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Poly(amidoamine) dendrimer peripherally modified with 4-N,N-dimethylaminoethyleneamino-1,8-naphthalimide as a sensor of metal cations and protons

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Abstract

A new poly(amidoamine) dendrimer from second generation whose periphery comprises sixteen fluorescent 4-N,N-dimethylaminoethylamino-1,8-naphthalimide units has been synthesized and characterized. In DMF, the dendrimer shows sensitivity to the presence of Cu2+, Fe3+ and protons. The changes in the fluorescence intensity of the material are in opposite directions if acids or metals are present. Fluorescence enhancements (FE from 5 to 9 depending on solvent) are recorded when the photoinduced electron transfer (PET) originating from the donating amine to the electron accepting naphthalimide is inhibited by the protonation of the N,N-dimethylamino groups. In the case of Cu2+ cations, a fluorescence quenching (FQ of 6) is first observed, followed by fluorescence partial restoration. In the Fe3+ case, the same behaviour is observed with a final FE of 2. The successive complexations of these cations by the dendrimer core and by the external rim of the dendrimer may explain the results.

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Authors and Affiliations

  1. Institute of Polymers, Bulgarian Academy of Sciences, ]1113, Sofia, Bulgaria

    Ivo Grabchev

  2. Université catholique de Louvain, Unité de Chimie des Matériaux Organiques et Inorganiques, Photochimie, Place Louis Pasteur, 1, B1348, Louvain la Neuve, Belgique

    Jean-Philippe Soumillion & Benoit Muls

  3. Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    Galya Ivanova

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  1. Ivo Grabchev
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  2. Jean-Philippe Soumillion
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Grabchev, I., Soumillion, JP., Muls, B. et al. Poly(amidoamine) dendrimer peripherally modified with 4-N,N-dimethylaminoethyleneamino-1,8-naphthalimide as a sensor of metal cations and protons. Photochem Photobiol Sci 3, 1032–1037 (2004). https://doi.org/10.1039/b412384k

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