Photo-induced charge transfer emission in (E)-3-(4-dimethylamino-naphthalen-1-yl)-acrylic acid and its use as metal ions fluorosensor

Abstract

In this study, spectroscopic properties of (E)-3-(4-dimethylamino-naphthalen-1-yl)-acrylic acid (DMANAA) have been explored using absorption and emission spectroscopy in combination with quantum chemical calculations. In addition to the local emission, the molecule shows a red-shifted emission from the charge transfer state. The charge transfer emission band is found to be dependent on polarity and hydrogen-bonding ability of the solvents. This photo-induced charge transfer process has been explored theoretically at Density Functional Theory level using twisted intramolecular charge transfer model. Structural calculations and potential energy surfaces along the donor twist coordinate done by Density Functional Theory correlate well with the spectroscopic observations. Addition of metal ions to DMANAA solutions in acetonitrile solvent shows progressive quenching of the charge transfer band and growth of a blue-shifted band, making way for its use as a good fluorosensor for various metal ions.