Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: A new molecular probe for ZnO nanoparticles with unusual fluorescence features

Laura Bekere, David Gachet, Vladimir Lokshin, Wladimir Marine, Vladimir Khodorkovsky

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Of a series of 4-substituted 1,8-naphthalimides, fluorescent 4-(6-piperidinyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzoic acid (4) was found to be a sensitive molecular probe for ZnO nanoparticles. We investigated in detail one- and two-photon absorption properties of this fluorophore. In nonpolar solvents, the acid 4 absorbs at about 400 nm and fluoresces at 500 nm with a fluorescence lifetime of about 7 ns, similar to the ester 6 and typical of the lifetimes of other derivatives of this type. Although the anionic form of this acid is not fluorescent, partial ionization of 4 in polar solvents, such as ethanol and acetonitrile, is not only accompanied by the expected decrease in the fluorescence quantum yield, but also gives rise to bathochromic shifts of both absorption and fluorescence and dual fluorescence with lifetimes of 0.2-0.3 ns and 6 ns ascribed to the formation of anionic complexes. The interaction with the ZnO surface brings about further considerable changes in the fluorescence patterns.

Original languageEnglish
Pages (from-to)1311-1318
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - 3 Jul 2013
Externally publishedYes

Keywords

  • 1,8-naphthalimide
  • Fluorescence
  • Hydrogen bond
  • One- and two-photon absorption
  • Zinc oxide

ASJC Scopus subject areas

  • Organic Chemistry

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