Synthesis, Structural Characterization, and Reductive Cleavage of an Oxygen‐Containing Naphthyl Macrocycle

A small macrocycle comprising ether-bridged naphthyl units was prepared in a two-step synthesis. Single-crystal X-ray diffraction of two polymorphs are reported, one which showed multiple C−H⋅⋅⋅πnaphthyl interactions solvent molecule the cavity macrocycle. Chemical reduction led to C−O bond cleavages accompanied by Z/E isomerization. The resulting twofold negatively charged (E)-1,2-bis(2-naphthyl)ethylene fragment isolated as its potassium salts. Electronic characterization revealed singlet ground state, and marked distortion central ethylene unit observed upon electron uptake.