Chromatographic separation by a new chelating resin containing ?-hydroxydithiocinnamic acid

Lih, Jin-Jou; Yeh, Kuo-Ying; Liu, Chuen‐Ying

doi:10.1007/bf00348506

Cited by 7 publications

(3 citation statements)

References 9 publications

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“…These types of dual-function compounds are attractive candidates to directly prepare functional polymers for application as catalysts in a variety of organic reactions, [62,64,65] anti-leishmanial agents, [58] potential anti-cancer agent, [56,57,59,60] inhibitors of amyloid aggregation, [63] or in wastewater treatment due to the ability to act as chelating ligands for noble metals. [75] Furthermore, such complexes might find use in bio-imaging by replacing the Pt element with Ti and Gd. [76]…”

Section: Discussionmentioning

confidence: 99%

Dual Function of β‐Hydroxy Dithiocinnamic Esters: RAFT Agent and Ligand for Metal Complexation

Farh

Gruschwitz

Ziegenbalg

et al. 2022

Macromol. Rapid Commun.

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The reversible addition‐fragmentation chain‐transfer (RAFT) process has become a versatile tool for the preparation of defined polymers tolerating a large variety of functional groups. Several dithioesters, trithiocarbonates, xanthates, or dithiocarbamates have been developed as effective chain transfer agents (CTAs), but only a few examples have been reported, where the resulting end groups are directly considered for a secondary use besides controlling the polymerization. Herein, it is demonstrated that β‐hydroxy dithiocinnamic esters represent a hitherto overlooked class of materials, which are originally designed for the complexation of transition metals but may as well act as reversible CTAs. Modified with a suitable leaving group (R‐group), these vinyl conjugated dithioesters indeed provide reasonable control over the polymerization of acrylates, acrylamides, or styrene via the RAFT process. Kinetic studies reveal linear evolutions of molar mass with conversion, while different substituents on the aromatic unit has only a minor influence. Block extensions prove the livingness of the polymer chains, although extended polymerization times may lead to side reactions. The resulting dithiocinnamic ester end groups are still able to form complexes with platinum, which verifies that the structural integrity of the end group is maintained. These findings open a versatile new route to tailor‐made polymer‐bound metal complexes.

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Section: Discussionmentioning

confidence: 99%

Dual Function of β‐Hydroxy Dithiocinnamic Esters: RAFT Agent and Ligand for Metal Complexation

Farh

Gruschwitz

Ziegenbalg

et al. 2022

Macromol. Rapid Commun.

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“…In the majority of complexes reported so far, the coordination sphere of the metal is closely controlled through the use of bridging/chelating/monodentate ligands containing N/O/S donor atoms. − Dithioesters have found applications in ionic resins for the separation of transition-metal ions, for Ag + -selective membrane electrodes, and as hair-growing agents in combination with zinc . The β-oxodithioesters are strongly O ∧ S-chelating ligands and have been utilized to synthesize homo- and heteroleptic complexes with several transition metals, yielding a stable delocalized six-membered ring about the metal center. , The metal complexes of organosulfur ligands including those of β-oxodithioesters have served as catalysts in a variety of organic transformation reactions and also exhibited biological properties such as antileishmanial and anticancer activities .…”

Section: Introductionmentioning

confidence: 99%

Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes

Singh

Anamika

Rajput³

et al. 2020

Inorg. Chem.

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Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2] n (2), [Zn(L3)2] n (3) [Cd(L1)2] n (4), [Cd(L2)2] n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized by elemental analysis, IR, UV–vis, and NMR spectroscopy (1H and 13C{1H}). The solid-state structures of all complexes were ascertained by single-crystal X-ray crystallography. The β-oxodithioester ligands are bonded to Zn(II)/Cd(II) metal ions in an O∧S and N chelating/chelating–bridging fashion leading to the formation of 1D (in 2–4) and 2D (in 5) coordination polymeric structures, but complex 1 was obtained as a discrete tetrahedral molecule. Complex 4 crystallizes in the C2 chiral space group and has been studied using circular dichroism (CD) spectroscopy. The multidimensional assemblies in these complexes are stabilized by many important noncovalent C–H···π (ZnOSC3, chelate), π···π, C–H···π, and H···H interactions. The catalytic activities of 1–5 in reactions involving C–C and C–O bond formation have been studied, and the results indicated that complex 3 can be efficiently utilized as a heterogeneous bifunctional catalyst for the Knoevenagel condensation and multicomponent reactions to develop biologically important organic molecules. The luminescent properties of complexes were also studied. Interestingly, zinc complexes 1–3 showed strong lumniscent emission in the solid state, whereas cadmium complexes 4 and 5 exhibited bright luminescent emission in the solution phase. The semiconducting behavior of the complexes was studied by solid-state diffuse reflectance spectra (DRS), which showed optical band gaps in the range of 2.49–2.62 eV.

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“…The 3-hydroxy-3-( p -R-phenyl)-2-propenedithioic acid has shown different applications such as being the active moiety in ionic resins for transition metal ion separations, , in the development of new Ag + -selective membrane electrodes, , and as hair-growing agents using Zn as metallic center, among others. But in all cases, the complex structures have not been determined.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Tautomerism of Four Novel Copper(I) Complexes from 3-Hydroxy-3-(p-R-phenyl)-2-propenedithioic Acids

et al. 2004

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Chromatographic separation by a new chelating resin containing ?-hydroxydithiocinnamic acid

Cited by 7 publications

References 9 publications

Dual Function of β‐Hydroxy Dithiocinnamic Esters: RAFT Agent and Ligand for Metal Complexation

Dual Function of β‐Hydroxy Dithiocinnamic Esters: RAFT Agent and Ligand for Metal Complexation

Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes

Synthesis, Characterization, and Tautomerism of Four Novel Copper(I) Complexes from 3-Hydroxy-3-(p-R-phenyl)-2-propenedithioic Acids

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