A Helical Tubular Dyad of [9]Cycloparaphenylene: Synthesis, Chiroptical Properties and Post‐Functionalization
Gaolei Li, Liang‐Liang Mao, Jia‐Nan Gao, Xueliang Shi, Zi‐Ye Huo, Jingxuan Yang, Wen Zhou, Hongwei Li, Hai‐Bo Yang, Chen‐Ho Tung, Li‐Zhu Wu, Huan Cong
Abstract
Abstract The bottom‐up synthesis of discrete tubular molecules that mimic the structural features of carbon nanotubes has been a long‐standing pursuit for synthetic chemists. As the shortest segments of armchair‐type carbon nanotubes, cycloparaphenylenes are regarded as ideal macrocyclic building blocks for achieving this goal. Here we report the synthesis of a helical tubular molecule featuring three diyne linkers between two site‐specifically functionalized [9]cycloparaphenylenes. Its C 3 ‐symmetrical, radially conjugated structure and solid‐state packing have been elucidated by spectroscopic and crystallographic characterizations. Notably, the resolved enantiomers display a circularly polarized luminescence brightness value of 1.47×10 3 M −1 cm −1 , which is among the highest values for chiral organic molecules. Furthermore, the diyne‐linked molecule could be directly converted into a thiophene‐linked helical molecule, demonstrating the post‐functionalization approach for the construction of chiral tubular molecules from cycloparaphenylenes.