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Delocalized organic π‐radicals are intrinsically amphoteric redox systems; however, achieving their multistage redox capability presents a challenge. In addition, their instability often hampers their synthesis, isolation, and characterization. Herein, we report the synthesis of a stable π‐extended nanographene π‐radical (NR1) and its isolation in the crystalline form. NR1 exhibits an unusual four‐stage amphoteric redox behavior, as revealed by cyclic voltammetry measurements. The stable charged species, including a cation and a radical dication, are characterized using spectroscopic methods. This study demonstrates that π‐extension could serve as a viable approach to unlock the multistage redox ability of delocalized organic radicals. [ABSTRACT FROM AUTHOR]

A strained triple nanohoop with a shared central benzene unit is synthesized using a threefold intramolecular ring‐closing approach. Among the five possible constitutional isomers, the isomer with the highest D3h symmetry is isolated, the structure of which contains three nanohoop blades and a central hexaphenylbenzene unit. The structure is elucidated using NMR spectroscopy and mass spectrometry. The optical and electrochemical properties are investigated, revealing a moderate fluorescence quantum yield of 40 %. A water‐soluble nanomaterial is prepared using a nanoparticle encapsulation method, and a fluorescence quantum yield of 10 % is retained, which demonstrates the potential of the nanomaterial in biological systems. [ABSTRACT FROM AUTHOR]

The construction of three-dimensional nanocarbon structures with well-defined molecular dynamics is a challenging yet rewarding task in material science and supramolecular chemistry. Herein, we report the synthesis of two highly defective, nitrogen-doped molecular cylinders, namely MC1 and MC2, with a length of 1.4 nm and 2.7 nm, respectively. These molecular cylinders are constructed by connecting the cycloparaphenylene endcaps and fused aromatic pillars using a cyclocondensation reaction, affording a distinct donor-acceptor structure. An X-ray crystallographic analysis reveals a tilted cylindrical shape for MC1, and nuclear magnetic resonance spectroscopy and calculations indicate the occurrence of a dynamic swinging motion in solution. The elongation of conjugation in the cylinders attenuates the charge transfer character in the first excited state, resulting in remarkable length-dependent photophysical properties., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)