Pmdeta

Manufactured by Merck Group

Sourced in Germany, United States

PMDETA is a chemical compound used as a reagent and complexing agent in various laboratory applications. It functions as a chelating agent, forming stable complexes with metal ions. The core purpose of PMDETA is to facilitate various chemical reactions and processes that require the coordination of metal species.

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Close spelling variants of this product

N,N,N′,N′,N″-Pentamethyl diethylenetriamine (PMDETA, (13 citations)

32 protocols using pmdeta

Synthesis of Polymer-Grafted Surfaces

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Iron (II) stearate (Strem Chemicals, Bischheim, France, 9% Fe), ethanol, acetone, and hexane from Alfa Aesar were used without purification. Octyl ether (Sigma-Aldrich, Saint-Quentin-Fallavier, France, 99%) and oleic acid (90%, Alfa Aesar, Kandel, Germany) were distilled under reduced pressure. The purity of Octyl ether was controlled by gas chromatography. Toluene (Carlo Erba, Val de Reuil, France, 99.9%) and anhydrous THF (Carlo Erba, Val de Reuil, France, 99.9%) were refluxed and distilled over sodium and sodium/benzophenone, respectively. Copper (I) bromide (Sigma-Aldrich, Saint-Quentin-Fallavier, France, 98%), N,N,N′N″,N″-pentamethyldiethylenetriamine (PMDETA, Sigma-Aldrich, Saint-Quentin-Fallavier, France, 99%), ethyl-2-bromoisobutyrate (Alfa Aesar, Kandel, Germany, 98%), and Anisole (Sigma-Aldrich, Saint-Quentin-Fallavier, France, 99%) were used without purification. Styrene (Sigma-Aldrich, Saint-Quentin-Fallavier, France, 99%) was distilled over sodium under reduced pressure. Methyl methacrylate (Acros Organics, Geel, Belgium) was purified by column chromatography on basic aluminum oxide (Sigma-Aldrich, Saint-Quentin-Fallavier, France). 11-Phosphonoundecyl 2-bromo-2-methyl-propionate (M_W = 401.28 g/mol) as an ATRP initiator with a C₁₁ spacer was synthetized in the laboratory, following the experimental method reported by Maliakal et al. [18 (link)].

Vergnat V., Heinrich B., Rawiso M., Muller R., Pourroy G, & Masson P. (2021). Iron Oxide/Polymer Core–Shell Nanomaterials with Star-like Behavior. Nanomaterials, 11(9), 2453.

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Purification of Monomers and Catalysts for ATRP Synthesis

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All chemicals were stored in an argon-filled glovebox after purification and before use. Styrene (99%, stabilized, Acros Organics) and oligo-oxyethylene methyl ether methacrylate (OEM, > 99%, stabilized, Sigma-Aldrich, average molar mass = 500 g mol⁻¹) were purified by passage through a basic alumina column. The Styrene was dried further by distilling it from calcium hydride. OEM and Styrene were degassed via three freeze–pump–thaw cycles. Copper bromide [Cu(I)Br, 98%, Acros Organics] was purified by stirring in acetic acid for 30 min, filtering, washing twice with cold ethanol, and drying under dynamic vacuum. Anhydrous methanol (99.8%, Sigma-Aldrich) was stirred with calcium hydride, degassed via three freeze–pump–thaw cycles, and distilled. Ethyl 2-bromoisobutyrate (EBiB, 98%, Sigma-Aldrich), N,N,N′,N″,N″′-pentamethyldiethylenetriamine (PMDETA, 99%, Sigma-Aldrich), and anisole (>99%, Fisher Scientific) were degassed via three freeze–pump–thaw cycles. Dry tetrahydrofuran (THF, >99%, optima, Fisher-Scientific) was degassed by purging with argon and dried on solvent purification columns. Lithium triflate (99.995%, Sigma-Aldrich) was dried at 150 °C for 48 h.

