New [5]helicene derivatives with large Stokes shifts for Hg2+ determination and their application in drinking water, river water and tuna fillet

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Anuwut Petdum
Jitnapa Sirirak
Vannajan Sanghiran Lee
Hubert A. Nienaber
Waraporn Panchan
Thanasat Sooksimuang
Nantanit Wanichacheva

Abstract

Two novel [5]helicene-based fluorescence sensors, H1 (2,2'-((propane-1,3-diylbis(sulfanediyl))bis(ethane-2,1-diyl))bis(7,12-dimethoxy-4,5,14,15-tetrahydro-1H-dinaphtho[2,1-e:1',2'-g]isoindole-1,3(2H)-dione) and H1A (2,2'-((propane-1,3-diylbis(sulfanediyl))bis(ethane-2,1-diyl))bis(7,12-dimethoxy-1H-dinaphtho[2,1-e:1',2'g]isoindole-1, 3(2H)-dione) were successfully prepared and characterized for their application in the determination of Hg2+ ions. The syntheses of H1 and H1A involved simple reactions including alkylation and imide formation. The spectroscopic results of H1 and H1A showed strong fluorescence in the visible region and large Stokes shifts (150-200 nm). Sensors provided Hg2+-selective fluorescence quenching by discriminating interfering ions including Cd2+, Co2+, Zn2+ Pb2+, Ag+ and Cu2+. The binding mode of the sensors was also explored using molecular modeling, In addition, H1 showed the potential to determine Hg2+ in real samples such as drinking water, river water and tuna fillet.

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