Colourful 3-amino-1,8-naphthalimide alkyl-substituted fluorescent derivatives

Abstract

The optical properties of four 3-amino-1,8-naphthalimide derivatives differing in the degree of substitution at the amino functionality were synthesised and studied by UV–visible absorbance and fluorescence spectroscopy in 1:1 (v/v) methanol/water and methanol. The compounds were structurally characterized by NMR, IR and HRMS. The charge transfer absorbance band was observed to shift to longer wavelength with increasing ethyl substitution. The emission band was also observed to shift to longer wavelengths with a decrease in the emission intensity with increasing ethyl substitution due to the peri effect. Irradiation of dye methanol solutions and in the solid state with a 365 nm UV lamp reveals distinct emission colours for each compound. Significantly larger Stokes shifts are observed in methanol than in mixed aqueous methanol. Quantum chemical calculations at the B3LYP/TZVP level of theory provided insight into the optimized ground state geometry, frontier molecular orbitals levels and solute-solvent dynamics revealing a stronger hydrogen bond between the 3-amino-1,8-naphthalimides and methanol in the lowest S1 excited state. The dyes were tested as fluorescent stains in MCF-7 cancer cells and observed to emit green emission in various organelles.