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A Geometrically Flexible Three-Dimensional Nanocarbon.

Chun TangHan HanRuihua ZhangLygia S de MoraesYue QiGuangcheng WuChristopher G JonesIsabel Hernandez RodriguezYang JiaoWenqi LiuXuesong LiHongliang ChenLaura BancroftXingang ZhaoCharlotte L SternQing-Hui GuoMatthew D KrzyaniakMichael R WasielewskiHosea M NelsonPenghao LiJ Fraser Stoddart
Published in: Journal of the American Chemical Society (2024)
The development of architecturally unique molecular nanocarbons by bottom-up organic synthesis is essential for accessing functional organic materials awaiting technological developments in fields such as energy, electronics, and biomedicine. Herein, we describe the design and synthesis of a triptycene-based three-dimensional (3D) nanocarbon, GFN-1 , with geometrical flexibility on account of its three peripheral π-panels being capable of interconverting between two curved conformations. An effective through-space electronic communication among the three π-panels of GFN-1 has been observed in its monocationic radical form, which exhibits an extensively delocalized spin density over the entire 3D π-system as revealed by electron paramagnetic resonance and UV-vis-NIR spectroscopies. The flexible 3D molecular architecture of GFN-1 , along with its densely packed superstructures in the presence of fullerenes, is revealed by microcrystal electron diffraction and single-crystal X-ray diffraction, which establish the coexistence of both propeller and tweezer conformations in the solid state. GFN-1 exhibits strong binding affinities for fullerenes, leading to host-guest complexes that display rapid photoinduced electron transfer within a picosecond. The outcomes of this research could pave the way for the utilization of shape and electronically complementary nanocarbons in the construction of functional coassemblies.
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