Convergent synthesis of dendrimers based on 1,3,3-trisubstituted 2-oxindoles

Vandendriessche, Annelies; Thomas, Joice; Oosterwijck, Chantall Van; Huybrechts, Jos; Dervaux, Bart; D'hollander, Stijn; Prez, Filip Du; Dehaen, Wim; Smet, Mario

doi:10.1016/j.eurpolymj.2009.08.001

Cited by 13 publications

(12 citation statements)

References 11 publications

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“…Finally, we would like to suggest that the process might be extended to sets of two or three different 1-aryl-2propyn-1-ones that should lead to unsymmetrically substituted 1,3,5-triaroylbenzenes, which are precursors of a number of interesting dendrimers. [18,19] Such reactions have been successfully performed in organic solvents with added amine catalysts. Furthermore, the phenyl ring of 1-phenyl-2propyn-1-one can include a protected propiolyl group as a substituent.…”

Section: Resultsmentioning

confidence: 99%

“…[12b, 18,19] Hyperbranched polymers with a high degree of branching, such as poly(aroxycarbonylphenylene)s and ferrocene-containing hyperbranched poly(aroylarylene)s have been prepared. [20a, b] The physicochemical properties of disc-like molecules of medium size thus warrants further investigation, and herein we report a synthetic study of 1,3,5-triaroylbenzene in pressurized hot water.…”

Section: Introductionmentioning

confidence: 99%

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One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

Tanaka

Nakamura

Iwado

et al. 2010

Chemistry A European J

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Cyclotrimerization of 1-phenyl-2-propyn-1-one in pressurized hot water gave 1,3,5-tribenzoylbenzene in one pot in 65 % yield after 7 min at 200 °C, or in 74 % yield after 60 min at 150 °C. The reaction did not take place in the absence of water, and added base promoted the reaction at 250 °C, suggesting a mechanism of three-consecutive Michael addition reactions. The reaction rates increased with temperature, but the yield of 1,3,5-tribenzoylbenzene decreased at the expense of formation of acetophenone as a side product at higher temperatures. p-Methyl and p-chloro-substituents on the phenyl ring retarded and enhanced the reaction, respectively. A mechanism involving the enol of benzoylacetaldehyde at a branching point of the pathway leading to 1,3,5-tribenzoylbenzene and acetophenone was suggested.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

Tanaka

Nakamura

Iwado

et al. 2010

Chemistry A European J

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“…Even though this synthesis have many advantages over the divergent process, this synthesis becomes very complex due to the generation's slow process of reaction. (Vandendriessche, 2009) Usually, Poly (aryl ether ) is the skeleton for the dendritic structure, which is synthesized by the convergent method (Pandita, 2014).…”

Section: Synthesis By Convergent Methodsmentioning

confidence: 99%

A Comprehensive review on Dendrimers in current advanced Drug delivery

Chirag¹,

Gowda²,

Babu³

et al. 2020

ijrps

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In this particular review, it is been noted that Dendrimers are novel three-dimensional globular nano-polymeric structure; having multiple functional groups on the surface enhances their function. Synonymous terms for dendrimer include arborols and cascade molecules. The importance of dendrimers in a large variety of fields has been detected, where the various types of dendrimers helps in various fields of drug delivery with the different types of dendrimers with the generation. Hence the dendrimer gains more attention from researchers among various nano-materials. Convenient synthesis of the structure makes them as a good nano-material for drug delivery. In recent, dendrimers showed their activity in different drug delivery systems having properties like cancer targeting, anti-bacterial, ocular drug delivery, etc.. The future direction about the dendrimers are been discussed. The present review is focused on types of dendrimers like Polypropylene Imine dendrimer (PPI), Poly(amidoamine) dendrimers (PAMAM), Poly-l-lysine dendrimers, Type of Frechet’s dendrimer, Core-shell tecto dendrimers, Chiral dendrimers, Liquid crystalline dendrimers, Peptide dendrimers, Multiple antigen peptide dendrimers, Glyco-dendrimers, Hybrid dendrimers, Polyester dendrimers in which among these type of dendrimers, the Polypropylene Imine dendrimer (PPI) and Poly(amidoamine) dendrimers are found to be good carriers for various targeting site, Dendrimers are synthesized through various methods like Divergent method, Convergent method, Hyper cores and branched monomer growth method, Double exponential growth method, Click chemistry method, recent advances in dendrimers are used in the Anti-cancer delivery, Anti-bacterial delivery, oral route delivery, pulmonary drug delivery, transdermal drug delivery, ocular delivery, and targeted drug delivery the safety aspects, and future strategies are also been discussed in the below article.

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“…Recently, the synthesis and characterization of model dendrimers made with the same building blocks in the same molecular mass domain as the hyperbranched poly(aryleneoxindole) had been reported, revealing that the deviation from the absolute M w values is rather small when using polystyrene standards. Significant deviations only start for larger molar masses (>12 000) . The linear analog of HPE, depicted as LPE ( M w of 18 600 and acid density of 4.4 H + mmol g –1 ) was synthesized through the polycondensation reaction of the A 2 and the B 2 monomer, isatin, and 1,4‐phenylenebis((4‐phenoxyphenyl)methanone), respectively, under acidic conditions (Figure ) .…”

Section: Methodsmentioning

confidence: 99%

“…The remaining sodium hydroxide was removed by washing with water. The LbL coating was done using an automated dip coating machine (High Throughput Membrane Leuven, HTML, Belgium) . The automated dip coating machine consists of four separate vessels, as depicted in Figure S1 (Supporting Information): two for the polyelectrolyte solutions and two for rinsing purposes.…”

Section: Methodsmentioning

confidence: 99%

Ultrathin Single Bilayer Separation Membranes Based on Hyperbranched Sulfonated Poly(aryleneoxindole)

Joseph

Thomas

Ahmadiannamini

et al. 2017

Adv Funct Materials

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The layer‐by‐layer method is an attractive technique for the fabrication of ultrathin nanostructured polyelectrolyte multilayer membranes (PEMM). A simple two‐step procedure is described here for the preparation of an ultrathin, nanostructured membrane comprising a 5–7 nm thick selective layer, consisting only of one single bilayer of poly(diallyldimethylammoniumchloride) and hyperbranched sulfonated poly(aryleneoxindole). These single bilayered membranes exhibit an outstanding solvent‐resistant nanofiltration performance, which is superior to that of commercial membranes as well as to previously reported multilayer membranes having 10–20 bilayers. A comparative study between hyperbranched polyelectrolyte (HPE) and linear polyelectrolyte supports the role of the specific 3D structure of the hyperbranched polyelectrolyte in these excellent separation properties. The work thus encompasses the use of HPEs as an ideal choice for PEMMs, which opens up a new route to significantly decrease the overall membrane preparation time while realizing excellent filtration properties.

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Convergent synthesis of dendrimers based on 1,3,3-trisubstituted 2-oxindoles

Cited by 13 publications

References 11 publications

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

A Comprehensive review on Dendrimers in current advanced Drug delivery

Ultrathin Single Bilayer Separation Membranes Based on Hyperbranched Sulfonated Poly(aryleneoxindole)

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