TY - JOUR
T1 - Novel naphthalimide–aminobenzamide dyads as OFF/ON fluorescent supramolecular receptors in metal ion binding
AU - Landey-Álvarez, Marco A.
AU - Ochoa-Terán, Adrián
AU - Pina-Luis, Georgina
AU - Martínez-Quiroz, Marisela
AU - Aguilar-Martínez, Milagros
AU - Elías-García, José
AU - Miranda-Soto, Valentín
AU - Ramírez, José Zeferino
AU - Machi-Lara, Lorena
AU - Labastida-Galván, Victoria
AU - Ordoñez, Mario
N1 - Publisher Copyright:
© 2016 Taylor & Francis.
PY - 2016/12/1
Y1 - 2016/12/1
N2 - 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.
AB - 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.
KW - PET
KW - aminobenzamide
KW - dyads
KW - metal binding
KW - naphthalimide
UR - http://www.scopus.com/inward/record.url?scp=84961205750&partnerID=8YFLogxK
U2 - 10.1080/10610278.2016.1149180
DO - 10.1080/10610278.2016.1149180
M3 - Artículo
AN - SCOPUS:84961205750
SN - 1061-0278
VL - 28
SP - 892
EP - 906
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
IS - 11-12
ER -