The synthesis of six new, functionalized 180 degrees pyridyl donor ligands and their coordination-driven self-assembly into supramolecular rectangles is reported. Three of the new donors have been functionalized with hydrophobic straight chain alkane units (C6, C12, and C18) while the remaining three have been functionalized with derivatized di-, tetra-, and hexaethylene glycol hydrophilic units (DEG, TEG, and HEG, respectively). The resulting self-assembled hydrophobic and hydrophilic supramolecular rectangles have been fully characterized by multinuclear NMR and electrospray ionization mass spectrometry. Molecular force field modeling suggests that the functionalized rectangles range in size from roughly 3.0 x 2.9 to 3.0 x 6.0 nm2 in size.