Facile synthesis, sensor activity and logic behaviour of 4-aryloxy substituted 1,8-naphthalimide

A series of 4-phenoxy- and 4-alkoxy-1,8-naphthalimide fluorophores have been synthesized in high yields at room temperature applying novel facile synthesis. One of the compounds was designed as a fluorescent PET sensor according to the "fluorophore-spacer-receptor" model. The ability of this molecule to detect protons and transition metal cations with pronounced selectivity towards Fe³⁺ was demonstrated. Moreover the 4-phenoxy substituted 1,8-naphthalimides were highly solvent sensitive and able to detect small quantities of water. The potential of the 1,8-naphthalimide sensor to execute INHIBIT logic function at molecular level was also demonstrated.