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Novel blue emitting tetra- and pentamethylpiperidin-4-yloxy-1,8-naphthalimides as photoinduced electron transfer based sensors for transition metal ions and protons
Two novel blue emitting 1,8-naphthalimides (1 and 2), containing 2,2,6,6-tetramethylpiperidin-4-yloxy moieties, and newly synthesized under phase transfer catalysis conditions 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)-1,8-naphthalimide 7, were configured as “fluorophore-spacer-receptor” systems. Basic photophysical characteristics of the novel fluorescent brighteners were investigated in both DMF and water/DMF (4:1, v/v) solution. Their ability to detect cations was evaluated in the presence of transition metal ions (Cu2+, Pb2+, Zn2+, Ni2+, Co2+) and protons. The presence of metal ions and protons was found to disallow a photoinduced electron transfer leading to an enhancement in the fluorophore emission intensity. The results clearly showed a good sensor activity towards transition metal ions and protons, especially of compound 7, containing tertiary amine receptor. This indicates the potential of the novel compounds as highly efficient “off-on” pH switchers and fluorescent detectors for metal ions.
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Reference£º
Piperidine – Wikipedia,
Piperidine | C5H10303N – PubChem