Hexamethylhydrazinocyclotriphosphazene N3P3(NMeNH2)6: Starting reagent for the synthesis of multifunctionalized species, macrocycles, and small dendrimers

Kraemer, Raymond; Galliot, Christophe; Mitjaville, Joëlle; Caminade, Anne‐Marie; Majoral, Jean Pierre

doi:10.1002/(sici)1098-1071(199603)7:2<149::aid-hc8>3.0.co;2-8

Cited by 27 publications

(8 citation statements)

References 31 publications

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“…In parallel, three methyl hydrazine-terminated dendrimers were designed also from the hexachlorocyclotriphosphazene (PN) 3 Cl 6 . The smallest building block, the azidohexamethylhydrazinocyclotriphosphazene (denoted as 1 - NNH2 ), was accessed following the early described procedure , and obtained quantitatively in 88% yield (Scheme ). The preparation of 2 - NNH2 consists in nucleophilic substitution of the P(S)Cl 2 end groups of the “classical” phosphorus dendrimer D 1 with 4-(diphenylphosphino)phenol affording a dendrimer decorated with 12 diphenylphosphino groups.…”

Section: Resultsmentioning

confidence: 99%

Orthogonal Synthesis of Covalent Polydendrimer Frameworks by Fusing Classical and Onion-Peel Phosphorus-Based Dendritic Units

et al. 2016

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We report novel and new giant three-dimensional polymers having dendrimers as repeating units. The approach is illustrated here for macromolecular synthesis by polymeric condensation of well-defined single phosphorus dendrimers units. Specifically, classical and onion-peel phosphorus dendrimers, constructed by a divergent method from a cyclotriphosphazene core, were fused within the same tectonic nanostructure by several polymeric condensation approaches including hydrazine-to-aldehyde Schiff-base formation and amine-to-carboxylic acid peptide-like coupling. These reticular, easy to run metal-free routes afford a new library of hyperbranched macromolecular materials, featuring various phosphorus layers (both alternated and dissymmetrical), well-defined textured nanospheres, and controllable nanometric ordered substructures. The scope of the concept is successfully expanded to the integration of electro-redox viologen units resulting in the synthesis of new photoactive macromolecular materials.

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Section: Resultsmentioning

confidence: 99%

Orthogonal Synthesis of Covalent Polydendrimer Frameworks by Fusing Classical and Onion-Peel Phosphorus-Based Dendritic Units

et al. 2016

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“…9 In preliminary experiments, indications for the formation of sandwich complexes and hence cooperativity were found when hexamacrocycle II was reacted with potassium salts. 2…”

Section: Resultsmentioning

confidence: 99%

Complexation Studies of Phosphorus Containing Polymacrocyclic Compounds

Mouveaux

Levalois-Mitjaville

Jaeger

1999

Phosphorus Research Bulletin

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Phosphate and phosphazene derivatives of the type X=P(NMe-N=CH-B15C5)3 (X =0,5) and P3N3(NMe-N=CH-B15C5)6 containing three or six benzo 15-crown-5 cavities strongly chelate with cations and their efficiency and selectivity in binding cations are compared with those of unbounded crown ether. Using data obtained from evolution of 13C NMR spectra in CD3CN and distribution of picrate salts in a binary water-CHCl3 system show these new ligands to be excellent extracting agents.

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“…Cross-polarization magic-angle-spinning (CP/MAS) 13 C and 31 P NMR spectra were acquired on a Bruker Avance 400 WB spectrometer operating at 100 and 162 MHz, respectively. The compounds Ph 2 PC 6 H 4 OH, N 3 P(S)(NMeNH 2 ) 2 , G n x Cl, and N 3 P 3 (NMeNH 2 ) 6 were prepared according to literature procedures. Nitrogen sorption isotherms at 77 K were obtained with a Micromeritics ASAP 2010 apparatus.…”

Section: Methodsmentioning

confidence: 99%

Dendrimer for Templating the Growth of Porous Catechol-Coordinated Titanium Dioxide Frameworks: Toward Hemocompatible Nanomaterials

Katir

Marcotte

Michlewska

et al. 2019

ACS Appl. Nano Mater.

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Phosphorus dendrimers and nanosized metal oxide clusters are two dissimilar nanomaterials with promising applications in nanomedicine. Although outstanding holistic properties can be reached by the combination of organic and inorganic phases, few investigations were strikingly undertaken to associate these building blocks in a single nanostructured, open-framework hybrid material. With this aim, we designed herein five novel different generations of catechol-terminated phosphorus dendrimers (DG n : n = 1−5) and used them as structure-directing agents for titanium alkoxide mineralization. The covalent bonding occurring between peripheral catechols and soluble titanium oxo species and their further sol−gel cocondensation afford bimodal micromesoporous catechol-coordinated titanium dioxide nanomaterials. Their interplay with cells was assessed with a special emphasis on their hemolytic activity and cytotoxicity. Interestingly, enhanced biocompatibility was observed for these materials compared to their hybrid analogues built from ammonium-and phosphonate-terminated phosphorus dendrimers. These results demonstrate the importance of catechol-terminated groups both for bridging titanium dioxide clusters and for improving the materials' compatibility. Overall, this study sheds light on the importance of tuning the surface-interface hybrid composition and provides a blueprint for the rational design of bloodcompatible and drug-transporter materials.

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Hexamethylhydrazinocyclotriphosphazene N3P3(NMeNH2)6: Starting reagent for the synthesis of multifunctionalized species, macrocycles, and small dendrimers

Cited by 27 publications

References 31 publications

Orthogonal Synthesis of Covalent Polydendrimer Frameworks by Fusing Classical and Onion-Peel Phosphorus-Based Dendritic Units

Orthogonal Synthesis of Covalent Polydendrimer Frameworks by Fusing Classical and Onion-Peel Phosphorus-Based Dendritic Units

Complexation Studies of Phosphorus Containing Polymacrocyclic Compounds

Dendrimer for Templating the Growth of Porous Catechol-Coordinated Titanium Dioxide Frameworks: Toward Hemocompatible Nanomaterials

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