Background and overview of preparation and application of 1-pyreneboronic acid
1-Pyreneboronic acid is a boric acid derivative. Boric acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In the Suzuki coupling, aryl halides and aryl or vinyl borates or boronic acids are coupled using Pd(PPh3)4.
Preparation and application of 1-pyreneboronic acid
At -78°C and N2, an excess of 1.6 M n-BuLi (50 mL, 80 mmol) in hexane sodium perborate tetrahydrate was added to 1-bromopyrene ( 20.4g, 72.6mmol) in 500ml of dry tetrahydrofuran solution. The reaction mixture was then maintained at 0°C for 1 h and then cooled to -78°C. Trimethyl borate (10.4g, 100mmol) was added dropwise; then the solution was slowly heated to room temperature and stirred for 24h. 2N HCl (150 ml) was added and the mixture was stirred for a further 1 h. The reaction mixture was extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuum, and the residue (n-hexane) was recrystallized to obtain 12.5g of 1-pyreneboronic acid yellow solid (70%).
Preparation and application of 1-pyreneboronic acid
Preparation and application of 1-pyreneboronic acid Application 1.
CN201310701060.1 reports a method for preparing graphene dispersion using pyrenyl benzoic acid polyether ester amphipathic reagent, using polyethylene glycol monomethyl ether, p-aminobenzoic acid and 1-pyreneboronic acid as raw materials, through The esterification reaction obtains hydrophilic long-chain para-aminobenzoic acid polyether ester, and then introduces HBr which reacts with 1-pyreneboronic acid to prepare 3,5-dibromobenzoic acid polyethylene glycol monomethyl ether ester. Then react with pyrene boric acid to synthesize an amphiphilic (hydrophilic and lipophilic) graphite praseodymium carbonate stripper; dissolve this compound and graphene in a H2O/Et solution, conduct ultrasound twice, let it stand, and then centrifuge A stable graphene dispersion was obtained. The present invention does not require the oxidation and reduction of graphene, so it has minimal destructive effects on the graphene structure, and can give full play to the unique electrical and thermal conductivity properties of graphene; the prepared dispersion has good water phase stability, which is a good solution for graphene in the composite. Applications in the field of materials provide an effective way.
Preparation and application of 1-pyreneboronic acid Application 2.
CN201911178353.X discloses a small molecule electron acceptor material for organic solar cells, its preparation method and application. The small molecule electron acceptor material for organic solar cells includes 4,7-bis(2-pyrene-5-thienyl)-5,6-difluoro-2,1,3-benzothiadiazole, and has The structure shown in formula (I):
The preparation method includes: in the presence of a catalyst, 4,7-bis(2-bromo-5-thienyl)-5,6-difluoro-2,1,3-benzothiadis Suzuki coupling reaction occurs between azole and 1-pyreneboronic acid to generate 4,7-bis(2-pyrene-5-thienyl)-5,6-difluoro-2,1,3-benzothiadiazole. The small molecule electron acceptor material for organic solar cells provided by the invention has a simple synthesis process, high purity, wide sources of raw materials and low price, is suitable for large-scale production and application, and can achieve photovoltaic conversion efficiency comparable to that of fullerene derivatives.
References
[1] CN201310701060.1 Method for preparing graphene dispersion using pyrenyl benzoic acid polyether ester amphipathic reagent
[2] CN201911178353.X Small molecule electron acceptor material for organic solar cells, its preparation method and application
[3] [China invention, China invention authorization] CN201310096505.8 Indenophenylene derivatives and organic electroluminescent devices using them
