Macrocyclic 2,7-Anthrylene Oligomers

Chem Asian J. 2016 May 6;11(9):1370-5. doi: 10.1002/asia.201600230. Epub 2016 Mar 24.


A macrocyclic compound consisting of six 2,7-anthrylene units was successfully synthesized by Ni-mediated coupling of the corresponding dibromo precursor as a novel π-conjugated compound. This compound was sufficiently stable and soluble in organic solvents due to the presence of mesityl groups. X-ray analysis showed that the molecule had a nonplanar and hexagonal wheel-shaped framework of approximately S6 symmetry. The dynamic process between two S6 structures was observed by using the dynamic NMR technique, the barrier being 58 kJ mol(-1) . The spectroscopic properties of the hexamer were compared with those of analogous linear oligomers.

Keywords: NMR spectroscopy; arenes; conformation analysis; macrocycles; oligomerization.

Publication types

  • Research Support, Non-U.S. Gov't