Synthesis, characterization and molecular recognition of molecular clips based on Triethylbenzene

Based on the 1,3,5-triethylbenzene scaffold, nine “catch doll clip” type intermediate were synthesized through ether, ester, and amide linkages bridging different functional groups. The structures of these compounds were characterized by 1 H NMR, 13 C NMR and HRMS. Their spatial structures were investigated through single-crystal X-ray diffraction and molecular simulations, revealing that the amide molecular clips exhibit a tripodal topological structure, qualifying as a precursor for novel molecular cages. Surface electrostatic potential distribution analysis demonstrated that this compound possesses a well-preorganized cavity providing multiple weak interaction sites for molecular recognition. Furthermore, 1 H NMR titration studies with uranyl nitrate revealed a binding constant of (2.1 ± 0.4) × 10 2 M −1 . These findings establish that such preorganized claw-shaped intermediates with preorganized cavities lay a critical foundation for developing advanced molecular cage architectures. Nine molecular clips were synthesized and their spatial structures were studied by single crystal diffraction. The amide molecular clips have good pre-organized cavities, which is crucial for the efficient construction of molecular cages. In addition, the binding ability of the molecular clips with uranyl nitrate was also studied. • Single-crystal X-ray diffraction revealed that amide-linked molecular clips adopt a tripodal topology with a preorganized C3-symmetric cavity. • Electrostatic potential analysis indicated the presence of an electron-rich cavity with multiple hydrogen-bonding sites, suitable for molecular recognition. • The quinoline-functionalized molecular clip (9) exhibited selective binding to uranyl ions, with a binding constant of 210 M −1 determined by 1 H NMR titration. • DFT calculations and non-covalent interaction analysis confirmed coordination and hydrogen-bonding interactions between the clip and uranyl ion. • This work provides a foundation for designing preorganized molecular clip precursors for advanced cage architectures.