Phosphorylation of Dialkylaminomethylated Calix[4]-Resorcinarenes with Some P(III) and P(IV) Derivatives

Abstract

The phosphorylation of dialkylaminomethylated calix[4]resorcinarenes with P(m)-amides and P(TV)chlorides under various conditions results in the formation of different structures with phosphorus containing fragments fixed on the cavity rim. Hydrophosphoryl compounds based on dialkylaminomethylated calix[4]resorcinarenes have been synthesized and some of their properties investigated.     

Novel 4-chloro-or-4-bromoresorcinol-based bicyclic phosphonates

Abstract

The reaction of 4-chloro- and 4-bromoresorcinol with 2-ethoxyvinylphosphonic acid dichloroanhydride has been investigated for the first time. It has been determined that the product of the reaction is the mixture of structural isomers of bicyclic phosphonates at the ratio of 9:1. The structure and composition of the compounds have been elucidated from ¹H, ³¹P, and ¹³C NMR spectroscopy, mass-spectrometry (MALDI-TOF), as well as elemental and X-ray analysis.     

Phosphorylation of oxyethylated resorcinol and calix[4]resorcinarene with P(III) acid amides

Abstract

Phosphorylation of 1,3-bis(2-hydroxyethoxy)benzene and octa(2-hydroxyethyl) calix[4]-resorcinarenes with P(III) acid amides and chloramides has been studied. It has been determined that the nature of phosphorous acid amides affects significantly the synthetic result of the reaction.     

The Syntheses and Binding Properties of the Novel Organophosphorus Calixarenes

Phosphorylation of bromo, dialkylaminomethyl calix[4]resorcinarenes with various long chain aliphatic radicals with a number of P(III) derivatives i.e. triamido-and diamidophosphites, and polyhalogenides of P(III), P(IV) is described. A series of phosphoamide cavitands were obtained. Structures and properties of synthesized compounds were discussed on the basis of physical and quantum chemical methods.     

Novel Naphthol‐Based Bicyclic Phosphonates

Condensation of naphthol‐1 and naphthol‐2 with 2‐ethoxyvinyphosphonic acid dichloroanhydride in boiling toluene in the presence of trifluoroacetic acid has resulted in high yields of unknown bicyclic phosphonates. Composition and structure of the products obtained were confirmed according to ¹H and ³¹P nuclear magnetic resonance, infrared spectroscopy, and X‐ray analysis.     

Complex Formation of d‐Metal Ions at the Interface of TbIII‐Doped Silica Nanoparticles as a Basis of Substrate‐Responsive TbIII‐Centered Luminescence

The complex formation of d‐metal ions at the interface of Tb^III‐doped silica nanoparticles modified by amino groups is introduced as a route to sensing d‐metal ions and some organic molecules. Diverse modes of surface modification (covalent and noncovalent) are used to fix amino groups onto the silica surface. The interfacial binding of d‐metal ions and complexes is the reason for the Tb^III‐centered luminescence quenching. The regularities and mechanisms of quenching are estimated for the series of d‐metal ions and their complexes with chelating ligands. The obtained results reveal the interfacial binding of Cu^II ions as the basis of their quantitative determination in the concentration range 0.1–2.5 μM by means of steady‐state and time‐resolved fluorescence measurements. The variation of chelating ligands results in a significant effect on the quenching regularities due to diverse binding modes (inner or outer sphere) between amino groups at the interface of nanoparticles and Fe^III ions. The applicability of the steady‐state and time‐resolved fluorescence measurements to sense both Fe^III ions and catechols in aqueous solution by means of Tb^III‐doped silica nanoparticles is also introduced.     

An unusual reaction of 2‐ethoxyethenylphosphonic dichloride with resorcinol and its derivatives: Synthesis of bicyclic phosphonates with endocyclic P–C bond

The condensation of 2‐ethoxyethenyl‐ phosphonic dichloride with resorcinol and its derivatives in dichloromethane in the presence of trifluoroacetic acid results in the formation of new bicyclic phosphonates with an endocyclic P C bond. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 22:1–4, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20646     

Formation of phosphorus‐containing cage structures in the reaction of 2‐ethoxyvinylphosphonic acid dichloroanhydride with resorcinol and its derivatives

The scheme of formation of bicyclic phosphonates 3 synthesized on the basis of resorcinol and its derivatives was suggested based on the model reactions of dichloroanhydride 1 with 3‐methoxyphenol 7 in the presence of triethylamine with a variable ratio of reagents. Composition and structure of the products obtained were confirmed according to ¹H and ³¹P NMR, IR spectroscopy, elemental analysis, and X‐ray analysis. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:340–344, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21022