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Updated: Jun 6, 2025

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
A Helical Tubular Dyad of [9]Cycloparaphenylene: Synthesis, Chiroptical Properties and Post-Functionalization
Gaolei Li1, Liang-Liang Mao1, Jia-Nan Gao1
1Key Laboratory of Photochemical Conversion and Optoelectronic Materials, CAS-HKU Joint Laboratory on New Materials, Technical Institute of Physics and Chemistry, School of Future Technology, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing, 100190, China.
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 C3-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 1.47×103 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.
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