Journal
JOURNAL OF FLUORESCENCE
Volume 19, Issue 1, Pages 127-139Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s10895-008-0394-2
Keywords
1,8-Naphthalimide; Fluorescence; Hindered amine light stabilizers; Photostability; Metal and proton sensors; Photoinduced electron transfer
Funding
- National Science Foundation of Bulgaria [VU-X-201/06]
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Two highly photostable yellow-green emitting 1,8-naphthalimides 5 and 6, containing both N-linked hindered amine moiety and a secondary or tertiary cation receptor, were synthesized for the first time. Novel compounds were configured as fluorophore-spacer-receptor systems based on photoinduced electron transfer. Photophysical characteristics of the dyes were investigated in DMF and water/DMF (4:1, v/v) solution. The ability of the new compounds to detect cations was evaluated by the changes in their fluorescence intensity in the presence of 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 dye fluorescence intensity. Compound 5, containing secondary amine receptor, displayed a good sensor activity towards metal ions and protons. However the sensor activity of dye 6, containing a tertiary amine receptor and a shorter hydrocarbon spacer, was substantially higher. The results obtained indicate the potential of the novel compounds as highly photostable and efficient off-on pH switchers and fluorescent detectors for metal ions with pronounced selectivity towards Cu2+ ions.
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