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

Four oligoanthranilamides <b>1</b>−<b>4</b>, which are incorporated with three, five, seven, or nine benzene units, respectively, have been synthesized and characterized. X-ray analysis, 1D and 2D <sup>1</sup>H 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 <b>22</b>, 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.