Cyclic tetramers of 10-alkylanthracene-1,8-diyl units were synthesized by Ni-mediated coupling of the corresponding 1,8-dibromo precursors as new cycloarenes. X-ray analysis and DFT calculations revealed that these molecules had a box-shaped framework with dihedral angles between adjacent anthracene planes of ca. 70° and 110°. The macrocyclic framework had high conformational mobility compared with their analogs having ethynylene linkers. The UV-vis and fluorescence spectra indicated that the π-conjugation is not extended in the cyclic oligomers due to the nearly perpendicular conformation.
Box-shaped Cyclic Oligoarenes: Synthesis and Structure of Anthracene-1,8-diyl Cyclic Tetramers
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