Issue 12, 2023

Straightforward and regiospecific synthesis of 1,3,5,7-tetra-arylated acene bearing different aryl groups

Abstract

Multiple arylated acene derivatives play an important role in organic electronic materials. In this study, we developed a protocol for the synthesis of 1,3,5,7-tetra-arylated acenes by combining conventional cross-coupling and unique regio-selective cross-dehydrogenative coupling (CDC) reactions. 1,3,5,7-Tetra-arylated acene derivatives with different aryl groups were synthesised by first introducing aryl groups at the 1,5-positions via conventional cross-coupling reactions and then selectively introducing pentafluorophenyl groups at the sterically favourable 3,7-positions via CDC reactions. The CDC reactions proceeded smoothly on the substrates with moderately electron-donating substituents at the 1,5-positions. The crystal structure and basic physical properties of the products were elucidated, and one of 1,3,5,7-tetra-arylated anthracenes was found to function as a light-emitting material in organic light-emitting diodes.

Graphical abstract: Straightforward and regiospecific synthesis of 1,3,5,7-tetra-arylated acene bearing different aryl groups

Supplementary files

Article information

Article type
Research Article
Submitted
24 Feb 2023
Accepted
03 May 2023
First published
16 May 2023

Org. Chem. Front., 2023,10, 2955-2962

Author version available

Straightforward and regiospecific synthesis of 1,3,5,7-tetra-arylated acene bearing different aryl groups

R. Sato, K. Chen, T. Yasuda, T. Kanbara and J. Kuwabara, Org. Chem. Front., 2023, 10, 2955 DOI: 10.1039/D3QO00289F

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