6-Polyamino-substituted quinolines: synthesis and multiple metal (CuII, HgII and ZnII) monitoring in aqueous media. Issue 17 (12th March 2019)

• Record Type: Journal Article
• Authors: Abel, Anton S.; Averin, Alexei D.; Cheprakov, Andrey V.; Roznyatovsky, Vitaly A.; Denat, Franck; Bessmertnykh-Lemeune, Alla; Beletskaya, Irina P.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 17(2019)
• Page Start: 4243
• Page End: 4260
• Publication Date: 2019-03-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00259f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Multi-signaling or multi-metal optical analysis of toxic metal ions under physiological conditions. Abstract : Chemoselective palladium-catalyzed arylation of polyamines with 6-bromoquinoline has been explored to prepare chelators for the detection of metal cations in aqueous media. The introduction of a single aromatic moiety into non-protected polyamine molecules was achieved using the commercially available Pd(dba)2 /BINAP precatalyst to afford nitrogen chelators, in which the aromatic signalling unit is directly attached to the polyamine residue. Water-soluble receptors were then synthesized using N -alkylation of these polyamines by hydrophilic coordinating residues. By combining rich photophysical properties of the 6-aminoquinoline unit with a high coordination affinity of chelating polyamines and a hydrophilic character of carboxamido-substituted phosphonic acid diesters in a single molecular device, we synthesized chemosensor5 for selective double-channel (UV–vis and fluorescence spectroscopies) detection of Cu II ions in aqueous media at physiological levels. This receptor is suitable for the analysis of drinking water and fabrication of paper test strips for the naked-eye detection of Cu II ions under UV-light. By increasing the number of donor sites we also obtained chemosensor6 which is efficient for the detection of Hg II ions. Moreover, chemosensor6 is also suitable for multiple detection of metal ions because it chelates not only Hg II but also Cu II and Zn II ions displaying different responses of emission in the presence of these three cations.