Abstract
A chemical-to-electrochemical signal transduction is reported based on the tandem switching of a bis-acridinium macrocycle and a proflavine derivative. Molecular recognition triggers a simultaneous guest–host transformation converting the acridinium units into their redox-inactive acridane counterparts. This unusual switching mechanism arises from the multiresponsive nature of the acridinium receptor, complementary acid–base properties of the host and guest, and stabilization of a water-assisted transition state within the macrocyclic cavity. Coined as tandem guest host switching (TANGHOS), this mechanism was elucidated through a combination of 1H NMR, UV/vis spectroscopic, computational analyses (DFT, molecular dynamics simulations), and a microkinetic model. When grafted onto a gold surface, the bis-acridinium macrocycle enables the selective electrochemical detection of proflavine from a complex mixture with ten polycyclic aromatic hydrocarbons. Finally, a low coverage ratio still led to amplified electrochemical responses by surface confinement and reaction-coupled recognition.
Reference
Tandem Guest-Host Switching for Chemical-to-Electrochemical Signal Transduction
L. Lefrançois, E. S. Gauthier, S. Chapuis, X. Shen, M. Ely Namoro, C. Gourlaouen, A. Chaumont, V. Heitz, L. Ruhlmann, M. Frasconi, M. Hromadová, H.-P. Jacquot de Rouville
J. Am. Chem. Soc., 2026, 148, 18374−18382 – DOI: https://doi.org/10.1021/jacs.6c04229
Contact
Henri-Pierre Jacquot de Rouville (équipe Synthèse des Assemblages Moléculaires Multifonctionnels, LSAMM), Institut de Chimie de Strasbourg, UMR 7177.
