A Colorimetric and Fluorimetric Chemodosimeter for Copper Ion Based on the Conversion of Dihydropyrazine to Pyrazine

Abstract

In this research, we successfully synthesized and fully characterized the new compound 5,8,13,16,21,24-hex-(triisopropylsilyl)ethynyl)-6,23-dihydro-6,7,14,15,22,23-hexaza-trianthrylene (HHATA, brown color in a mixed solvent of CH2 Cl2 /CH3 CN 1:1, v/v, weakly blue fluorescent), which can be easily oxidized to 5,8,13,16,21,24-hex-(triisopropylsilyl)ethynyl)-6,7,14,15,22,23-hexazatrianthrylene (HATA) (yellow color in CH2 Cl2 /CH3 CN 1:1, v/v), red fluorescent) by Cu(2+) ions. This reaction only proceeds efficiently in the presence of Cu(2+) ions when compared with other common metal ions such as Fe(3+) , Co(2+) , Mn(2+) , Hg(2+) , Ni(2+) , Pb(2+) , Ag(+) , Mg(2+) , Ca(2+) , K(+) , Na(+) , and Li(+) . Our result suggests that this reaction can be developed as an effective method for the detection of Cu(2+) ions.

Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics

“…Furthermore,ac hanged semiconducting behaviour,b ased on both electronic effects as well as the effect of the altering of crystal packings, [4] is observed. In addition, the donating properties of the nitrogen lone pair opens up several versatile applications,s uch as proton [5] and anion sensors, [6] sensors for cationic metal species, [7] and as chelating ligands for metal complexes. [8] Al arge part of N-containing polyaromatic compounds (N-PACs) is based on acene-related structures with pyrazine backbones.T his can be attributed to straightforward syntheses that are based on condensation methods [9] or palladiumcatalysed cross-couplings.…”

Modularer zweistufiger Zugang zu π‐erweiterten Naphthyridin‐Systemen – potente Bausteine für die organische Elektronik

“…[4] Darüber hinaus erçffnen die Donor-Eigenschaften des freien Elektronenpaars des Stickstoffs mehrere vielseitige Anwendungen, wie z. B. Protonen- [5] und Anionensensoren [6] sowie Sensoren fürk ationische Metallspezies [7] und als chelatisierende Liganden fürMetallkomplexe. [8] Ein großer Te il der Nhaltigen polyaromatischen Verbindungen (N-PAV s) basiert auf acenartigen Strukturen mit Pyrazin-Grundgerüst.…”

Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters

“…Whilst transition metal ion sensors generally rely on metal ion binding, chemodosimetric Cu(II) detection is receiving increasing attention. A range of chemistries including irreversible aryl ether cleavage, imine hydrolysis, redox chemistry inducing phenothiazine oxidation, dihydropyrazine oxidation, ring opening of rhodamine B derivatives and specific click ligation have been used to sense copper cations. Copper detection is amenable to a diverse range of assays including electrochemical, chromogenic and fluorogenic…”