TY - JOUR
T1 - Zinc selective chemosensor based on pyridyl-amide fluorescence
AU - Lee, Hong Gyu
AU - Lee, Ju Hoon
AU - Jang, Seung Pyo
AU - Park, Hyun Min
AU - Kim, Sung Jin
AU - Kim, Youngmee
AU - Kim, Cheal
AU - Harrison, Roger G.
N1 - Funding Information:
Financial support from Korean Science & Engineering Foundation (2009-0074066), Converging Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0082832), and Brigham Young University is gratefully acknowledged.
PY - 2011/10/21
Y1 - 2011/10/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=80052921581&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2011.08.049
DO - 10.1016/j.tet.2011.08.049
M3 - Article
AN - SCOPUS:80052921581
VL - 67
SP - 8073
EP - 8078
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 42
ER -