84227-51-0

Upstream product

• 36839-56-2 1,11-diiodo-3,6-9-trioxaundecane 
• 62-53-3 aniline 
• 34604-52-9 diethylene glycol dimesylate 
• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 112-60-7 Tetraethylene glycol 

Downstream Products

• 1268488-01-2 C₁₇H₂₁N₅O₅S 
• 938065-20-4 10-[4-(2,6-diphenylpyridin-4-yl)phenyl]-1,4,7-trioxa-10-azacyclododecane 

Relevant academic research and scientific papers

Anilinopyridine–metal complexes for the selective chromogenic sensing of cyanide anion

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.

Dyes that bear thiazolylazo groups as chromogenic chemosensors for metal cations

A family of dyes (L1-L6) that contain a thiazolylazo group as signalling subunit and several macrocyclic cavities with different ring sizes and type and number of heteroatoms as binding sites has been synthesized and characterized. Solutions of L1-L6 in acetonitrile show broad and structureless absorption bands in the 554-577 nm range with typicalmolar absorption coefficients that range from 20000 to 32000 M -1 cm-1. A detailed protonation study was carried out with solutions of L1, L2 and L5 in acetonitrile. Addition of one equivalent of protons to L1 and L2 resulted in the development of a new band at 425 and 370 nm, respectively, which was ascribed to protonation in the aniline nitrogen. In contrast, protonation of L5 resulted in a bathochromic shift of 25 nm of the absorption band that was conceivable with protonation of one of the nitrogen atoms of the azo moiety. These results were in agreement with 1H NMR spectroscopic data. Theoretical studies on the model ligand L1 and on different possible protonation species were also performed by using density functional theory (DFT) quantum mechanical calculations. Colour modulations in solutions of L1-L6 in acetonitrile in the presence of the metal cations Fe3+, Ni2+, Zn2+, Cd2+, Pb2+ and Hg2+ have been studied. A selective chromogenic response of L4 in the presence of Pb2+ and L5 in the presence of Hg2+ was observed. To get a better insight into the chromophoric nature in the presence of metal cations, the interaction of Hg2+ with the model compound L1 in two different coordination modes was studied theoretically by using density functional theory (DFT) quantum mechanical calculations.

Multi-channel receptors and their relation to guest chemosensing and reconfigurable molecular logic gates

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.

1,4,7-Trioxa-10-azacyclododecane and Some N-Substituted Derivatives; Synthesis and Cation Complexing

Primary amines condense with 1,11-diiodo-3,6,9-trioxaundecane in acetonitrile solution containing dispersed Na2CO3 to give N-substituted derivatives of monoaza-12-crown-4, including several directly appended with an additional donor group.The unsubstituted azacrown and the N-methyl derivative were obtained from the N-benzyl derivative.The alkali cation complexing properties were studied by 13C NMR spectroscopy.It was found that the presence of an additional donor atom in the side-chain suppresses the formation of 2:1 in favour of 1:1 complexes.