Water-Soluble Bis-triazolyl Benzochalcogendiazole Cycloadducts as Tunable Metal Ion Sensors

Abstract

A series of bis-triazolyl benzochalcogendiazoles was synthesized to investigate their metal-binding capabilities. These fluorophores were formed through the cycloaddition of an ethynylated benzochalcogendiazole and a water-soluble azide. Variation of the chalcogen heteroatom was seen to affect the photophysical properties as well as the metal-binding activity. These cycloadducts exhibited a distinct response to Cu(2+), Ni(2+), and Ag(+) in water. The binding affinity for the copper and nickel ions increased moving the chalcogen atom from O to Se. Statistical analysis of the spectral data enabled differentiation of Ag(+), Cu(2+), and Ni(2+) ions.

Dithiazolo[5,4‐b:4′,5′‐d]phosphole: A Highly Luminescent Electron‐Accepting Building Block

“…In particular, the triazole‐extended dithiazolophospholes provide a suitable N,N‐chelating moiety for metal‐ion binding. Similar chelating triazole systems for metal‐ion sensing have recently been reported by Bunz and co‐workers 26…”

Polymeric Chemosensors: A Conventional Platform with New Click Chemistry

“…Therefore, Bunz et al developed water-soluble fluorescent molecules possessing oligo-(ethylene oxide) substituents attached to the heteroaromatic core via a 1,2,3,-triazole linkage. 37 Thus, three bis-triazolyl benzochalcogendiazoles were synthesized to investigate their metal ion-complexation abilities (see Figure 13a). 37 These fluorophores were formed by the CuAAC cycloaddition between the ethynylated benzochalcogendiazole and water-soluble azidated oligo(ethylene oxide)s. Variation in the chalcogen heteroatom was found to affect the metal-complexation activity.…”

“…37 Thus, three bis-triazolyl benzochalcogendiazoles were synthesized to investigate their metal ion-complexation abilities (see Figure 13a). 37 These fluorophores were formed by the CuAAC cycloaddition between the ethynylated benzochalcogendiazole and water-soluble azidated oligo(ethylene oxide)s. Variation in the chalcogen heteroatom was found to affect the metal-complexation activity. It was clearly shown that the triazole rings are complexation sites for specific metal ions as shown in Figure 13b.…”

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

“…Reaction of aromatic and heteroaromatic ortho-diamines and selenium dioxide was conducted in solid state, 204,205 in ethanol, 20,[206][207][208][209][210][211][212] in acetic anhydride, 213 and even in water. [214][215][216] Typical examples of fused 1,2,5-selenadiazoles prepared are given in Figure 6 (solvents used and yields of selenadiazoles are shown below the formulae).…”

“…253 Statistical analysis of the spectrophotometric response of bis-triazolyl benzoselenadiazole 223 to the different metal ions resulted in a sensitive and selective sensor for silver, copper and nickel, ideal for use in aqueous systems ( Figure 11). 210 …”