Uses
9-Carbazolylbenzeneboronic acid pinacol ester
Uses
9
H-Carbazole-9-(4-phenyl) boronic acid pinacol can be used as a donor molecule in the formation of novel donor-π-acceptor dyes for electrochemical applications. It can also be used in the formation of organic light emitting diodes (OLEDs).
General Description
9
H-Carbazole-9-(4-phenyl) boronic acid pinacol ester is a compound that is majorly used as an intermediate in electronic devices. Its molecular structure includes benzene rings, boronic acid pinacol ester and carbazole rings.
Synthesis
General procedure for the synthesis of 9-[4-(4-(4-bromophenyl)carbazole and pinacol ester of bis(boronic acid)]-9H-carbazole from 9-(4-bromophenyl)carbazole and pinacol ester of bis(boronic acid): 1 g of 9-(4-bromophenyl)carbazole (3.1 mmol), 0.79 g of pinacol ester of bis(boronic acid) (3.1 mmol), 30 mL 1,4-dioxane, 0.4 g of potassium acetate (4 mmol), and 0.13 g of [1,1'-bis(diphenylbenzene)-bis(diphenyloxy)-hexahydricyclic (1,1'-bis(diphenylbenzene))]-bis(bis(diphenylbenzene)) acid (4 mmol) , 30 mL of 1,4-dioxane, 0.4 g of potassium acetate (4 mmol), and 0.13 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (0.16 mmol), and the reaction was carried out for 48 hours at 85 °C. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of 200 mL of aqueous 3M hydrochloric acid. The organic layer was separated and washed with water. After the solvent was removed by evaporation, 1 g of the target product was purified by column chromatography with dichloromethane: petroleum ether = 1:2 (v/v) as eluent to give 1 g of the target product in 87% yield.
References
[1] Chemical Communications, 2012, vol. 48, # 71, p. 8970 - 8972
[2] Patent: CN108191739, 2018, A. Location in patent: Paragraph 0087; 0088; 0089
[3] Patent: EP1820801, 2007, A1. Location in patent: Page/Page column 88
[4] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 7, p. 1413 - 1421
[5] Patent: WO2012/37269, 2012, A1. Location in patent: Page/Page column 45-46
