Facile Synthesis of Amine-Terminated Aromatic Polyamide Dendrimers via a Divergent Method

Washio, Isao; Shibasaki, and Yuji; Ueda, Mitsuru

doi:10.1021/ol0702425

Cited by 27 publications

(15 citation statements)

References 33 publications

(23 reference statements)

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“…27 The AB 2 building block was prepared via the reaction of 3,5-diaminobenzoic acid with trifluoroacetic anhydride and obtained in 89% yield after recrystallization from acetonitrile. 35 The G1 dendrimer was synthesized as shown in Scheme 1. The AB 2 building block was converted into acid chloride (AB 2 -Cl) by refluxing in thionyl chloride.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and properties of aromatic polyamide dendrimers with polyhedral oligomeric silsesquioxane cores

et al. 2015

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Aromatic polyamide dendrimers possessing polyhedral oligomeric silsesquioxane (POSS) cores were synthesized up to the sixth generation. Octa(n-propylamine)-POSS and 3,5-bis(trifluoroacetamido)benzoic acid were prepared as an eight-functional core and an AB 2 building block, respectively. Condensation of the core with the AB 2 building block, followed by deprotection via transamidation with hydrazine, was conducted to provide the G1 dendrimer. The other dendrimers up to the sixth generation were prepared in a similar manner. All dendrimers were obtained in high yields (>90%) via a simple precipitation process without the need for tedious purification steps such as column chromatography. The structures of the dendrimers were characterized by NMR, FT-IR, MALDI-TOF mass spectroscopy, and light scattering measurements. The dynamic light scattering and AFM measurements suggest that the dendrimers have squashed shapes on the substrate even for the sixth generation. The trifluoroacetamide-terminated dendrimers show specific fluorescence emission at 445 nm under 330 nm irradiation and the emission intensity is increased with increasing the generation number. The generation dependence of the emission intensity is similar to that of the intrinsic viscosity of the dendrimers.

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Section: Resultsmentioning

confidence: 99%

Synthesis and properties of aromatic polyamide dendrimers with polyhedral oligomeric silsesquioxane cores

et al. 2015

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“…A series of bidendron aramide dendrimers were chosen as target compounds ( Figure 1 ). [ 15 ] Since the repeating unit has all substitutes in the m -position, the aramide dendrimers are good mimics to the polyamide networks used in commercial membranes, but with a perfectly defi ned molecular structure. p-Phenylenediamine (PDA) as the core structural unit reduces the steric hindrance between the two dendritic segments.…”

Section: Uv-visible Spectroscopy To Monitor the Infl Uence Of Dendrimmentioning

confidence: 99%

“…The synthesis of aramide dendrimers G1-G3 followed a facile divergent approach recently reported by Ueda and coworkers ( Scheme 1 ). [ 15 ] Amine-terminated NH 2 -Gn (n = 1-3) were synthesized by using 3,5-bis(trifl uoroacetamido)benzoyl chloride as an AB 2 building block with all reactions carried out in a single fl ask. 2-[2-(2-Methoxyethoxy)ethoxy]acetyl chloride, which was…”

Section: Synthesis and Characterization Of Aramide Dendrimersmentioning

confidence: 99%

Nanofiltration Membranes with Modified Active Layer Using Aromatic Polyamide Dendrimers

Gao

Jubera

Mariñas

et al. 2012

Adv Funct Materials

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The modification of a commercial nanofiltration (NF) membrane (TFC‐S) with shape‐persistent dendritic molecules is reported. Amphiphilic aromatic polyamide dendrimers (G1–G3) are synthesized via a divergent approach and used for membrane active layer modification by direct percolation. The permeate samples collected from the percolation experiments are analyzed by UV‐visible spectroscopy to monitor the influence of dendrimer generations on percolation behavior and active layer modification. Further characterization of modified membranes by Rutherford backscattering spectrometry and atomic force microscopy techniques reveals a relatively low‐level accumulation of dendrimers inside the original TFC‐S NF membrane active layer and subsequent formation of a coating of pure aramide dendrimers on top of the active layer. A PES‐PVA ultrafiltration membrane is used as a control membrane support (without an NF active layer) showing that structural compatibility between the dendrimers and support plays an important role in the membrane modification process. The performance of the modified TFC‐S membrane is evaluated on the basis of the rejection abilities for a variety of water contaminants having a range of molecular size and chemistry. As the water flux is inversely proportional to the thickness of the active layer, the amount of dendrimers deposited for specific contaminants are optimized to improve the solute rejection while maintaining high water flux.

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“…Since the pioneering works of Vö gtle and Tomalia about three decades back, large numbers of synthetic strategies have been introduced for preparing dendrimers with different structural scaffolds [6][7][8][9]. Recent research focuses more on effective ways of tuning the properties of dendrimers for practical applications [10,11].…”

Section: Introductionmentioning

confidence: 99%

Effect of solvent-controlled aggregation on the intrinsic emission properties of PAMAM dendrimers

Jasmine

Kavitha

Prasad

2009

Journal of Luminescence

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Facile Synthesis of Amine-Terminated Aromatic Polyamide Dendrimers via a Divergent Method

Cited by 27 publications

References 33 publications

Synthesis and properties of aromatic polyamide dendrimers with polyhedral oligomeric silsesquioxane cores

Synthesis and properties of aromatic polyamide dendrimers with polyhedral oligomeric silsesquioxane cores

Nanofiltration Membranes with Modified Active Layer Using Aromatic Polyamide Dendrimers

Effect of solvent-controlled aggregation on the intrinsic emission properties of PAMAM dendrimers

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