Regular polymer containing monofluorine-substituted benzo-hetero[1,3]diazole and preparation and application of regular polymer
A technology of benzoheteropolymers, applied in the field of organic photoelectric materials, to achieve the effect of good crystal arrangement, easy purification and simple synthesis route
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Embodiment 1
[0051] The chemical process formula in Example 1 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:
[0052]
[0053] (1) Compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole) is disclosed in the literature [Adv.Mater.2012,24,3646-3649] Prepared by the method, the specific steps are: dissolving 4-fluorobenzene-1,2-diamine in a mixed solvent of dichloromethane and triethylamine, adding thionyl chloride solvent dropwise with stirring in an ice water bath, and the crude product Purify with silica gel column to obtain 5-fluorobenzo[c][1,2,5]thiadiazole. Dissolve 5-fluorobenzo[c][1,2,5]thiadiazole in an aqueous hydrobromic acid solution, add liquid bromine dropwise with stirring at room temperature, and then heat to reflux overnight. The crude product is purified by silica gel column to obtain compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole).
[0054] (2) 4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole (comp...
Embodiment 2
[0077] The chemical process formula in Example 2 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:
[0078]
[0079] (1) Compound 1 (6.24g, 20mmol), tributyl (thiophen-2-yl) tin (6.71g, 18mmol), toluene (50mL), DMF (10mL) and catalyst Pd (PPh 3 ) 4 (200mg) Under argon atmosphere, heating under reflux and stirring for 6 hours. After extraction with dichloromethane, the crude product was purified with a silica gel chromatography column, petroleum ether and dichloromethane were used as gradient elution mobile phases to obtain a yellow solid product (compound 8, yield 88.7%).
[0080] The NMR data of compound 8 are as follows: 1 HNMR(CDCl 3 ,600MHz)δ(ppm): 8.08(dd,J=3.7,1.1Hz,1H), 7.67(d,J=10.0Hz,1H), 7.51(dd,J=5.0,1.1Hz,1H), 7.19( dd,J=5.0,3.8Hz,1H).
[0081] (2) Compound 8 (1.78g, 5.0mmol), tributyl(4-(2-decyltetradecyl)thiophen-2-yl)tin (10.65g, 15.0mmol), catalyst Pd(PPh 3 ) 4 (100mg), toluene (50mL) and DMF (10mL) under argon...
Embodiment 3
[0092] The chemical process formula in Example 3 is shown in the following formula, and the specific reaction steps and reaction conditions are as follows:
[0093]
[0094] (1) Compound 1 (4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole) is disclosed in the literature (Adv.Mater.2012,24,3646-3649) The method is prepared. The specific steps are to dissolve commercially available 4-fluorobenzene-1,2-diamine in a mixed solvent of dichloromethane and triethylamine, and add thionyl chloride solvent dropwise with stirring in an ice water bath. The crude product was purified with silica gel column to obtain 5-fluorobenzo[c][1,2,5]thiadiazole. Dissolve 5-fluorobenzo[c][1,2,5]thiadiazole in an aqueous hydrobromic acid solution, add liquid bromine dropwise with stirring at room temperature, and then heat to reflux overnight. The crude product is purified by silica gel column to obtain compound 1 [4,7-dibromo-5-fluorobenzene[c][1,2,5]thiadiazole].
[0095] (2) 4,7-Dibromo-5-fluorobenzene[...
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