We propose strategies to construct chiral macrocycles by modification of the fundamental compound, 1,8-anthrylene-ethynylene cyclic tetramer, which features a diamond-prism structure. The incorporation of other anthracene units or diacetylene linkers produces structures of various symmetries. The enantiomers of some chiral derivatives could be resolved by chiral H PLC. The structures, dynamic behavior, and chiroptical properties of these macrocycles are summarized.