2-Methoxy-9H-carbazole

2-METHOXY-9H-CARBAZOLE is a white solid at room temperature and pressure, insoluble in water but soluble in strongly polar organic solvents. This compound belongs to the carbazole class of compounds, possessing a large conjugated system in its molecule and exhibiting good fluorescence properties. It is commonly used as an intermediate in organic synthesis. 2-Methoxycarbazole and its derivatives are widely used in the preparation of organic light-emitting materials, such as organic light-emitting diodes (OLEDs). In OLEDs, these compounds can serve as components of the fluorescent or emissive layers, emitting light of specific colors for display and lighting applications. Because its fluorescence properties can be tuned through chemical structure, organic light-emitting materials with different colors and properties can be designed.

To a suspension of copper(I)iodide (7.7 g, 40.6 mmol, 2.0 equiv) and 2-bromo-9H carbazole (5.0 g, 20.3 mmol, 1.0 equiv) in anhydrous DMF (22 mL), sodium methanolate (61 mL, 267 mmol, 13 equiv) was added. The reaction mixture was stirred for 4 hours at 120 °C. After completion (judged by TLC) the reaction mixture was filtrated through celites and directly adsorbed on silica. Purification by chromatography on silica (CHCl3 100 %) afforded the 2-methoxy-9H-carbazole (3.9 g, 19.5 mmol, 96 % yield) as a white solid.¹

[1] Limberg, F. R. P., Miasojedovas, A., Pingel, P., Reisbeck, F., Janietz, S., Monkman, A. P., & Krüger, H. (2015). Hole-transporting side-chain polystyrenes based on TCTA with tuned glass transition and optimized electronic properties†. RSC Advances, 101, 83122–83128. https://doi.org/10.1039/C5RA12963J