Abstract
Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn 2+ binding is an excellent way to detect its presence. A chemosensor for Zn 2+ based on dipicolylamine (DPA) groups connected by a pyridyl amide backbone has been synthesized. Addition of 2-chloroacetyl chloride to 2,6-diaminopyridine affords 2,6-bis(chloroethylamido)pyridine, which is converted to the sensor BADPA- P by 2,2′-dipicolylamine displacement of chlorine. This compound along with two others, the mono-DPA, ADPA- P and the benzyl in place of pyridyl, BADPA- B, present three potential Zn 2+ sensors. It was found that BADPA- P in the presence of Zn 2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd 2+, unlike with Zn 2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn 2+ ions bind to BADPA- P. Also, Zn 2+ enhances fluorescence even when other metal ions are present.
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