Add time:08/22/2019         Source:sciencedirect.com

To examine the consequences of nature and number of nitrogen atoms on metal ion sensing properties, four new molecular receptors based on 1-aminoanthracene-9,10-dione as chromogenic moiety and different types of nitrogen atoms viz. arylamine, alkylamine, and pyridyl nitrogen as appendages have been synthesized. These receptors in CH3OH/H2O (1:1) (v/v) at pH 7.0, on addition of heavy metal ions show selective and/or semi-selective interactions. These binding interactions are visible to naked eye due to remarkable color change and are associated with λmax shift by 85–125 nm. Molecular receptor 2, with two sp2 hybridized nitrogen atoms and one arylamine nitrogen, selectively binds with Cu2+ but 2-Cu2+ complex is stable only between pH 7.0 and 8.75. However, the conversion of imine nitrogen to alkylamine in molecular receptor 6, increases the binding ability toward Cu2+ along with significant binding affinities toward Ni2+ and Co2+. Receptor 6 shows the stability of its complexes in the order Cu2+>Ni2+>Co2+ in a broader pH range 6–12. Dipicolylamine based receptor 8, possessing two pyridyl nitrogen atoms, one tertiaryamine and one arylamine nitrogen atoms as ligating sites, also binds semiselectively in the order Cu2+>Co2+>Ni2+. Receptor 10, possessing anilide group in the place of arylamine in receptor 8, on addition of Cu2+, Ni2+ or Co2+ shows bathochromic shift of λmax associated with color change from yellow to russet (brown) and on addition of Zn2+ shows hypsochromic shift of its λmax associated with disappearance of yellow color. Additionally, all the four chemosensors show ratiometric response toward all these metal ions and thus increase the usability and the dynamic range of estimation.

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