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A Carbazole‐Centered Expanded Helicene Stabilized with Hexabenzocoronene (HBC) Units

Xinyue Wang, Jinku Bai, Yun‐Jia Shen, Zhi‐Ao Li, Han‐Yuan Gong

2024Angewandte Chemie International Edition20 citationsDOIOpen Access PDF

Abstract

Abstract The synthesis and stabilization of heteroatom‐doped nanocarbon molecules, such as carbazole‐containing (super)helicenes, present significant challenges due to the complexities involved in maintaining structural integrity and electronic functionality. In this study, we successfully synthesized a carbazole‐centered expanded tris‐hexabenzo[7]helicene ( 1 ) via a facile FeCl 3 ‐mediated Scholl coupling reaction. 1 exhibits both chemical and chiral stability and demonstrates fluorescence at 628 nm with a quantum yield of 0.40. Additionally, the enantiomers of 1 display pronounced chiroptical properties, including a distinct circular dichroism (CD) signal spanning from 300 to 600 nm. The absorption dissymmetry factor (| g abs |) is determined to be 2.98×10 −3 , while the circularly polarized luminescence brightness ( B CPL ) is measured as 32.50 M −1 cm −1 .

Topics & Concepts

HeliceneCarbazoleChemistryOrganic chemistryMoleculeSynthesis and Properties of Aromatic CompoundsDNA and Nucleic Acid ChemistryOrganic Electronics and Photovoltaics