Chiral Luminescent Aza[7]helicenes Functionalized with a Triarylborane Acceptor and Near-Infrared-Emissive Doublet-State Radicals

Jiaxian Duan; Yafei Shi; Fei Zhao; Chenglong Li; Zhihua Duan; Niu Zhang; Pangkuan Chen

doi:10.1021/acs.inorgchem.3c02470

Chiral Luminescent Aza[7]helicenes Functionalized with a Triarylborane Acceptor and Near-Infrared-Emissive Doublet-State Radicals

Inorg Chem. 2023 Oct 2;62(39):15829-15833. doi: 10.1021/acs.inorgchem.3c02470. Epub 2023 Sep 15.

Authors

Jiaxian Duan¹, Yafei Shi¹, Fei Zhao¹, Chenglong Li¹, Zhihua Duan², Niu Zhang³, Pangkuan Chen¹

Affiliations

¹ Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering of the Ministry of Industry and Information Technology, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, China.
² Baoshan Animal Disease Prevention and Control Center, Baoshan 678000, Yunnan, China.
³ Analysis and Testing Centre, Beijing Institute of Technology, Beijing 102488, China.

PMID: 37713177
DOI: 10.1021/acs.inorgchem.3c02470

Abstract

This paper presents new chiral luminescent molecules (N7-BMes2 and N7-TTM) using configurationally stable aza[7]helicene (1) as a universal heteroatom-doped chiral scaffold. The respective reactions of electron-donating 1 with a triarylborane acceptor via palladium-catalyzed Buchwald-Hartwig C-N coupling and with the open-shell doublet-state TTM radical via nucleophilic aromatic substitution (S_N2Ar) resulted not only in tunable emissions from blue to the NIR domain but also in significantly enhanced emission quantum efficiency up to Φ = 50%.