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Efficient Synthesis of 2,2\'-Dicarbazole-1,1\'-Biphenyl - Prospective Host Material for PHOLEDs
Published: 31 October 2011 by MDPI in The 15th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: 2,2\'-Dicarbazole-1,1\'-diphenyl (2,2\'-CBP) is a prospective host material for phosphorescent light emmiting diodes (PHOLED)s. The synthesis of 2,2\'-CBP is limited by the availability of starting materials. We wish to report an efficient protocol for the synthesis of 2,2\'-CBP with overal yield about 90% starting from o-nitrobenzoic acid. Thus, Pd catalized homocoupling of o-nitrobenzoic acid affords 2,2\'-dinitro-1,1\'-diphenyl (2,2\'-DNDP) in 95% yield. Pd catalized reduction of 2,2\'-DNDP and the following double arylation of 2,2\'-diaminodiphenyl with 2,2\'-dibromo-1,1\'-diphenyl (which can be obtained from 2,2\'-diamino-1,1\'-diphenyl in 70-76% yield) affords the final product in 95% yield with overal yield after 3 steps of 90 %.
Keywords: 2,2\'-CBP, Pd coupling, PHOLEDs