Highly Selective Fluorescence Detection of Hydrogen Sulfide by Using an Anthracene‐Functionalized Cyclam–Cu^II Complex

Abstract

An anthracene-functionalised cyclam-copper(II) complex for the detection of HSin aqueous environments has been prepared. This probe displays poor fluorescence but can selectively and sensitively detect HSanions in water over other anions, biothiols and common oxidants such as H 2 O 2 through remarkably enhanced emission. This turn-on response in the presence of the HSanion is ascribed to a demetallation reac-[a] Centro de Reconocimiento Molecular y Desarrollo Tecnológico Supporting Information (see footnote on the first page of this article): General techniques, synthesis and characterisation of 1 and [Cu(1)] 2+ ; sensing features of [Cu(1)] 2+ ; cell viability assay of [Cu(1)] 2+ and fluorescence microscopy studies.

A Copper Porphyrin for Sensing H2S in Aqueous Solution via a “Coordinative‐Based” Approach

“…Typically, in the presence of H 2 S, literature copper complexes undergo a demetalation reaction with concomitant release of the organic ligand. [40] Coordination of organic bases to copper porphyrins have already been observed by Glazkov et al [53,54] …”

“…The fluorescence spectrum of CuPPIX is consistently weaker than that of the free porphyrin ligand ( Figure S2 in the Supporting Information), which is most likely due to the coordination of the free ligand to the paramagnetic Cu 2+ center. [40] Scheme 1.…”

“…generally produce fluorescence turn-on changes via H 2 Smediated precipitation of Mt-S. [1,[32][33][34][39][40][41][42] Despite all the advantages of the above mentioned probes (e.g. high selectivity and sensitivity), some shortcomings typically involve slow response and poor water solubility.…”

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

“…135 Thus, screening of probe performance in the presence of other RSS is especially important, since alternate combinations of fluorophores and receptors exhibit different properties. Additional probes utilizing the CuS precipitation strategy have been reported for fluorescein ( 68-69 ), 136,137 anthracene ( 70 ), 138 and dimeric phenanthrene-fused dipyrromethene ( 71 ). 139 A two-photon probe 72 consisting of a carbon nanodot functionalized with N-(2-aminoethyl)-N,N,N′-tris(pyridin-2-ylmethyl)ethane-1,2-diamine(TPEA), a ligand used for copper binding, was used to image exogenous H 2 S in model cellular systems and lung cancer tissue.…”

Supramolecular Chemistry: New chemodosimeters and hybrid materials for the chromo-fluorogenic detection of anions and neutral molecules

“…38 For this purpose the authors prepared probe 4 (see Figure 2. Using this approach, novel fluorescent sensors for the recognition of biologically relevant HS − anion were recently prepared (see Figure 2.6).…”