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The synthesis of six new, functionalized 180
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pyridyl donor ligands and their coordination-driven self-assembly into supramolecular rectangles is reported. Three of the new donors have been functionalizedwith hydrophobic straight chain alkane units (C
6, C
12, and C
18) while the remaining three have beenfunctionalized with derivatized di-, tetra-, and hexaethylene glycol hydrophilic units (DEG, TEG, andHEG, respectively). The resulting self-assembled hydrophobic and hydrophilic supramolecular rectangleshave been fully characterized by multinuclear NMR and electrospray ionization mass spectrometry.Molecular force field modeling suggests that the functionalized rectangles range in size from roughly3.0 × 2.9 to 3.0 × 6.0 nm
2 in size.