Design of a Highly Selective Benzimidazole-Based Derivative for Optical and Solid-State Detection of Zinc Ion.

A novel series of benzimidazole-based molecules mimicking biological receptors, which exhibit selective coordination with zinc ions, were designed and synthesized. The photochromic behavior of these derivatives with various metal ions suggests a selective interaction of one of the receptors 2-(pyridin-2-yl)-4,7-di(thiophen-2-yl)-3 H -benzo[ d ]imidazole ( 2c ) with zinc ion. The lower limit of detection by photoluminescence quenching was determined to be 16 nM. The mechanism of selective complexation was elucidated by 1 H nuclear magnetic resonance titrations and dynamic light scattering analysis. The stoichiometry of the formation of the Zn(2c) 2 complex was evaluated by single-crystal X-ray diffraction and mass spectral techniques and calculated to be 2:1 (L:M). A change in the electronic energy levels on the sensor analyte interaction was observed by both ultraviolet photoelectron spectroscopy analysis and by density functional theory calculations, suggesting an electroactive semiconductor behavior. A symmetric Schottky structured sensor device was fabricated using the receptor 2c as the active sensing layer. A distinct change in current-voltage characteristics between the receptor and the complex suggests that the fabricated device could be used as a solid-state sensor for detecting zinc ion.