Efficient Synthesis of 2,7-Dibromocarbazoles as Components for Electroactive Materials

Abstract

An efficient two-step synthesis of 2,7-dibromocarbazole is reported. Nitration and Friedel-Crafts acylation of 2,7-dibromo­carbazole proceed readily at the activated 3 and 6 positions to give new multifunctionalised carbazoles, which are of interest as monomers for new electrically active organic materials.

Key words

carbazole - heterocycles - electrophilic aromatic substitution - polymers - conjugation

References

• 1 Kraft A. Grimsdale AC. Holmes AB. Angew. Chem. Int. Ed.  1998,  37:  402 
• 2 Brabec CJ. Sariciftici NS. Hummelen JC. Adv. Funct. Mater.  2001,  11:  15 
• 3 Dimitrakopoulos CD. Malefant PR. Adv. Mater.  2001,  14:  99 
• 4a Morin J.-F. Leclerc M. Macromolecules  2001,  34:  4680 
• 4b Zotti G. Schiavon G. Zecchin S. Morin J.-F. Leclerc M. Macromolecules  2002,  35:  2122 
• 5 Yamato T. Hideshima C. Suehiro K. Tashiro M. Prakash GKS. Olah GA. J. Org. Chem.  1991,  56:  6248 
• 6 Shaw RS. Turner EE. J. Chem. Soc.  1932,  285 
• 7 Cadogan JIG. Cameron-Wood M. Makie RK. Searle RJG. J. Chem. Soc.  1965,  4831