Triarylmethane compound and its preparation method and use

[0057] Synthesis of Triarylmethane Compound 3

[0058]

[0059] (1) Synthesis of trithienyl methane 1:

[0060] 1.12g of 2-thiophenecarbaldehyde, 20mL thiophene, 2gNaHSO 4 ·SiO2 2 Place in a three-necked flask, stir and reflux at 85°C; after 6h, cool to room temperature. The reactant was suction-filtered, washed with dichloromethane, and the solvent was spin-dried; petroleum ether was used as eluent, and 200-300 mesh silica gel chromatography was used to purify and separate the pure product as a white solid with a yield of 41%. Melting point: 51-53°C.

[0061] (2) Synthesis of trithiophene methane formaldehyde 2:

[0062] Under argon protection, under ice-water bath, 2.45g POCl 3 Add dropwise to 1.17g of DMF in 1,2-dichloroethane solution, stir, and continue to react for 1h; add compound 1 (1.04g) dissolved in 1,2-dichloroethane, stir at room temperature for 2h, heat up to reflux 12h; cooled to room temperature, poured into crushed ice, added sodium acetate solution (...

[0066] Synthesis of Triarylmethane Compound 6

[0067]

[0068] (1) Synthesis of bromotrithienyl methane 4:

[0069] Place 0.5 g of compound 1 in DMF in a -5°C ice-water bath, add 0.338 g of NBS in DMF dropwise, stir for 20 min, and stir at room temperature for 2 h; then pour the crude product into ice water and extract with ethyl acetate. The organic phases were combined, dried, and the solvent was rotary evaporated under reduced pressure to obtain a pink oily substance through column chromatography (petroleum ether) with a yield of 45%; 1 HNMR (CDCl 3 )δ (ppm): 6.03 (s, 1H), 6.68 (d, 1H), 6.9 (d, 1H), 6.96-6.97 (m, 4H), 7.25 (d, 2H).

[0070] (2) Synthesis of trithiophene methanethiophene carboxaldehyde 5:

[0071] In a three-neck flask, dissolve 1g of compound 4, 0.45g of 5-formyl-2-thiophene boronic acid in 30mL of toluene, add 5mL of potassium carbonate solution and Pd(PPh3)4 (0.15g), and replace the argon; 90°C Reflux and stir for 10 h; cool and spin dry toluene; ...

[0075] Synthesis of Triarylmethane Compound 10

[0076]

[0077] (1) Synthesis of hexyltrithiophene methanethiophene carboxaldehyde 9:

[0078] The synthesis method is the same as (2) in Example 2, except that the raw materials are replaced; 1 HNMR (CDCl 3 )δ(ppm): 5.91(s,1H), 6.61(d,2H), 6.75(d,2H), 6.89(d,1H), 7.17(d,1H), 7.20(d,1H), 7.63( d, 1H), 9.83 (s, 1H).

[0079] (2) Synthesis of triarylmethane compound 10:

[0080] The synthesis method is the same as (3) in Example 1, except that the raw materials are replaced; 1 HNMR([D6]DMSO)δ(ppm): 6.24(s,1H), 6.68(d,2H), 6.79(d,2H), 6.94(d,1H), 7.31(d,1H), 7.36(d ,1H), 7.63(d,1H), 8.05(s,1H).