Synthesis of Bioctacene‐Incorporated Nanographene with Near‐Infrared Chiroptical Properties

作者：Xiushang Xu, Rafael Muñoz‐Mármol, Serhii Vasylevskyi, Andrea Villa, Giulia Folpini, Francesco Scotognella, Giuseppe M. Paternò, Akimitsu Narita · 发表于：Angewandte Chemie International Edition · 年份：2023 · DOI：10.1002/anie.202218350 · 被引用次数：23 · 研究领域：Synthesis and Properties of Aromatic Compounds、Luminescence and Fluorescent Materials、Supramolecular Self-Assembly in Materials

Abstract We report the synthesis of a hexabenzoperihexacene (HBPH) with two incorporated octacene substructures, which was unambiguously characterized by single‐crystal X‐ray analysis. The theoretical isomerization barrier of the ( P , P )‐/( P , M )‐forms was estimated to be 38.4 kcal mol −1 , and resolution was achieved by chiral HPLC. Notably, the enantiomers exhibited opposite circular dichroism responses up to the near‐infrared (NIR) region (830 nm) with a high g abs value of 0.017 at 616 nm. Moreover, HBPH demonstrated NIR emission with a maximum at 798 nm and an absolute PLQY of 41 %. The excited‐state photophysical properties of HBPH were investigated by ultrafast transient absorption spectroscopy, revealing an intriguing feature that was attributed to the rotational and/or conformational dynamics of HBPH after excitation. These results provide new insight into the design of chiral nanographene with NIR optical properties for potential chiroptical applications.