Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

Long K San; Sebastian Balser; Brian J Reeves; Tyler T Clikeman; Yu-Sheng Chen; Steven H Strauss; Olga V Boltalina

doi:10.3762/bjoc.21.39

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

Beilstein J Org Chem. 2025 Mar 7:21:515-525. doi: 10.3762/bjoc.21.39. eCollection 2025.

Authors

Long K San¹, Sebastian Balser¹, Brian J Reeves¹, Tyler T Clikeman¹, Yu-Sheng Chen², Steven H Strauss¹, Olga V Boltalina¹

Affiliations

¹ Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
² ChemMatCARS, University of Chicago Advanced Photon Source, Argonne, IL 60439, USA.

Abstract

A new deep-blue emitting and highly fluorescent anthracene (ANTH) derivative containing perfluorobenzyl (Bn_F) groups, 9,10-ANTH(Bn_F)₂, was synthesized in a single step reaction of ANTH or ANTH(Br)₂ with Bn_FI, using either a high-temperature Cu-/Na₂S₂O₃-promoted reaction or via a room-temperature photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π-π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(Bn_F)₂, its significantly improved photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe.

Keywords: anthracene; dibromoanthracene; electron poor polyaromatic systems; fluorescence; perfluoroalkylation; perfluorobenzylation; photochemistry.