General procedure for the synthesis of 3-bromo perylene from perylene:
1. 3.0 g (11 mmol) of perylene was dissolved in 700 mL of dichloromethane and stirred for 5 minutes until completely dissolved.
2. 2.11 g (12 mmol, 1.1 eq.) of N-bromosuccinimide was slowly added dropwise to the above solution at room temperature.
3. After the dropwise addition, the reaction mixture was stirred at room temperature overnight. 4.
4. Upon completion of the reaction, the reaction solution was purified by silica gel column chromatography with the unfolding reagent ratio of dichloromethane:hexane=1:1 (v/v) to remove unreacted N-bromosuccinimide.
5. Collect the target component and concentrate the solvent under reduced pressure to obtain yellow crystalline 3-bromhydrazone in 90% yield.
6. The structure of the product was confirmed by 1H-NMR and ESI-MS.
- 1H-NMR (CDCl3, 400MHz) δ: 7.46-7.51 (m, 2H), 7.59 (t, J=4.4Hz, 1H), 7.68-7.72 (m, 2H), 7.78-7.80 (m, 1H), 7.98-8.04 (m, 1H), 8.09-8.14 (m, 1H), 8.17- 8.28 (m, 3H). 8.28 (m, 3H).
- ESI-MS (C20H11Br): Calculated: 330.00; measured: 331.9 [M+H]+.
