Events The 15th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 15th International Electronic Conference on Synthetic Organic Chemistry

Published date

31 Oct, 2011

Citation

Oleg N Chupakhin, Vladimir L Rusinov, Dmitry S Kopchuk, Igor S Kovalev, Grigory V Zyryanov, Efficient Synthesis of 2,2\'-Dicarbazole-1,1\'-Biphenyl - Prospective Host Material for PHOLEDs, in Proceedings of The 15th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2011, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-15-00626

Facebook

Twitter

Efficient Synthesis of 2,2\'-Dicarbazole-1,1\'-Biphenyl - Prospective Host Material for PHOLEDs

Oleg N Chupakhin ^1,2

Vladimir L Rusinov ¹

Dmitry S Kopchuk ^1,2

Igor S Kovalev ¹

Grigory V Zyryanov ^1,2

1. Ural Federal University, 620002, Russia, Yekaterinburg, Mira St, 19,

2. I.Ya. Postovsky Institute of Organic Synthesis (Ural Division of the Russian Academy of Sciences), 620000, Russia, Yekaterinburg, S.Kovalevskoi St, 20-22

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

Benzopyran-2-ones as attractive scaffold for MAO inhibitors: synthesis, biological evaluation and docking studies

A computational study of phenylalanine interaction with guanidinium cation