Copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
A technology of benzothiadiazole and dithiophene, which is applied in the field of a[3,4-b]dithiophene-benzodipolymer and its preparation, can solve the problems of low energy conversion efficiency and achieve broad application prospects , excellent reduction reversibility, excellent carrier mobility and structural flexibility
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Embodiment 1
[0059] A copolymer containing a[3,4-b]dithiophene-benzobis(benzothiadiazole), that is, poly{4-octyl[3,4-b]dithiophene-6,7-di (3,7-Dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=52), denoted as copolymer P1, the structural formula is as follows :
[0060]
[0061] The preparation method comprises the following steps:
[0062] 1. Preparation of monomeric compound 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothio Oxadiazole), the structural formula is as follows:
[0063]
[0064] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:
[0065]
[0066] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100ml SOCl into the three-necked flask 2 , Stir and slowly add 2ml of pyridine dropwise, o-phenylenediamine cannot be completely dissolved at room temperature, the solution is orange, after heating, reflux reaction at 90°C for 24h, distill off excess SOCl 2 Finally, the mixture was cooled to room tempera...
Embodiment 2
[0091] A copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), that is, poly{4-n-eicosyl[3,4-b]dithiophene-6- Methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=24), denoted as copolymer P2, the structural formula is as follows:
[0092]
[0093] 1. Preparation of compound 4,9-dibromo-6-methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole);
[0094] To prepare the compound 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole, the steps (1)~(4) are the same as the steps (1)~( 4) the same.
[0095] (5) Preparation of compound 4,9-dibromo-6-methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole), the reaction formula is:
[0096]
[0097] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (6.8g, 10mmol) and 2-hexyne (1.64g, 20mmol) into the three-necked flask , 50ml DMF, stirred with nitrogen gas for 20min, added Bu 3 N (1.814g, 20mmol) and Pd(OAc) 2 (230mg, 1.0mmol), heated to 130°C, reacted at constant temperature for 4h, cooled, washed wit...
Embodiment 3
[0110] A kind of [3,4-b]dithiophene-benzobis(benzothiadiazole) copolymer, that is, poly{[3,4-b]dithiophene-6-(3,7-dimethyl base) octyl-7-n-eicosylbenzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=20), denoted as copolymer P3, the structural formula is as follows :
[0111]
[0112] 1. Preparation of compound 4,9-dibromo-6-(3,7-dimethyl)octyl-7-n-eicosyl-benzo[2,1-e:3,4-e]bis( benzothiadiazole);
[0113]Preparation of compound 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole, its steps (1)~(4) are the same as those in step 1 of Example 1 (1) ~(4) is the same.
[0114] (5) Preparation of 4,9-dibromo-6-(3,7-dimethyl)octyl-7-n-eicosyl-benzo[2,1-e:3,4-e]bis( benzothiadiazole), the reaction formula is:
[0115]
[0116] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (6.8g, 10mmol) into the three-necked flask, add 2,6 dimethyl-9-tri Decyne (8.94g, 20mmol), 80ml DMF, stirred with nitrogen for 20min, added Bu 3 N (1.814g, 20mmol) and Pd(OAc) 2 (230mg, 1.0mmol), heated...
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