Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores

Junqiang Wei, Zhuoer Wang, Pengyao Xing () and Ye Zhu ()
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Junqiang Wei: National University of Singapore, Department of Chemistry, Faculty of Science
Zhuoer Wang: Shandong University, School of Chemistry and Chemical Engineering
Pengyao Xing: Shandong University, School of Chemistry and Chemical Engineering
Ye Zhu: National University of Singapore, Department of Chemistry, Faculty of Science

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Chiral organic chromophores are foundational for advanced optical and electronic devices. Despite the widespread use of N-aryl carbazoles in visible-luminescent materials, chiroptical applications of their atropisomers have remained underdeveloped due to the synthetic challenge of achieving remote atroposelectivity necessitated by extended π-systems. Here, we present a unified strategy for the efficient synthesis of enantioenriched N–C and N–N carbazole atropisomers. By integrating 13C NMR-based ligand parameterization, we achieve enantiotopic-group-selective coupling reactions that simultaneously incorporate tailored π-functionalities and establish axial chirality (up to >99:1 er) using synthetic pathways established in carbazole chemistry. Through covalent modulation and noncovalent complexation, we investigate novel chiroptical functions of carbazole atropisomers, including circular dichroism (CD), circularly polarized luminescence (CPL), charge-transfer CPL (CT-CPL), and circularly polarized thermally activated delayed fluorescence (CP-TADF). By establishing an electrostatic steering strategy for remote atroposelectivity, our work paves the way for integrating multifunctional carbazoles into advanced optical and optoelectronic technologies.

Date: 2025
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DOI: 10.1038/s41467-025-65243-8

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