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[ CAS No. 33527-91-2 ] {[proInfo.proName]}

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Chemical Structure| 33527-91-2
Chemical Structure| 33527-91-2
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Coskun, Halil Ibrahim ; De Luca Bossa, Ferdinando ; Hu, Xiaolei , et al. DOI: PubMed ID:

Abstract: In atom transfer radical polymerization (ATRP), dormant alkyl halides are intermittently activated to form growing radicals in the presence of a CuI/L/X-CuII/L (activator/ deactivator) catalytic system. Recently developed very active copper complexes could decrease the catalyst concentration to ppm level. However, unavoidable radical termination results in irreversible oxidation of the activator to the deactivator species, leading to limited monomer conversions. Therefore, successful ATRP at a low catalyst loading requires continuous regeneration of the activators. Such a regenerative ATRP can be performed with various reducing agents under milder reaction conditions and with catalyst concentrations diminished in comparison to conventional ATRP. Photoinduced ATRP (PhotoATRP) is one of the most efficient methods of activator regeneration. It initially employed UV irradiation to reduce the air-stable excited X-CuII/L deactivators to the activators in the presence of sacrificial electron donors. Photocatalysts (PCs) can be excited after absorbing light at longer wavelengths and, due to their favorable redox potentials, can reduce X-CuII/L to CuI/L. Herein, we present the application of three commercially available xanthene dyes as ATRP PCs: (RB), (RD), and (RD-6G). Even at very low Cu catalyst concentrations (50 ppm), they successfully controlled PhotoATRP. Well-defined polymers with preserved livingness were prepared under green LED irradiation, with subppm concentrations ([PC] ≥ 10 ppb) of and or 5 ppm of . Interestingly, these PCs efficiently controlled ATRP at wavelengths longer than their absorption maxima but required higher loadings. Polymerizations proceeded with high initiation efficiencies, yielding polymers with narrow molecular weight distributions and high chain-end fidelity. UV?vis, fluorescence, and laser flash photolysis studies helped to elucidate the mechanism of the processes involved in the dual-catalytic systems, comprising parts per million of Cu complexes and parts per billion of PCs.

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Piotr Mocny ; Ting-Chih Lin ; Rohan Parekh , et al. DOI:

Abstract: (PVDF) shows excellent chemical and thermal resistance and displays high dielectric strength and unique piezoelectricity, which are enabling for applications in membranes, electric insulators, sensors, or power generators. However, its low polarity and lack of functional groups limit wider applications. While inert, PVDF has been modified by grafting polymer chains by atom transfer radical polymerization (ATRP), albeit via an unclear mechanism, given the strong C–F bonds. Herein, we applied and green-light-mediated ATRP to modify PVDF-based materials. The method gave nearly quantitative (meth)acrylate monomer conversions within 2 h without deoxygenation and without the formation of unattached homopolymers, as confirmed by control experiments and DOSY NMR measurements. The gamma distribution model that accounts for broadly dispersed polymers in DOSY experiments was essential and serves as a powerful tool for the analysis of PVDF. The NMR analysis of poly(methyl acrylate) graft chain-ends on PVDF-CTFE (statistical copolymer with chlorotrifluoroethylene) was carried out successfully for the first time and showed up to 23 grafts per PVDF-CTFE chain. The grafting density was tunable depending on the solvent composition and light intensity during the grafting. The initiation proceeded either from the C–Cl sites of PVDF-CTFE or via unsaturations in the PVDF backbones. The dehydrofluorinated PVDF was 20 times more active than saturated PVDF during the grafting. The method was successfully applied to modify PVDF, PVDF-HFP, and Viton A401C. The obtained PVDF-CTFE-g-PnBMA materials were investigated in more detail. They featured slightly lower crystallinity than PVDF-CTFE (12–18 vs 24.3%) and had greatly improved mechanical performance: Young’s moduli of up to 488 MPa, ductility of 316%, and toughness of 46 × 10[6] J/m3.

Keywords: poly(vinylidene fluoride) ; fluoropolymers ; ATRP ; photopolymerization ; grafting ; DOSY NMR ; stretchability ; toughness

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Bokouende, Sergely Steephen ; Ward, Cassandra L ; Allen, Matthew J DOI: PubMed ID:

Abstract: Ligands play a crucial role in supporting or stabilizing the divalent oxidation state of lanthanide metals. To expand the range of ligands used to chelate divalent lanthanide ions, we synthesized and studied the structural and photophysical properties of complexes of EuII and SmII with hexamethylhexacyclen, , , and as supporting ligands. Coordination of hexamethylhexacyclen, an analogue of , generates sterically crowded complexes of EuII and SmII that are either seven or eight coordinate and adopt a range of geometries that differ from those of their 18- crown-6 counterparts and from those of lanthanide-containing complexes with the acyclic tetradente tertiary amine ligands included in this report. The emission spectra of EuII(hexamethylhexacyclen) show a moderate sensitivity to counterion identity and are more red-shifted compared to those of complexes of EuII with and the hexamethylated aza derivative of 2.2.2-cryptand. In addition, the morphology of hexamethylhexacyclen in [LnI- (hexamethylhexacyclen)]I was found to resemble that of thermally stable alkalides of the form [M(hexamethylhexacyclen)]Na? (M = K+ or Cs+), suggesting that hexamethylhexacyclen could be an interesting ligand for strongly reducing lanthanide ions.

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Coskun, Halil Ibrahim ; Votruba-Drzal, Thomas ; Wu, Hanshu , et al. DOI:

Abstract: The photoATRP of methyl acrylate (MA) is investigated using ribo?avin (RF)and CuBr2 /Me6 TREN as a dual catalyst system under green LED irradiation(λ ≈ 525 nm). Both RF and CuBr2 /Me6 TREN enhanced oxygen tolerance,enabling e?ective ATRP in the presence of residual oxygen. High molar masspolymers (up to Mn ≈ 129 000 g·mol?1) with low dispersity (D ≤ 1.16) areprepared, and chain-end ?delity is con?rmed through successful chainextension. The molecular masses of the obtained polymer increased linearlywith conversion and showed high initiation e?ciency. Mechanistic studies bylaser ?ash photolysis reveal that the predominant activator generationmechanism is reductive quenching of RF by Me6 TREN (83%, under[CuBr2]/[Me6 TREN] = 1/3 condition), supported by polymerization kineticsand thermodynamic calculations.

Keywords: ATRP ; photocatalyst ; photopolymerization ; riboflavin

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Product Details of [ 33527-91-2 ]

CAS No. :33527-91-2 MDL No. :MFCD00015607
Formula : C12H30N4 Boiling Point : -
Linear Structure Formula :((CH3)2NCH2CH2)3N InChI Key :VMGSQCIDWAUGLQ-UHFFFAOYSA-N
M.W : 230.39 Pubchem ID :263094
Synonyms :

Calculated chemistry of [ 33527-91-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 9
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.38
TPSA : 12.96 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.59
Log Po/w (XLOGP3) : 0.38
Log Po/w (WLOGP) : -0.03
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : -0.21
Consensus Log Po/w : 0.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.91
Solubility : 28.1 mg/ml ; 0.122 mol/l
Class : Very soluble
Log S (Ali) : -0.22
Solubility : 140.0 mg/ml ; 0.606 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.99
Solubility : 2.38 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.06

Safety of [ 33527-91-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:
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