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
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 N 2Ar) resulted not only in tunable emissions from blue to the NIR domain but also in significantly enhanced emission quantum efficiency up to Φ = 50%.
Topics & Concepts
ChemistryHeliceneHeteroatomPhotochemistryLuminescenceRadicalAcceptorMoleculeCombinatorial chemistryOrganic chemistryOptoelectronicsRing (chemistry)PhysicsCondensed matter physicsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsAdvanced NMR Techniques and Applications