One system, three functions: an electroactive reconfigurable organic receptor for adaptive binding, information encoding, and metal-free oxidation

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.