BODIPY-Derived Polymeric Chemosensor Appended with Thiosemicarbazone Units for the Simultaneous Detection and Separation of Hg(II) Ions in Pure Aqueous Media

Abstract

Developing a simple and cheap analytical method for the selective detection and quantitative separation of toxic ions present in aqueous media is the biggest challenge faced by the chemosensing research community. Here, a 5,5difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo-diazaborinine-derived water-soluble polymer integrated with thiosemicarbazone units was rationally designed and synthesized for the simultaneous detection and separation of Hg(II) ions in pure aqueous solution. The water-soluble polymer scaffold poly(N,N′-dimethyl acrylamide-co-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo-diazaborinine-2-carbaldehyde) was synthesized by reversible addition−fragmentation chain transfer polymerization, followed by post-polymerization modification with thiosemicarbazide, leading to the formation of the target probe, P1. The nonemitting P1 exhibited bright yellow emission upon exposure to Hg(II) ions, with a limit of detection as low as 0.37 μM. This turn-on emission behavior triggered by Hg(II) ions might originate from the suppression of isomerization around the CN bond of the thiosemicarbazone moiety caused by the formation of a coordination complex between P1 and Hg(II) ions. In addition, P1 displayed excellent selectivity toward Hg(II) ions over other metal cations. Finally, the selective removal of Hg(II) ions from an aqueous solution containing various metal ions was achieved by precipitation, which is probably caused by the fact that coordination complexes whereby Hg(II) ions acted as bridgeheads between P1 molecules had formed.

Fluorescent probe for mercury ion imaging analysis: Strategies and applications

“…In order to improve the water solubility of fluorescent probe, Haldar and co-workers developed probe 31a based on the BODIPY fluorophore and thiosemicarbazide was introduced as response group [92]. Probe 31a had no fluorescence emission due to the non-radiative inactivation process of the excited state caused by C = N isomerization.…”

Catalyst Halogenation Enables Rapid and Efficient Polymerizations with Visible to Near-Infrared Light

“…However, the BODIPY platform has been heavily examined for imaging, 33,34 sensing, 35 and photodynamic therapy 36,37 applications. These extensive studies have unveiled a remarkable range of optoelectronic properties for compounds bearing a BODIPY scaffold, showing peak absorption values from 500-900 nm (blue/green-NIR), extinction coefficients exceeding 5 x 10 4 M -1 cm -2 , and reduction and oxidation potentials that span from -2.40 to -0.35 V and 1.55 to 0.18 V (vs. Cp2Fe/Cp2Fe+), respectively.…”

BODIPY-based fluorescent polymeric probes for selective detection of Fe3+ ions in aqueous solution

“…Moreover, polymers constructed by these two ways have certain applications in detecting and removing heavy metal ions [9,10]. Haldar et al [11] have synthesized a water-soluble BODIPY side-chain polymer integrated Supplementary Information The online version contains supplementary material available at https:// doi. org/ 10.…”