Synthesis 2019; 51(22): 4147-4152
DOI: 10.1055/s-0039-1690687
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© Georg Thieme Verlag Stuttgart · New York

New Synthesis of a Dibenzoperylene Motif Featuring a Doubly Boron–Nitrogen-Doped Bay Region

Michael Fingerle
,
Simon Stocker
,
This research was funded by the Vector foundation. The authors acknowledge support by the state of Baden-Württemberg through bwHPC and the DFG through grant no INST 40/467-1 FUGG.
Further Information

Publication History

Received: 16 July 2019

Accepted after revision: 04 September 2019

Publication Date:
01 October 2019 (eFirst)

Abstract

A dibenzoperylene motif featuring a doubly boron–nitrogen-doped bay region is accessible from an aniline derivative in six steps in good overall yield. Two n-butyl groups provide the BN-doped polycyclic aromatic hydrocarbon with sufficient solubility in common organic solvents. The synthesis sequence allows installation of a second boron atom next to a weakly nucleophilic nitrogen by using a protected boron species. The title compound shows blue fluorescence, an extremely high fluorescence quantum yield, and an interesting doped bay region.

Supporting Information

 
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