Experimental and Theoretical Studies of Fluorescent "Turn Off" Sensor Functionalized With Carboxylic Acid and Naphthalene Group for Selective Detection of 2,4,6-Trinitrophenol.

Abstract

A fluorescent sensor, 5-((2-hydroxynaphthalen-1-yl)methyleneamino)benzene-1,3-dicarboxylic acid (coded as SB), containing both π-π interacting sites (such as π-electron-rich moieties) and hydrogen bonding (H-bonding) interacting sites (such as highly acidic protons) has been developed via high yield reflux method. It was characterized by the various analytical techniques such as Fourier transform-infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H-NMR), thermogravimetric analysis (TGA), field emission scanning electron microscope (Fe-SEM), elemental mapping, and UV - visible spectroscopy etc. The spectral response of the as-synthesized SB sensor has been investigated for various nitro explosives (NEs). It has been found that the SB sensor selectively and sensitive sense highly toxic 2,4,6-trinitrophenol (TNP) via the "turn-off" quenching response. Its limit of detection for TNP was calculated to be 30 ppb. Spectral overlap, detailed mechanistic studies for their mode of action, and density functional theory (DFT) calculations reveals that photo-induced electron transfer process (PET), fluorescence energy transfers process (FRET), and electrostatic interactions (i.e. H-bonding) are the key factors for the turn-off response of SB towards TNP. Notably, the synthesis of the sensor is cost-effective, energy efficient, and economic.