), 3.52 (t, 2H, CH2CH2─N), 3.66 (m, 8H, CH3CH2─N), 3.37 (s, 6H, N─CH3), 1.94 (s, 3H, CH3─C═C), 1.76 (m, 2H, ─CH2─CH2─OOC), 1.66 (m, 2H, ─CH2─CH2─N), and 1.10 to 1.40 [m, 12H + 14H, CH3─CH2─N + ─(CH2)7─].

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