A highly sensitive and selective off–on fluorescent chemosensor for Al3 + based on naphthalene derivative

A new dialdehyde (D) containing two emissive naphthalene and its [1 + 1] macrocycle with 1,2-diaminopropane were synthesized and characterized. The macrocycle was studied by 1H NMR, 13C NMR, COSY, HSQC, DEPT, mass spectrometry and microanalysis. The influence of metal cations such as Na+, K+, Cs+, Mg2 +, Ba2 +, Al3 +, Pb2 +, Cr3 +, Mn2 +, Fe3 +, Co2 +, Ni2 +, Cu2 +, Zn2 +, Cd2 +, Hg2 + and Ag+ on the photophysical properties of the macrocyclic system in DMF and DMF/H2O (9:1, v/v) mixture was investigated by means of emission spectrophotometry. The macrocycle L was found to be as an effective fluorescent sensor for Al3 + ions.

A new macrocyclic chemosensor (L) containing two naphthalene fluorophores has been synthesized. Macrocycle L possesses a high affinity and selectivity for aluminum ions by enhancement of the fluorescence emission.Figure optionsDownload as PowerPoint slideHighlights
► A novel fluorescent chemosensor (L) bearing two naphthalene groups was prepared.
► The macrocycle L was found to be as an effective fluorescent sensor for Al3 + ions.
► The mechanism can be described as intramolecular photoinduced electron transfer.