Synthesis of Geminal Bis‐ and Tetrakisphosphonate Ester Derivatives and Their Coordination Behavior Towards Ca(II) Ions

Koehne, Ingo; Pietschnig, Rudolf

doi:10.1002/ejic.202200194

Cited by 5 publications

(2 citation statements)

References 63 publications

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“…Full details on the equipment, reagents used, synthesis of the starting products and characterisation data of the final compounds can be found in the Supplementary Materials. The Supplementary Materials contain the following references that are not mentioned elsewhere [37][38][39][40][41][42][43][44][45][46][47]. Under a nitrogen atmosphere, oxalyl chloride (1.32-2.64 equiv., 4.9-9.7 mmol) was added dropwise to a stirred solution of the corresponding phosphonate 1 (1 equiv., 3.7 mmol) in 20 mL dry DCM.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Backx,

Desmedt,

Dejaegere

et al. 2024

IJMS

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While organophosphorus chemistry is gaining attention in a variety of fields, the synthesis of the phosphorus derivatives of amino acids remains a challenging task. Previously reported methods require the deprotonation of the nucleophile, complex reagents or hydrolysis of the phosphonate ester. In this paper, we demonstrate how to avoid these issues by employing phosphonylaminium salts for the synthesis of novel mixed n-alkylphosphonate diesters or amino acid-derived n-alkylphosphonamidates. We successfully applied this methodology for the synthesis of novel N-acyl homoserine lactone analogues with varying alkyl chains and ester groups in the phosphorus moiety. Finally, we developed a rapid, quantitative and high-throughput bioassay to screen a selection of these compounds for their herbicidal activity. Together, these results will aid future research in phosphorus chemistry, agrochemistry and the synthesis of bioactive targets.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Backx,

Desmedt,

Dejaegere

et al. 2024

IJMS

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“…Phosphine oxides attracted great attention as promising extractants for 4(5)f-metal ions [ 15 , 16 , 17 , 18 , 19 , 20 ]. The chemistry of 1,3-bis-phosphine oxides is rapidly developing, which is mainly because bis(phosphine oxides) are efficient ligands allowing diverse complexation with lanthanide and calcium ions [ 21 , 22 , 23 , 24 , 25 , 26 ]. The great impact of the structure of the group linking two phosphine oxides on the complexation mode is worth noting.…”

Section: Introductionmentioning

confidence: 99%

Phosphineoxide-Chelated Europium(III) Nanoparticles for Ceftriaxone Detection

et al. 2023

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The present work demonstrates the optimization of the ligand structure in the series of bis(phosphine oxide) and β-ketophosphine oxide representatives for efficient coordination of Tb3+ and Eu3+ ions with the formation of the complexes exhibiting high Tb3+- and Eu3+-centered luminescence. The analysis of the stoichiometry and structure of the lanthanide complexes obtained using the XRD method reveals the great impact of the bridging group nature between two phosphine oxide moieties on the coordination mode of the ligands with Tb3+ and Eu3+ ions. The bridging imido-group facilitates the deprotonation of the imido- bis(phosphine oxide) ligand followed by the formation of tris-complexes. The spectral and PXRD analysis of the separated colloids indicates that the high stability of the tris-complexes provides their safe conversion into polystyrenesulfonate-stabilized colloids using the solvent exchange method. The red Eu3+-centered luminescence of the tris-complex exhibits the same specificity in the solutions and the colloids. The pronounced luminescent response on the antibiotic ceftriaxone allows for sensing the latter in aqueous solutions with an LOD value equal to 0.974 μM.

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Lanthanide Complexes (Ln=La, Nd, Dy) of Octaethyl propane‐1,1,3,3‐tetrayltetrakis(phosphonate): Multidentate Binding Competing with Monodentate DMSO Complexes

Koehne

Pietschnig

2022

Zeitschrift anorg allge chemie

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The preparation of lanthanide nitrate complexes [Ln(NO3)3{L}]n (Ln3+=La, Nd, Dy) supported by the octaethyl propane‐1,1,3,3‐tetrayltetrakis(phosphonate) (L) chelate ligand platform is presented. Re‐crystallization of these compounds from DMSO/THF led to a complete replacement of the multidentate phosphonate ester ligand and the formation of exclusively DMSO‐supported lanthanide nitrate species [Ln(NO3)3(DMSO)4]. The relative basicity of a model phosphonate ester vs. DMSO is explored with theoretical means, pointing out the relevance of solvation in this case in line with the experimentally observed exchange process. The optical properties of the dysprosium(III) derivatives are examined in the visible region indicating a significantly higher quantum yield for its tetraphosphonic ester complex than for the DMSO coordinated analog.

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Synthesis of Geminal Bis‐ and Tetrakisphosphonate Ester Derivatives and Their Coordination Behavior Towards Ca(II) Ions

Cited by 5 publications

References 63 publications

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides

Phosphineoxide-Chelated Europium(III) Nanoparticles for Ceftriaxone Detection

Lanthanide Complexes (Ln=La, Nd, Dy) of Octaethyl propane‐1,1,3,3‐tetrayltetrakis(phosphonate): Multidentate Binding Competing with Monodentate DMSO Complexes

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