Star-shaped d-a-structured conjugated molecules based on benzotri(cyclopentadienobis-five-membered aromatic heterocycles) and their preparation methods and applications
A technology of cyclopentadiene and conjugated molecules, applied in the field of star-shaped D-A structure conjugated molecules, can solve the problems of unfavorable organic solar cell development, poor absorption of fullerene derivatives, limited chemical and electronic structure adjustability, etc.
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[0058] The present invention also provides a method for preparing a star-shaped D-A structure conjugated molecule based on benzotri(cyclopentadiene and double five-membered aromatic heterocycle), comprising the following steps:
[0059] (1) 2,5,8-tris(trimethyltin)benzotrithiophene and 2,5,8-tris(trimethyltin)benzotrifuran with a molar ratio of 1:3~15 Or 2,5,8-three (trimethyltin-based) benzotriselenophene, and 2-bromo-3 formate five-membered aromatic heterocyclic compound under the catalysis of palladium catalyst, in toluene solvent, 100 Coupling reaction at -120°C, the resulting compound and containing R 1 Group bromide, and active metal reagents for addition reaction, and then through the ring closure reaction to obtain the desired 1 The benzotri(cyclopentadiene and double five-membered aromatic heterocycle) core of the group;
[0060] (2) with R 1 The benzotri(cyclopentadiene and double five-membered aromatic heterocycle) central nucleus of the group directly undergoes ...
Embodiment 1
[0076] Example 1: A star-shaped D-A structure conjugated molecule based on benzotri(cyclopentadiene and double five-membered aromatic heterocycle) with a structure of BTCDT-3IC, the synthesis route is as follows:
[0077]
[0078] (1) Synthesis of an intermediate whose chemical structure is a: under argon protection, (3.8g, 17.1mmol) methyl 2-bromothiophene-3-carboxylate, (2.8g, 3.8mmol) 2,5,8 - Add tris(trimethyltin-based)benzotrithiophene and (0.22g, 0.19mmol)tetrakis(triphenylphosphine)palladium into a 250mL two-necked flask, then add 150mL deoxygenated toluene, stir and heat to 110°C Reaction 72h. Stop the reaction, add 100mL KF aqueous solution and stir for 1 h, extract with chloroform, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, spin dry after filtration, separate by column chromatography, the eluent is petroleum ether / ethyl acetate (volume ratio 5 : 1), obtain yellow solid product 2.0g, yield 80%. 1 H NMR (400MHz, CDCl ...
Embodiment 2
[0083] Embodiment 2: a star-shaped D-A structure conjugated molecule based on benzotri(cyclopentadiene and double five-membered aromatic heterocycle) whose structure is BTCDT-3ICF2, the synthetic route is as follows:
[0084]
[0085] Wherein, the synthesis of intermediates a, b, c, and d is the same as in Example 1.
[0086] Synthesis of BTCDT-3ICF2: Under argon protection, (0.3 g, 0.2 mmol) intermediate d and (0.55 g, 2.4 mmol) 5,6-difluoro-(1,1-dicyanomethylene-3- Indanone) was added to a 100 mL two-necked bottle, and then 100 mL of chloroform was added to completely dissolve it. Take 1.5 mL of pyridine with a syringe and add it to the reaction system. Heated to 65°C for 12h. Stop the reaction, add 150mL chloroform, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, spin dry after filtration, and separate by column chromatography, the eluent is petroleum ether / chloroform (volume ratio 1:1.5), to obtain 0.16g of red-black solid , the yield i...
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