Morris M.A., Sung S.H., Ketkar P.M., Dura J.A., Nieuwendaal R.C, & Epps TH I.I.I. (2019). Enhanced Conductivity via Homopolymer-Rich Pathways in Block Polymer-Blended Electrolytes. Macromolecules, 52(24), https://doi.org/10.1021/acs.macromol.9b01879.

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Synthesis of Star Polymer Carrier (SPc)

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SPc was synthesized following a previously described method [12 (link)]. Briefly, the star initiator Pt-Br is constructed by adding 2-bromo-2-methylpropionyl bromide (HEOWNS) dropwise into the pentaerythritol (Alfa Aesar) solution in dry tetrahydrofuran and triethylamine (Beijing Chemical Works). The initiator Pt-Br was further polymerized with DMAEMA (Energy Chemical) under a nitrogen atmosphere with the help of tetrahydrofuran, PMDETA (Sigma-Aldrich) and CuBr (Sigma-Aldrich). Dialysis was carried out to purify the crude product and SPc was obtained as white powder after being freeze-dried. A 60 g/L stock of SPc was prepared with double distilled water (ddH₂O). To synthesize fluorescent SPc, TPE-pentaerythritol was used instead of pentaerythritol to prepare the TPE-4Br star initiator and the subsequent steps were the same.

Yan S., Li N., Guo Y., Chen Y., Ji C., Yin M., Shen J, & Zhang J. (2022). Chronic exposure to the star polycation (SPc) nanocarrier in the larval stage adversely impairs life history traits in Drosophila melanogaster. Journal of Nanobiotechnology, 20, 515.

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Synthesis of PEG-based Multicomponent Conjugates

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Prepared bPEI-azide (MW = 2300) 100 mg along with 220 mg of mPEG-alkyne (MW = 5,000, Creative PEGWorks) and 550 mg of PEBP-alkyne (MW = 6300) were dissolved in 10 mL DMF and degassed by N₂ for 30 min. Next, 6 mg CuBr (Sigma-Aldrich) and 10 mg N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA, Sigma-Aldrich) were quickly added in a sealed environment under N₂ protection to initiate the click reaction (Fig. 2). After stirring overnight, a 20 kDa MW dialysis membrane (Spectra/Por) was used to remove unreacted materials with the dialysate replaced five times. The freeze–dried powder was characterized by ¹H NMR in CDCl₃ solution and stored at −20 °C.

Fan J., He Q., Jin Z., Chen W, & Huang W. (2018). A novel phosphoester-based cationic co-polymer nanocarrier delivers chimeric antigen receptor plasmid and exhibits anti-tumor effect. RSC Advances, 8(27), 14975-14982.

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Anionic Polymerization of Fluorinated Acrylates

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Anisole (Sigma-Aldrich)
was vacuum distilled over sodium. CuBr (Sigma-Aldrich) was extracted
with glacial acetic acid and then washed with diethyl ether, dried,
and stored under nitrogen. N,N,N′,N″,N‴-Pentamethyldiethylenetriamine
(PMDETA, Sigma-Aldrich) and ethyl α-bromophenylacetate (EBPA)
were freshly distilled before use. Perfluorohexylethyl acrylate (FA,
Fluorochem) and PEGMA (M_n = 300 g mol^–1, DP_n ≈ 5, D̵ = 1.2, Sigma-Aldrich) were filtered on basic alumina to remove inhibitors.

Delledonne A., Guazzelli E., Pescina S., Bianchera A., Galli G., Martinelli E, & Sissa C. (2023). Amphiphilic Fluorinated Unimer Micelles as Nanocarriers of Fluorescent Probes for Bioimaging. ACS Applied Nano Materials, 6(17), 15551-15562.

