A BODIPY-based colorimetric and fluorometric chemosensor for Hg(ii) ions and its application to living cell imaging

Abstract

A new monostyryl boron dipyrromethene derivative (MS1) appended with two triazole units indicates the presence of Hg(2+) among other metal ions with high selectivity by color change and red emission. Upon Hg(2+) binding, the absorption band of MS1 is blue-shifted by 29 nm due to the inhibition of the intramolecular charge transfer from the nitrogen to the BODIPY, resulting in a color change from blue to purple. Significant fluorescence enhancement is observed with MS1 in the presence of Hg(2+); the metal ions Ag(+), Ca(2+), Cd(2+), Co(2+), Cu(2+), Fe(2+), Fe(3+), K(+), Mg(2+), Mn(2+), Ni(2+), Pb(2+), and Zn(2+) cause only minor changes in the fluorescence of the system. The apparent association constant (K(a)) of Hg(2+) binding in MS1 is found to be 1.864 × 10(5) M(-1). In addition, fluorescence microscopy experiments show that MS1 can be used as a fluorescent probe for detecting Hg(2+) in living cells.

Optical methods for the detection of heavy metal ions

“…108 The coordination of mercury results in a hypsochromic shift of the absorption band from 606 to 577 nm caused by the inhibition of the intramolecular charge transfer from nitrogen to the BODIPY moiety, inducing blue to purple change in the solution colour. The complex formation with mercury also increases the fluorescence intensity at 650 nm (by a factor of 65 upon the addition of 1.5 equiv.…”

A rhodamine-based chemosensor with diphenylselenium for highly selective fluorescence turn-on detection of Hg2+in vitro and in vivo

“…12 Fluorescence chemosensors provide a direct way for mercury detection due to their high sensitivity, selectivity, and their applications in environmental and biological analysis. [13][14][15][16][17][18][19][20][21][22][23][24][25] Among various available uorophores, rhodamine is remarkable due to its exceptional optical properties, such as a long absorption and emission wavelength, high extinction coefficient and quantum yield, and low detection limit. 4,26 Furthermore, rhodamine exists in two forms, a spirolactam (non-uorescent) form and a ring-opened amide (uorescent) form, providing an ideal model for the design of metal ion sensing with light "off-on" switching.…”

A Turn‐on Fluorescence Probe For Rapid, Sensitive And Visual Detection of Formaldehyde

“…Perylenebisimide (PDI) have generated great interest in the field of fluorescent materials, owing to their excellent photo‐stability, high luminescence efficiency, novel optoelectronic properties, low cytotoxicity and strong intramolecular π‐π aggregation effect . PDI are also good electron acceptor, several PDI‐based probes based on photo‐induced electron transfer (PET) should be promising candidate for fluorophore in probes .…”