84227-51-0Relevant articles and documents
Anilinopyridine–metal complexes for the selective chromogenic sensing of cyanide anion
Lozano-Torres, Beatriz,Marcos, M. Dolores,Pardo, Teresa,Sancenón, Félix,Martínez-Má?ez, Ramón,Rurack, Knut
, p. 786 - 796 (2018/02/19)
Probe 1, which contains an anilinopyridine chromophore and an aza-oxa macrocyclic subunit, presented an absorption band centered at 340 nm in acetonitrile. Addition of Fe(III), Cr(III) and Hg(II) induced the growth of a new absorption band at 430 nm (with color change from colorless to yellow), whereas in the presence of Cu(II), Zn(II) and Pb(II), less marked changes were observed. The color changes observed upon addition of Fe(III), Cr(III) and Hg(II) were ascribed to the formation of 1:1 stoichiometry complexes with probe 1. Coordination of Fe(III), Cr(III) and Hg(II) with the pyridine fragment of 1 induced an enhancement of the charge transfer character accompanied with a marked bathochromic shift that was reflected in a color change from colorless to yellow. The strength of the interaction between probe 1 and Fe(III) cation was modulated upon interaction with anions. Of all the anions tested, only cyanide was able to induce the bleaching of the yellow 1·Fe(III) complex solution. This bleaching was ascribed to the formation of 1·Fe(III)-CN complex that restored, to some extent, the optical features of the free probe allowing the chromogenic sensing of cyanide. Besides, 1·Fe(III) complex was used to detect cyanide in acetonitrile-water 90:10 v/v mixtures with good recoveries.
Multi-channel receptors and their relation to guest chemosensing and reconfigurable molecular logic gates
Jimenez, Diego,Martinez-Manez, Ramon,Sancenon, Felix,Ros-Lis, Jose V.,Soto, Juan,Benito, Angel,Garcia-Breijo, Eduardo
, p. 2393 - 2403 (2007/10/03)
The synthesis and characterisation of a family of multi-channel receptors containing crown-cation binding sites anchored to a 1-aminophenyl-1,2,2- tricyanoethylene group is reported. The ligands L1-L6bear a 1-aminophenyl-1,2,2-tricyanoethylene scaffolding which is simultaneously a redox-active group (showing reduction processes at moderately modest potentials) and an acceptor moiety in the 1-aminophenyl-1,2,2-tricyanoethylene chromophore. Additionally, dyes L1-L6 also show fluorescence emission. The colour variation of L1-L6 in acetonitrile in the presence of the metal cations Ag+, Cd2+, Cu2+, Fe2+, Hg2+, Pb2+ and Zn2+ has been studied. Selective hypsochromic shifts were found for the systems L 4-Pb2+, L5-Hg2+ and L 6-Hg2+ For Hg2+ with L5 and L 6 and Pb2+ with L4, emission fluorescence enhancements most likely associated with metal coordination to the anilinium nitrogen were observed. The electrochemical behaviour of receptors L 1-L6 was studied in acetonitrile with platinum as working electrode and [Bu4N][BF4] as supporting electrolyte. This family of receptors shows a one-electron reversible reduction process at around -0.70 V vs. SCE, attributed to the reduction of the tricyanovinyl group. Additionally, all the receptors also show the oxidation of the anilinium moiety at about 1.2-1.4 V vs. SCE. Significant anodic shifts of both reduction and oxidation waves were found in the presence of certain metal cations. The relationship of these multiple-channel signalling receptors with guest chemosensing and reconfigurable molecular-based logic gates is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
