Porous organic material from discotic tricarboxyamide: side chain-core interactions.

The benzene-1,3,5-tricarboxyamide containing three L-methionine (1) self-assemble through 3-fold amide-amide hydrogen bonds and pi-pi stacking to fabricate one-dimensional nanorod like structure. However, the tyrosine analogue (2) carrying multiple H-bonding side chains lost the C-3 symmetry and 3-fold amide-amide hydrogen bonds and developed a porous structure. The porous material exhibits ten times more N-2 sorption (155 cc/g) than the columnar one, indicating that side chain-core interactions have a drastic effect on structure and function.