Fluorogenic Hg²⁺-Selective Chemodosimeter Derived from 8-Hydroxyquinoline

Abstract

[reaction: see text] A new thioamide derivative of 8-hydroxyquinoline-benzothiazole was prepared, and its fluorogenic chemodosimetric behaviors toward transition-metal ions were investigated. The thioamide derivative showed highly Hg2+-selective fluorescence enhancing properties (167-fold) in 30% aqueous acetonitrile solution. The selective and sensitive signaling behaviors were found to originate from the Hg2+ ion induced transformation of the very weak fluorescent thioamide derivative into a highly fluorescent amide analogue.

Selective chromogenic and fluorogenic signalling of Hg2+ ions using a fluorescein-coumarin conjugate

“…A number of interesting systems capable of Hg 2þ -selective chromogenic or fluorogenic chemosensing have been reported [2]; many of these systems are based on wellestablished and unique molecular frameworks, such as crown ethers [3][4][5][6], calix [4]arenes [7], cyclams [8], squaraines [9], 8-hydroxyquinolines [10][11][12], 1,4-disubstituted azines [13], thioureas [14,15], 1,3-dithiole-2-thione [16], and fluoresceins [17,18]. More recently, a number of efficient Hg 2þ -selective chemosensing systems have been devised based on rhodamine lactam or thiolactone derivatives [19][20][21][22], and have utilized the selective ring opening or chemical transformation processes of the rhodamine hydrazide or lactam subunit [23].…”

A turn-on fluorescent chemosensor for Hg2+ based on phenanthroline fluorophore

“…Thus, effective detection of mercury is of great significance for biochemistry, environmental science and medicine, and considerable efforts have been devoted to this regard. Although some significant progress in the creation of the highly sensitive redox [5,6], chromogenic [7][8][9], or fluorogenic [10][11][12][13][14][15][16][17][18] probes for Hg 2+ has been achieved, it is also an important practical challenge to search for fluorophores for the determination of Hg 2+ with nice analytical performance characteristics.…”

Synthesis of a highly metal-selective rhodamine-based probe and its use for the in vivo monitoring of mercury

“…Because of their high sensitivity, simplicity and reproducibility, fluorescent chemosensor techniques [4][5][6][7][8] have been extensively employed for the detection of biologically important metal ions. However, most of the known mercury fluorescent chemosensors [9][10][11] do not meet the selectivity and sensitivity requirements for the in vivo, aqueous solution imaging assays.…”