A Novel siloxane-containing dicarboxylic acid, 1,3-bis(p-carboxyphenylene-ester-methylene)tetramethyldisiloxane,and its derivatives: ester macrocycle and supramolecular structure with a copper complex

The new dicarboxylic acid, 1,3-bis(p-carboxyphenylene-ester-methylene)tetramethyldisiloxane (H₂L, 1) was obtained by treating 1,3-bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane with a mixture of terephthalic acid and terephthalic acid sodium salt in a 1:1 ratio. In this approach, besides the desired compound 1 (33 wt % yield), the condensation cyclic dimer 2 (7 wt % yield) and an oligomer 3 (10 wt % yield) resulted. The reaction between dicarboxylic acid H₂L, where L is the carboxylate ligand, along with imidazole as co-ligand, and copper hydroxide resulted in the formation of a coordination compound Cu(HIm)₄(H₂O)₂]L·4.5H₂O (4). Single-crystal X-ray crystallography has revealed that the crystal structure of 4 is a self-assembled H-bonded three-dimensional supramolecular structure. FTIR and NMR spectral techniques were also used to characterize the formed structures. Optical and thermal properties of all compounds were studied. The stability of the supramolecular structure in solution (methanol) and with temperature was studied using ATR-FTIR. The ability of the macrocycle 2 to bind potassium cations in solution was investigated by UV–vis spectrophotometry.