Decorating step-by-step and independently the surface and the core of dendrons

An efficient system for the catalytic redox isomerization of the allylic alcohol 1-octen-3-ol to 3-octanone is presented. The homogeneous ruthenium(II) catalyst contains a monodentate phosphane ligand with a ferrocene moiety in the backbone and provides 3-octanone in quantitative yields. The activity is increased by nearly 90 % with respect to the corresponding triphenyl phosphane ruthenium(II) complex. By grafting the catalyst at the surface of a dendrimer, the catalytic activity is further increased. By introducing different spacers between ferrocene and phosphorus, the influence on the electronic properties of the complexes is shown by evaluating the electrochemical behavior of the compounds.

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“…Similar reaction conditions were applied for the synthesis of the dendritic ferrocenyl phosphane complexes 12…”

Section: Resultsmentioning

confidence: 99%

Ruthenium Complexes with Dendritic Ferrocenyl Phosphanes: Synthesis, Characterization, and Application in the Catalytic Redox Isomerization of Allylic Alcohols

Neumann

Dib

Sournia‐Saquet

et al. 2015

Chemistry A European J

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“…They comprise several ferrocene derivatives functionalized in most cases with a phosphine, eventually linked to the cyclopentadienyl ring through a spacer . Many functionalized phenols have been prepared from tyramine;, this includes functions having biological properties such as azabisphosphonic acid salts, of different types, diverse amino phosphonates, azabis carboxylate and azabis sulfonate salts, several mannose derivatives, ethacrynic acid, diverse phosphines such as an azabisphosphine, a thiazolylphosphine, and an iminophosphine, diverse fluorophores such as a maleimide, and a derivative of rhodamine . Other functionalized phenols comprise ligands for catalysis, such as phosphine, and diphosphine, iminophosphine, aminophosphine, diketone, pyridineimine, terpyridine, bisoxazoline, prolinol derivative, and cinchonine, diverse other compounds, such as aminophosphoniums, thioesters and thioamides, two types of ethacrynic derivatives,, long chains of type alkyl or perfluoroalkyl, or PEG (polyethyleneglycol), and fluorescent groups based on stilbazole or fluorene derivatives , .…”

Section: Synthesis Of Phosphorhydrazone Dendrimers and Dendronsmentioning

confidence: 99%

Phosphorhydrazones as Useful Building Blocks for Special Architectures: Macrocycles and Dendrimers

Majoral

Caminade

2018

Eur J Inorg Chem

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The role of phosphorhydrazide derivatives, in particular of type RP(X)(NMeNH 2 ) 2 for the synthesis of macrocycles and of type Cl 2 P(X)NMeNH 2 (X = O, S in both cases) for the synthesis of dendrimers, will be shown in this review. In both cases, condensation reactions with different types of aldehydes [a] Scheme 1. The first macrocycles obtained by condensation of two equiv. of phosphodihydrazides with two equiv. of dialdehydes.1460 Scheme 5. First example of a spherand based on phosphorhydrazides.Scheme 6. Phosphotrihydrazides for the synthesis of cryptands and macrocyclic polymers. 1461 Scheme 8. Two ways for the functionalization of N 3 P 3 Cl 6 with two functions in a 1:5 or 5:1 ratio. In the bottom, two cyclotriphosphazenes associated by fluorescent diphenols.Thanks are due to the CNRS, to the ANR 2017 SLOW2 for financial support, and to the GDR Phosphore.

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“…As it is not trivial to have a function at the core which will not react during the synthetic process, but which can be activated later, many studies have been carried out with the aim of exploring the diverse possibilities. The functions linked to the core and compatible with the growing of the dendrons were an allyl, a pyridine, an alkyl chloride or azide [45], a diethylphosphonate [46], a polyethyleneglycol (PEG) derivative [47], a phenol protected by a methyl ester, which can be deprotected [48], and an activated vinyl group able to react with various primary and secondary amines [49], compatible with phosphine surface groups [50]. The thermal stability of several dendrons of various generations with the activated vinyl group as core and diverse types of terminal functions (aldehyde, tertiary amine, nitrile) was measured.…”

Section: Dendrons (Type C)mentioning

confidence: 99%

“…The same family of dendrons, but having Boc-protected amines as terminal groups, were also synthesized recently [33]. a polyethyleneglycol (PEG) derivative [47], a phenol protected by a methyl ester, which can be deprotected [48], and an activated vinyl group able to react with various primary and secondary amines [49], compatible with phosphine surface groups [50]. The thermal stability of several dendrons of various generations with the activated vinyl group as core and diverse types of terminal functions (aldehyde, tertiary amine, nitrile) was measured.…”

Section: Dendrons (Type C)mentioning

confidence: 99%

Bifunctional Phosphorus Dendrimers and Their Properties

Caminade

Majoral

2016

Molecules

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Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. This review will discuss the case of bifunctional phosphorus-containing dendrimers, and the consequences for their properties. Besides the terminal functions, dendritic structures may have also a function at the core, or linked off-center to the core, or at the core of dendrons (dendritic wedges). Association of two dendrons having different terminal functions leads to Janus dendrimers (two faces). The internal structure can also possess functional groups on one layer, or linked to one layer, or on several layers. Finally, there are several ways to have two types of terminal functions, besides the case of Janus dendrimers: either each terminal function bears two functions sequentially, or two different functions are linked to each terminal branching point. Examples of each type of structure will be given in this review, as well as practical uses of such sophisticated structures in the fields of fluorescence, catalysis, nanomaterials and biology.

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Decorating step-by-step and independently the surface and the core of dendrons

Cited by 19 publications

References 21 publications

Ruthenium Complexes with Dendritic Ferrocenyl Phosphanes: Synthesis, Characterization, and Application in the Catalytic Redox Isomerization of Allylic Alcohols

Ruthenium Complexes with Dendritic Ferrocenyl Phosphanes: Synthesis, Characterization, and Application in the Catalytic Redox Isomerization of Allylic Alcohols

Phosphorhydrazones as Useful Building Blocks for Special Architectures: Macrocycles and Dendrimers

Bifunctional Phosphorus Dendrimers and Their Properties

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