One system, three functions: an electroactive reconfigurable organic receptor for adaptive binding, information...

Living systems rely on biomolecular receptors capable of selectively responding to multiple chemical cues, enabling precise information processing and adaptive functionality. Inspired by this paradigm, we report a multifunctional synthetic receptor that functions in stimuli-responsive conformational switching, programmable information encoding, and metal-free oxidation within a single molecular system. The receptor features a rigid, planar core that undergoes an unexpected and extensive deformation upon chemical alkylation, adopting a bowl-shaped geometry that can be fully reverted to its original flat structure upon guest recognition. This reversible transformation enables adaptive, induced-fit binding of diverse guest molecules, allowing the host to modulate its geometry to optimize donor-acceptor interactions and maximize complex stability. Electrochemical studies show that the resulting cationic species 1(PF₆)₃ is highly electron-deficient and serves as an efficient oxidant for metal-free oxidative transformations. Furthermore, the programmable conformational and redox states of the receptor provide a basis for constructing tunable donor-acceptor systems capable of molecular-level information encoding and decoding.