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Synthesis of Polymer Brushes via SI-ATRP

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Acetonitrile (ACN, VWR), 3-aminopropyldimethylethoxysilane (APDMES) (abcr, 97%),

α

-bromoisobutyryl bromide (BIBB) (Sigma Aldrich, 98%), CuBr₂ (Sigma-Aldrich, >99.9%), CuBr (Sigma-Aldrich, >99.9%), dichlormethane (DCM) (VWR), 4-(dimethylamino)-pyridin (DMAP) (Sigma Aldrich), ethanol (Sigma Aldrich), hydrogen peroxide (Carl Roth, 30%), N,N,N′,N′′,N′′′-pentamethyldiethylenetriamine (PMDETA) (Sigma Aldrich, 99%), styrene (Sigma Aldrich, 99%), methyl methacrylate (MMA) (Sigma Aldrich, 99%), water, methanol (Sigma Aldrich), sodium ascorbate (Sigma Aldrich), sulfuric acid (Fischer chemicals, 95%), triethylamine (TEA) (Sigma Aldrich, 99%), inhibitor remover resin (Alfa Aesar), aluminum oxide active basic (Sigma Aldrich). All compounds were used without further purification. To remove the inhibitor hydroquinone monomethyl ether (MEHQ) from MMA and 4-tert-butylcatechol from styrene, MMA was stirred with inhibitor remover resin for 30 min and styrene was passed through a basic aluminum oxide packed column. Silicon substrates were purchased from Active Business Company GmbH Brunnthal Germany.

Hildebrandt M., Shin E.Y., Yang S., Ali W., Altinpinar S, & Gutmann J.S. (2020). Investigation of Roughness Correlation in Polymer Brushes via X-ray Scattering. Polymers, 12(9), 2101.

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Purification of Monomers and Catalysts for Polymerization

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Butyl acrylate (TCI, 99%), methyl methacrylate (DAEJUNG CHEMICALS & METALS, Siheung, Korea 99.5%), and styrene (Junsei, Tokyo, Japan, 99.5%) were purified by passing through a basic alumina column before use. Copper(I) bromide (CuBr, Sigma-Aldrich, Seoul, Korea, 98.0%) and copper(I) chloride (CuCl, Sigma-Aldrich, 98.0%) were purified by stirring with glacial acetic acid, followed by filtering and washing the resulting solid four times with ethanol. The solid was dried under a vacuum for two days. Anisole (DAEJUNG CHEMICALS & METALS, 98.0%), (1-Bromoethyl)benzene (Sigma-Aldrich, 98%), copper(II) bromide (CuBr2, Sigma-Aldrich, 98.0%), copper(II) chloride (CuCl2, Sigma-Aldrich, 98.0%) and N,N,N

^{'}

^{″}

^{″}

-pentamethyldiethylenetriamine (PMDETA, Sigma-Aldrich, 98%), and all other chemicals, internal standards, and solvents were used as received.

Lee S.I., Seo M.G., Huh J, & Paik H.J. (2022). Small-Angle X-ray Scattering Analysis on the Estimation of Interaction Parameter of Poly(n-butyl acrylate)-b-poly(methyl methacrylate). Polymers, 14(24), 5567.

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Synthesis of Combretastatin A-4 Derivative

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Polyethyleneglycol methyl ether methacrylate (PEGMA, M_n = 300 g/mol, average degree of polymerization ≈5) (Sigma-Aldrich, Darmstadt, Germany), triethyleneglycol methyl ether methacrylate (TEGMA M_n = 232 g/mol) (Sigma-Aldrich, Darmstadt, Germany), and perfluorohexylethyl acrylate (FA, Fluorochem, Hadfield, United Kingdom) were passed through basic alumina to remove inhibitors. N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA, Sigma-Aldrich) and ethyl α-bromophenylacetate (EBPA, Sigma-Aldrich, Darmstadt, Germany) were distilled under vacuum. CuBr₂ (Sigma-Aldrich, Darmstadt, Germany) was recrystallized from water solution. Toluene (Sigma-Aldrich, Darmstadt, Germany) was distilled at atmospheric pressure after reflux over calcium hydride. 3-Hydroxyanisaldehyde, 3,4,5-trimethoxyphenylacetic acid, acetic anhydride, triethyl amine, and copper (powder) were used as received (Sigma-Aldrich, Darmstadt, Germany). Quinoline was distilled under reduced pressure before use.
The preparation of the cis-Combretastatin A-4 (CA-4) was carried out following a two-step literature procedure, obtaining the desired product with a 98% GLC purity and a 40% yield [61 (link)].
Common laboratory solvents and other reagents (Sigma-Aldrich, Darmstadt, Germany) were used as received.

