Polyamine containing triazole ring and preparation method and application thereof

[0046] Example 1

[0047] (1) Synthesis of 1,4-diazide methylbenzene

[0048] Add p-dichloromethylbenzene (0.05mol) and NaN in a three-necked flask 3 (0.15mol), toluene (20mL), and N,N-dimethylformamide (20mL), heated to 70~75℃ with stirring, reacted at constant temperature for 3 hours, after the reaction, the reaction product was cooled to room temperature and poured into In 200 mL of deionized water, stand overnight under freezing conditions to precipitate white flake crystals, filtered, and the filter cake was washed with deionized water, and dried to obtain a white powdery solid with a yield of 90%. Melting point: 27~29℃; FT-IR (KBr, v, cm -1 ): 2089(-N 3 Stretching vibration); 1 H-NMR(CDCl 3 , TMS) δ: 7.33 (s, 4H, Ha), 4.35 (s, 4H, Hb), its structural formula is:

[0049]

[0050] (2) Synthesis of 1,4-bis[4-(3-aminophenyl)-1,2,3-triazole-1-methylene]benzene

[0051] Add 1,4-diazide methylbenzene (0.01mol), m-aminophenylacetylene (0.02mol), CuSO to the flask 4 ·5H 2 O (0.005mol), so

[0053] Example 2

[0054] (1) Synthesis of 4,4-diazide methyl biphenyl

[0055] Add p-dichloromethyl biphenyl (0.05mol) and NaN in a three-necked flask 3 (0.15mol), toluene (20mL) and DMF (20mL), heated to 70~75℃ under stirring, reacted at constant temperature for 3 hours, after the reaction, the reaction product was cooled to room temperature, poured into 200mL deionized water, and left to stand overnight , A white solid precipitated, filtered, the filter cake was washed with deionized water, and dried to obtain a white powder solid with a yield of 89%. Melting point 68~71℃; FT-IR(KBr, v, cm -1 ): 2089(-N 3 Stretching vibration); 1 H-NMR(CDCl 3 , TMS) δ: 7.33 (s, 4H, Ha), 7.29 (s, 4H, Ha), 4.35 (s, 4H, Hb), its structural formula is:

[0056]

[0057] (2) Synthesis of 4,4-bis[4-(3-aminophenyl)-1,2,3-triazole-1-methylene]biphenyl

[0058] Add 1,4-diazide methylbenzene (0.01mol), m-aminophenylacetylene (0.02mol), CuSO to the flask 4 ·5H 2 O (0.005 mol), sodium ascorbate (0.01 mol), triet

[0060] Example 3

[0061] (1) Synthesis of diethylene glycol diazide

[0062] The synthesis reaction is carried out in two steps, firstly the chlorination of polyethylene glycol, and then azide, the reaction equation is:

[0063]

[0064] Add 0.08mol of polyethylene glycol, SOCl into a 500mL flask equipped with stirring 2 200mL, equipped with spherical condenser and gas absorption tube, heated to 65℃ with oil bath, and stirred for 72h. After the reaction, the excess SOCl was removed by vacuum distillation on the rotary evaporator 2 , Join NaHCO 3 The aqueous solution is filtered to pH>7. 50mL CHCl for filtrate 3 Extract three times, then add anhydrous magnesium sulfate to dry, filter with suction, and distill off the solvent to obtain polyethylene glycol chlorinated product.

[0065] Add 0.08mol of the chlorinated product of the above-synthesized polyethylene glycol into a 250mL single-necked round bottom flask equipped with stirring, NaN 3 0.4mol, 150mL deionized water, install a spher