Novel naphthalimide–aminobenzamide dyads as OFF/ON fluorescent supramolecular receptors in metal ion binding

Marco A. Landey-Álvarez, Adrián Ochoa-Terán*, Georgina Pina-Luis, Marisela Martínez-Quiroz, Milagros Aguilar-Martínez, José Elías-García, Valentín Miranda-Soto, José Zeferino Ramírez, Lorena Machi-Lara, Victoria Labastida-Galván, Mario Ordoñez

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


A series of novel naphthalimide–aminobenzamide (NAPIM-2ABZ) dyads 3 connected by different length polymethylene chains were synthesized and studied as fluorescent supramolecular receptors in metal ion binding. The photophysical properties were evaluated and compared with separated chromophores. The electronic absorption spectra of dyads 3 showed no interaction between chromophores in the ground state. The fluorescence quantum yields were lower in dyads 3 in comparison with N-propyl-2-aminobenzamide (8). The fluorescence quenching is attributed to a PET mechanism between fluorophores (from 2ABZ to NAPIM), which is dependent on the polymethylene chain length. In metal binding study was found a response towards transition metal ions such as Hg(II), Cu(II), Zn(II) and Ni(II). Dyad 3b presented selectivity towards Cu(II). The UV-vis, IR and 1H-NMR studies demonstrated the interaction with 2ABZ moiety in the ground state, and interestingly dyads with shorter polymethylene chains 3a (n = 0), 3b (n = 1) and 3c (n = 2) exhibited an OFF/ON fluorescence behaviour due to the PET inhibition and the quenching of 2ABZ fluorescence. Dyads 3d (n = 4) and 3e (n = 6) presented opposite response ON/OFF in the complex with metal ions evidencing the absence of PET in these dyads.

Original languageEnglish
Pages (from-to)892-906
Number of pages15
JournalSupramolecular Chemistry
Issue number11-12
StatePublished - 1 Dec 2016

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© 2016 Taylor & Francis.


  • PET
  • aminobenzamide
  • dyads
  • metal binding
  • naphthalimide


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