Calosi M., Guazzelli E., Braccini S., Lessi M., Bellina F., Galli G, & Martinelli E. (2022). Self-Assembled Amphiphilic Fluorinated Random Copolymers for the Encapsulation and Release of the Hydrophobic Combretastatin A-4 Drug. Polymers, 14(4), 774.

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Synthesis of Clickable Polymer Conjugates

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Poly(ε-caprolactone) diol (CAPA^® 2402, molar mass 4000 g mol⁻¹, Solvay Chemicals Inc., Houston, TX, USA) and methoxy poly(ethylene glycol) (molar mass 5000 g mol⁻¹, Sigma-Aldrich) were precipitated in cold methanol (−30 °C), filtered, and dried under vacuum at 40 °C overnight. Tert-butyl acrylate (tBA, Sigma-Aldrich, Darmstadt, Germany) was passed through a column of alumina to remove the inhibitor. Copper (I) bromide (CuBr, Sigma-Aldrich, Darmstadt, Germany), pentamethyldiethylenetriamine (PMDETA, Sigma-Aldrich), α-bromoisobutyryl bromide (Sigma-Aldrich), triethylamine (Fluka, Fisher Scientific, Loughborough, UK), 4-pentynoic acid (Acros, through Labimex, Sofia, Bulgaria), sodium azide (NaN₃, Fluka), 4-dimethylaminopyridine (Sigma-Aldrich), N-(3-dimethylaminopropyl)-Nʹ-ethylcarbodiimide hydrochloride (EDC, Merck), CAPE (synthetic procedure described in [24 (link)]), N-hydroxysulfosuccinimide sodium salt (Sulfo-NHS, Sigma-Aldrich), DMF (Sigma-Aldrich), tetrahydrofuran (Sigma-Aldrich) Triton X-105 (Sigma-Aldrich), cystamine dichloride (Merk, Sofia, Bulgaria), dithiothreitol (Sigma-Aldrich), and ethanol (Acros) were used as received.

Kamenova K., Grancharov G., Kortenova V, & Petrov P.D. (2022). Redox-Responsive Crosslinked Mixed Micelles for Controllable Release of Caffeic Acid Phenethyl Ester. Pharmaceutics, 14(3), 679.

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Synthesis and Characterization of Functional Monomers

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N-Isopropylacrylamide (NIPAAm, 99%, Acros) was purified by recrystallization in n-hexane for three times prior to use. The monosaccharide monomer (Glc), tetra-acetylated monosaccharide monomer (AcGlc), trifluoromethyl phenylthiourea monomer (PT), and various tripeptides were synthesized (see Supplementary information for details). Toluene, dichloromethane, methanol, and pyridine were distilled and dried before use according to standard procedures. Cu(I)Br (99.998%, Alfa Aesar), 3-aminopropyl-trimethoxysilane (ATMS, 97%, Sigma-Aldrich), α-bromoisobutyryl bromide (BiBB, 98%, Sigma-Aldrich), N,N,N′,N′,N′-pentamethyldiethylenetriamine (PMDETA, 99%, Sigma-Aldrich) were used as received. Double distilled water (18.2 MΩ∙cm, MilliQ system) was used, and other general solvents and chemicals were used as received.

Li M., Qing G., Xiong Y., Lai Y, & Sun T. (2015). CH-π Interaction Driven Macroscopic Property Transition on Smart Polymer Surface. Scientific Reports, 5, 15742.

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