Zinc selective chemosensor based on pyridyl-amide fluorescence

Hong Gyu Lee, Ju Hoon Lee, Seung Pyo Jang, Hyun Min Park, Sung Jin Kim, Youngmee Kim, Cheal Kim, Roger G. Harrison

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

Chemosensors are developed to image zinc ions. Fluorescence enhancement due to Zn2+ binding is an excellent way to detect its presence. A chemosensor for Zn2+ 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 Zn2+ sensors. It was found that BADPA-P in the presence of Zn2+ shows a large increase in fluorescence, whether in polar organic or aqueous environments. Its fluorescence in the presence of Cd2+, unlike with Zn2+, is not enhanced when excited at longer wavelengths. Proton NMR measurements, indicate two Zn2+ ions bind to BADPA-P. Also, Zn 2+ enhances fluorescence even when other metal ions are present.

Original languageEnglish
Pages (from-to)8073-8078
Number of pages6
JournalTetrahedron
Volume67
Issue number42
DOIs
StatePublished - 21 Oct 2011

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