RESUMO
To prepare a novel highly photo-stable fluorescent chemosensor, curcumin was successfully immobilized to polyamidoamine dendrimer of zero (S1), first (S2) and second (S3) generations conjugated-UV absorber moieties. Chemical structure of synthesized chemosensors were well-analysed by FTIR, 1H-NMR, 13CNMR, elemental analysis, DSC and UV-vis techniques. Photo-physical characteristics and solvatochromism effect of three novel chemosensors in organic solvents with different dielectric constants ranged 2.21-37.78 were studied. The pH determination ability of S1, S2 and S3 in the range of 2-12 were also examined. Newly synthesized materials were employed for detection of different metal cations including Ag+, Ba2+, Cu2+, Ca2+, Cd2+, Fe3+, Hg2+, Ni2+, Pb2+ and Zn2+ and their possibility to apply as a cation chemosensor were evaluated. The results showed significant changes in their fluorescence intensity upon the different pHs and cations indicating their possibility to apply as a pH and metal cation chemosensor. Among the new chemosensors under study, S1 represented high sensitivity to pH in the range of 4-8 and high selectivity for Cu2+ over the other cations.
RESUMO
In this study, 4-amino-1,8-naphthalimide-conjugated polyamidoamine dendrimer was synthesized and characterized and its potentiality as a cation sensor was investigated. 4-Amino-1,8-naphthalic anhydride reacted with polyamidoamine dendrimer and the product was characterized using FTIR, (1)H NMR, (13)C NMR and melting point analysis method. The synthesized compound was applied to detect various cations in water media and N,N-dimethylformamide (DMF) via monitoring the quenching of the fluorescence intensity. Furthermore, various metal cations including Cu(2+), Ni(2+), Zn(2+), Pb(2+),Ca(2+), Ba(2+), Cd(2+), Hg(2+), Fe(2+), Fe(3+) and Ag(+) were tested. The complexes formed between the synthesized compound and metal cations in solution and their effects on Photoinduced Electron Transfer (PET) process were investigated regarding the potential application of the newly-synthesized dendrimer as a colorimetric and fluorescent sensor for such cations. The results clearly confirmed that the 1,8-naphthalimide groups surrounding the central dendrimer core showed strong green fluorescence emission at 553 nm. This effect considerably decreased with the introduction of all cations, except Ag(+) where the fluorescence quenching effect was remarkable and more dominant. Therefore, it can be concluded that the synthesized dye has the potentiality of being a highly sensitive and selective fluorescence sensor for Ag(+) cation.
