Synthesis and intramolecular FRET of perylenediimide–naphthalimide dendrons

• We synthesize novel perylenediimide–naphthalimide fluorescent probes.
• These FRET-based fluorescent probes exhibit efficient selectivity toward Fe(III) and protons.
• Large perylenediimide–naphthalimide dendrons provide a new opportunity for near-infrared fluorescent probes.

Two novel fluorescence resonance energy transfer-based perylenediimide–naphthalimide dendrons with perylenediimides as the energy acceptor, tertiary amines as the proton or metal receptor and naphthalimide as the energy donor were successfully synthesized. The dendrons exhibited high selectivity toward Fe(III) in the presence of various other metal cations and exhibited sensitivity to protons. A 1:2 stoichiometry was found for the complex formed by the probes and Fe(III) using a Job's plot and by non-linear least square fitting of the fluorescence titration curves. The probe molecules present abilities of fast fluorescence detection of Fe(III) and for the fluorescent detection of protons with high energy transfer efficiency of 96–98%.

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