Naphthalimide trifluoroacetyl acetonate: a hydrazine-selective chemodosimetric sensor

Abstract

The trifluoroacetyl acetonate naphthalimide derivative 1 has been synthesized in good yield. In acetonitrile solution, compound 1 reacts selectively with hydrazine (NH₂NH₂) to give a five-membered ring. This leads to OFF–ON fluorescence with a maximum intensity at 501 nm as well as easily discernible color changes. Based on a readily discernible and reproducible 3.9% change in overall fluorescence intensity, the limit of detection for 1 is 3.2 ppb (0.1 μM), which is below the accepted limit for hydrazine set by the U.S. Environmental Protection Agency (EPA). Compound 1 is selective for hydrazine over other amines, including NH₄OH, NH₂OH, ethylenediamine, methylamine, n-butylamine, piperazine, dimethylamine, triethylamine, pyridine, and is not perturbed by environmentally abundant metal ions. When supported on glass-backed silica gel TLC plates, compound 1 acts as a fluorimetric and colorimetric probe for hydrazine vapor at a partial pressure of 9.0 mm Hg, with selectivity over other potentially interfering volatile analytes, including ammonia, methylamine, n-butylamine, formaldehyde, acetaldehyde, H₂O₂, HCl, and CO₂ being observed. Probe 1 can also be used for the detection of hydrazine in HeLa cells and does so without appreciable interference from other biologically abundant amines and metal ions.