Hydrogen-Bonding-Induced Planar, Rigid, and Zigzag Oligoanthranilamides. Synthesis, Characterization, and Self-Assembly of a Metallocyclophane

Four oligoanthranilamides 1−4, which are incorporated with three, five, seven, or nine benzene
units, respectively, have been synthesized and characterized. X-ray analysis, 1D and 2D 1H NMR,
and IR experiments reveal that all the new oligoamides adopt rigid, planar and zigzagged
conformations in both solution and solid state, which are stabilized by intramolecular three-center
hydrogen bonding. A 5-mer oligomer 22, which is incorporated with two acetylene groups at the
ends, has also been synthesized and utilized for the self-assembly of a rigid hydrogen-bonded
metallocyclophane. The new rigid oligoanthranilamides represent useful building blocks for the
construction of supramolecular architectures.