Aqueous phosphate detection in real samples using NIR-triggered Diamino Bis-Benzimidazoquinoline fluorescence sensor: An experimental and theoretical approach

Abstract

The present work reports the design, synthesis, and sensing applications of Diamino bis-benzimidazoquinoline (DA-BISQ) derivatives. These compounds were synthesized in appreciable yield and characterized by FT-IR, 1H, and 13C NMR spectral and mass spectrometry. Optical studies revealed intriguing dual excitation properties: single excitations at λex 330-386 nm and double excitations at λex 660-772 nm in 10 % ethanol-water medium. The near-infrared excitation region λex 660-772 nm was particularly focused on the detection of F¯, Cl¯, Br¯, I¯, AcO ̄, ClO4¯, NO3¯, and HPO4¯ anions. Notably, selective fluorescence quenching ''OFF'' responses were observed for geometric anions like AcO¯, ClO4¯, NO3¯, and HPO4¯. Interestingly, the pyridine spacer-containing derivative 1c exhibited a unique fluorescence ''OFF-ON'' response for the phosphate ion. Cyclic voltammetry titration further corroborated the binding affinity towards phosphate. To demonstrate practical applicability, a thin-film strip of receptor 1c was fabricated and tested for effective phosphate sensing in human blood serum samples. Density functional theory calculations were performed to elucidate the sensing mechanism with the phosphate anion. The combined experimental and theoretical results suggest an internal charge transfer process between the receptor and the anion.

Keywords

• Benzimidazole
• Bis-quinoline
• Fluorescence
• Anion sensing
• Thin film
• DFT