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

Abstract

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 ¹H NMR, ¹³C 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, ¹H NMR titration studies with uranyl nitrate revealed a binding constant of (2.1 ± 0.4) × 10² M⁻¹. These findings establish that such preorganized claw-shaped intermediates with preorganized cavities lay a critical foundation for developing advanced molecular cage architectures.