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Design and Synthesis of Highly Photostable Yellow–Green Emitting 1,8-Naphthalimides as Fluorescent Sensors for Metal Cations and Protons

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Abstract

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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Abbreviations

HALS:

hindered amine light stabilizer

PET:

photoinduced electron transfer

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Acknowledgements

This work was supported by the National Science Foundation of Bulgaria (project VU-X-201/06). Vladimir Bojinov and Nikolai Georgiev also acknowledge the Science Foundation at the University of Chemical Technology and Metallurgy (Sofia, Bulgaria).

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Authors and Affiliations

  1. Department of Organic Synthesis, University of Chemical Technology and Metallurgy, Kliment Ohridsky 8, 1756, Sofia, Bulgaria

    Vladimir B. Bojinov & Nikolai I. Georgiev

  2. Institute of Science and Technology of Polymers, CSIC, Juan de la Cierva 3, 28006, Madrid, Spain

    Paula Bosch

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  1. Vladimir B. Bojinov
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Correspondence to Vladimir B. Bojinov.

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Bojinov, V.B., Georgiev, N.I. & Bosch, P. Design and Synthesis of Highly Photostable Yellow–Green Emitting 1,8-Naphthalimides as Fluorescent Sensors for Metal Cations and Protons. J Fluoresc 19, 127–139 (2009). https://doi.org/10.1007/s10895-008-0394-2

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