Copolymer containing benzothiophene-silole di(diazosulfide) and preparation method and application thereof
A technology of benzothiadiazole and benzodithiophene, which is applied in the field of benzodithiophene-thiarolodipolymers and its preparation, can solve the problems of low energy conversion efficiency and achieve narrow band gap and excellent current carrying Effects of sub-migration ability and structural flexibility, and excellent reduction reversibility
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Embodiment 1
[0067] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-dioctylbenzo[2,1-b:3,4-b']dithiophene -6,6 Dioctylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=50), denoted as copolymer P1, the structural formula is as follows:
[0068]
[0069] The preparation method comprises the following steps:
[0070] (1), the preparation method of 4,9-dibromo-6,7-dioctyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) (A1) includes the following Steps:
[0071]
[0072] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:
[0073]
[0074] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100mL thionyl chloride into a three-necked flask, stir and slowly add 2mL pyridine dropwise, heat and then reflux at 80~90°C for 24h , stop the reaction, heat to 80°C and spin evaporate excess thionyl chloride, then cool the reaction product to room temperature, pour it into a large amount of water, stir, filter, wash with water and then vacuum...
Embodiment 2
[0100] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-dioctyloxy-benzo[2,1-b:3,4-b'] Dithiophene-6,6-dioctylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=48), which is denoted as copolymer P2, and its structural formula is as follows:
[0101]
[0102] The preparation method comprises the following steps:
[0103] (1) Preparation of 6,6-dioctyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A1)
[0104] The specific operation is the same as step (1) in Example 1.
[0105] (2), the preparation method of 4,5-dioctyloxy-2,7-bis(tributyltin base)-benzo[2,1-b:3,4-b']dithiophene (B2) includes the following step:
[0106] Provide a compound D2 with a structural formula as shown in formula D2, namely 4,5-dioctyloxy-2,7-dibromobenzo[2,1-b:3,4-b']dithiophene;
[0107] Under the protection of nitrogen, compound D2 (6.05g, 0.01mol) and 65mL of tetrahydrofuran were added to the three-necked flask, and 8.0mL of n-butyl lithium in n-hexane (2.5M, ...
Embodiment 3
[0115] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-bis(n-eicosyl)-benzo[2,1-b:3,4 -b']dithiophene-6,6-dimethylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=29), denoted as copolymer P3, The structural formula is as follows:
[0116]
[0117] The preparation method comprises the following steps:
[0118] (1), the preparation method of 6,6-dimethyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A2) includes the following Steps:
[0119] According to the steps (1)-(4) of step (1) of Example 1, 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared.
[0120] Compound C2, ie, dimethyldichlorosilane, having the structural formula shown in formula C2 is provided.
[0121] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole (3.4g, 5mmol) and 50mL DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add 4.0mL of n-butyllithium n-hexane solution (2.5M, 0.01mol) dropwise, drop it over in 0.5 hours, co...
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