Synthesis and luminescent properties of new naphthoquinoline lactone derivatives

Abstract

The multicomponent reaction between tetronic acid (1), 2-aminoanthracene (2) and aromatic aldehydes (3) and the subsequent addition of DDQ produced a series of naphtho [2,3-f]quinoline lactone derivatives (5) in good yield. UV–Vis and fluorescence spectra of these derivatives are described. The optical absorption and emission properties of the compounds were studied in different solvents and pH. The results show that the naphthoquinoline derivatives have emission bands of 453–517 nm and one of them, compound 5d, had an unexpected bathochromic shift (597 nm) caused by an excited-state intramolecular proton transfer (ESIPT). The luminescent properties of 5d in different solvents and pH, although preliminary, indicate the potential use of this compound as a chemical sensor.