A copper(II) ion-selective on-off-type fluoroionophore based on zinc porphyrin-dipyridylamino.
A new copper(II) fluorescent sensor 5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc (1) has been designed and synthesized by the Ullmann-type condensation of bromoporphyrin zinc with 2,2'-dipyridylamine (dpa) under copper powder as a catalyst as well as with K2CO3 as the base in a DMF solution. It consists of two separately functional moieties: the zinc porphyrin performs as a fluorophore, and the dpa-linked-to-zinc porphyrin acts as a selected binding site for metal ions. It displays a high selectivity and antidisturbance for the Cu2+ ion among the metal ions examined (Na+, Mg2+, Cr3+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Fe3+) and exhibits fluorescence quenching upon the binding of the Cu2+ ion with an "on-off"-type fluoroionophoric switching property. The detection limit is found to be 3.3 x 10(-7) M (3s blank) for Cu2+ ion in methanol solution, and its fluorescence can be revived by the addition of EDTA disodium solution. The design strategy and remarkable photophysical properties of sensor 1 help to extend the development of fluorescent sensors for metal ions.
Weng
Yan-Qin
YQ
MOE Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China.
Yue
Fan
F
Zhong
Yong-Rui
YR
Ye
Bao-Hui
BH
D003300:Copper / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008024:Ligands; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence
C524383:5,10,15,20-tetra((p-N,N-bis(2-pyridyl)amino)phenyl)porphyrin zinc; D005456:Fluorescent Dyes; D007477:Ions; D008024:Ligands; D008665:Metalloporphyrins; C017802:zinc hematoporphyrin; D003300:Copper