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 (1)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 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.
Zhu
Jiang
J
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Wang
Xiao-Zhong
XZ
Chen
Ying-Qi
YQ
Jiang
Xi-Kui
XK
Chen
Xin-Zhi
XZ
Li
Zhan-Ting
ZT