title: Chemistry of anthracene-acetylene oligomers: synthesis and enantiomeric resolution of a chiral 1,8-anthrylene-ethynylene cyclic tetramer.
abstract: To construct a new type of chiral pi-conjugated system, the title anthracene-acetylene oligomer containing two octyl groups at position 10 of 1,2-alternating anthracene groups was synthesized. Each anthracene unit was connected by Sonogashira coupling, and the tetrameric precursor was cyclized by a cross-coupling reaction to form the desired C2-symmetric compound. Its enantiomers were resolved by chiral HPLC with a Chiralcel OD column, and the chiroptical properties were investigated by optical rotation ([alpha]D(23) = -95 and +91) and circular dichroism (CD) measurements. The structural and spectroscopic features of this oligomer were discussed in terms of the molecular symmetry and the dynamic behavior of the macrocyclic framework.
authors.affiliation: Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Okayama, 700-0005, Japan. stoyo@chem.ous.ac.jp
authors.forename: Shinji
authors.initials: S
authors.lastname: Toyota
authors.forename: Shinya
authors.initials: S
authors.lastname: Suzuki
authors.forename: Michio
authors.initials: M
authors.lastname: Goichi