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Polymers of ?-Caprolactone Using New Copper(II) and Zinc(II) Complexes as Initiators: Synthesis, Characterization and X-Ray Crystal Structures.

ABSTRACT: Five of six new Zn(II) and Cu(II) complexes were active in the ring-opening polymerization (ROP) of ?-caprolactone (CL) under solvent-free conditions, producing polycaprolactones (PCLs) of high crystallinity with molecular weights between 22,900 and 38,700 g mol^-1 and decomposition temperatures above 260 °C. ¹H NMR analysis demonstrated that the PCLs obtained were mainly linear, having hydroxymethylene groups at the chain ends. The results obtained indicated a significant improvement in terms of the ratio of monomer:initiator compared to related Cu(II) and Zn(II) complexes. In addition, the structures of the complexes 1 and 4 were determined by single-crystal X-ray diffraction. The synthesis and full characterization of all complexes are described in this paper.

SUBMITTER: Posada AF

PROVIDER: S-EPMC6401771 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Polymers of ε-Caprolactone Using New Copper(II) and Zinc(II) Complexes as Initiators: Synthesis, Characterization and X-Ray Crystal Structures.

Posada Andrés F AF Macías Mario A MA Movilla Santiago S Miscione Gian Pietro GP Pérez León D LD Hurtado John J JJ

Polymers 20181108 11

Five of six new Zn(II) and Cu(II) complexes were active in the ring-opening polymerization (ROP) of ε-caprolactone (CL) under solvent-free conditions, producing polycaprolactones (PCLs) of high crystallinity with molecular weights between 22,900 and 38,700 g mol<sup>-1</sup> and decomposition temperatures above 260 °C. ¹H NMR analysis demonstrated that the PCLs obtained were mainly linear, having hydroxymethylene groups at the chain ends. The results obtained indicated a significant improvement ...[more]

PMID: 30961164

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Project description:Synthesis, characterization, reactivity, and sensing properties of 4-formylbenzoate complexes of copper(II), zinc(II), and cadmium(II) possessing the 1,10-phenanthroline ancillary ligand are studied. The crystal structures of the (1,10-phenanthroline)bis(4-formylbenzoate)(aqua)copper(II) and (1,10-phenanthroline)bis(4-formylbenzo-ate)zinc(II) and a novel molecular complex comprising an assembly of mononuclear and dinuclear species of (1,10-phenanthroline)bis(4-formylbenzoate)cadmium(II) are reported. These zinc and cadmium complexes are fluorescent; they show differentiable sensitivity to detect three positional isomers of nitroaniline. The mechanism of sensing of nitroanilines by 1,10-phenanthroline and the complexes are studied by fluorescence titrations, photoluminescence decay, and dynamic light scattering. A plausible mechanism showing that 1,10-phenanthroline ligand-based emission quenched by electron transfer from the excited state of 1,10-phenanthroline to nitroaniline is supported by density functional theory calculations. In an anticipation to generate a fluorescent d10-copper(I) formylbenzoate complex by a mild reducing agent such as hydroxylamine hydrochloride for similar sensing of nitroaromatics as that of the d10-zinc and cadmium 4-formylbenzoate complexes, reactivity of d9-copper(II) with hydroxylamine hydrochloride in the presence of 4-formylbenzoic acid and 1,10-phenanthroline is studied. It did not provide the expected copper(I) complex but resulted in stoichiometry-dependent reactions of 4-formylbenzoic acid with hydroxylamine hydrochloride in the presence of copper(II) acetate and 1,10-phenanthroline. Depending on the stoichiometry of reactants, an inclusion complex of bis(1,10-phenanthroline)(chloro)copper(II) chloride with in situ-formed 4-((hydroxyimino)methyl)benzoic acid or copper(II) 4-(hydroxycarbamoyl)benzoate complex was formed. The self-assembly of the inclusion complex has the bis(1,10-phenanthroline)(chloro)copper(II) cation encapsulated in hydrogen-bonded chloride-hydrate assembly with 4-((hydroxyimino)methyl)benzoic acid.

Dataset Information

Polymers of ?-Caprolactone Using New Copper(II) and Zinc(II) Complexes as Initiators: Synthesis, Characterization and X-Ray Crystal Structures.

Publications

Polymers of ε-Caprolactone Using New Copper(II) and Zinc(II) Complexes as Initiators: Synthesis, Characterization and X-Ray Crystal Structures.

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