Donor materials for polymer solar cells and polymerized monomers for donor materials
A technology for solar cells and polymerized monomers, applied to monomers with fused ring lactam structure and their preparation, and donor materials for polymer solar cells, can solve the problem of weak π-π interaction between chains, carrier mobility and low energy conversion efficiency, poor polymer stacking order, etc.
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Synthetic example 1
[0102] Synthesis Example 1: Compound TPTI is synthesized through the following reaction scheme:
[0103]
[0104] (1) Synthesis of intermediate a (2,5-dibromo-1,4-terephthaloyl chloride)
[0105] Add 2.33g of 2,5-dibromo-1,4-terephthalic acid (7.2mmol), 50mL of dichloromethane, 4mL of oxalyl chloride (45.6mmol) and 3 drops of N,N-dimethylform into a 100mL single-necked bottle Amide was stirred overnight at room temperature with the exclusion of moisture; dichloromethane and excess oxalyl chloride were spinned off, and the obtained white solid was directly used in the next reaction.
[0106] (2) intermediate b(2,5-dibromo-N 1 ,N 4 -Bis(2-hexyldecyl)-N 1 ,N 4 -Synthesis of two (thiophene-3)-1,4-terephthalamide
[0107] Intermediate a was dissolved in 20mL of dichloromethane, and 4.7g (14.5mmol) of N-(2-hexyldecyl)-3-aminothiophene was added dropwise under an ice-water bath. et al, Chem. Commun. 2012, 48, 3939-3941; 2. US Pat. 20100297405) and 2 mL of triethylamine in di...
Synthetic example 2
[0120] Synthesis Example 2: Compound c2 was synthesized by the following reaction scheme:
[0121]
[0122] (1) Synthesis of intermediate a2 (2,5-dibromo-3,4-thiophene dicarboxylic acid chloride)
[0123] Add 2.38g of 2,5-dibromo-3,4-thiophenedicarboxylic acid (7.2mmol), 50mL of dichloromethane, 4mL of oxalyl chloride (45.6mmol) and 3 drops of N,N-dimethylformamide into a 100mL single-necked bottle , and stir overnight at room temperature with the exclusion of moisture; spin off dichloromethane and excess oxalyl chloride, and the white solid obtained is directly used in the next reaction.
[0124] (2) intermediate b2 (2,5-dibromo-N 3 ,N 4 -Bis(2-hexyldecyl)-N 3 ,N 4 -Synthesis of bis(thiophene-3)-thiophene-3,4-dicarboxamide
[0125] Intermediate a2 was dissolved in 20 mL of dichloromethane, and a dichloromethane solution containing 4.7 g (14.5 mmol) N-(2-hexyldecyl)-3-aminothiophene and 2 mL of triethylamine (20 mL ). After stirring and reacting overnight at room tem...
Embodiment 3
[0129] The compound c2 obtained in Example 2 is used as a raw material for bromination to obtain compound d2, and the reaction scheme is as follows:
[0130]
[0131] Synthesis of product d2
[0132] Add c2 (288mg, 0.37mmol), 15mL chloroform and 10mL N,N-dimethylformamide to a 100mL two-necked flask, add 136mg N-bromosuccinimide under argon protection; stir at room temperature for 24 hours and pour into 150mL methanol , filtered with suction, and the crude product was purified by column chromatography using petroleum ether / dichloromethane (2:1) as the eluent to obtain 316 mg of a yellow solid (yield 91%).
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