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Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 917-929

Published online 2012-02-09

Construction of novel molecular architectures from anthracene units and acetylene linkers

Shinji Toyota

Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan

Abstract: To create novel π-conjugated compounds, we constructed various molecular architectures from anthracene units and acetylene linkers. Several cyclic oligomers ranging from dimers to dodecamers were synthesized by macrocyclization of acyclic precursors with metal-catalyzed coupling reactions. The structures, dynamic behavior, and spectroscopic features were greatly influenced by the number of anthracene units and the combination of building units and linkers. Optically active and circular dichroism (CD)-active enantiomers of some chiral cyclic oligomers were resolved by chiral high-performance liquid chromatography (HPLC). Conformational analysis of hexamers and higher oligomers was performed with the aid of density functional theory (DFT) calculations. Acyclic oligomers underwent reversible folding–unfolding processes via photochemical and thermal reactions. These results suggest that transannular π–π interactions between anthracene units are important factors in controlling the structural and spectroscopic properties and functions of π-conjugated compounds. The scope and perspectives of this molecular design are discussed on the basis of previous studies.