33527-91-2

Usage

Uses

Used in Polymer Synthesis:
TRIS(2-DIMETHYLAMINOETHYL)AMINE is used as an atom transfer radical polymerization (ATRP) ligand for the creation of telechelic polymers. It plays a crucial role in the synthesis of polymers with controlled molecular weights and architectures, which are essential in various industries.
Used in Alkali-Metal-Mediated Synthetic Applications:
TRIS(2-DIMETHYLAMINOETHYL)AMINE is used as a tripodal polyamine ligand for forming complexes with group 1 metals. This application is significant in alkali-metal-mediated synthetic processes, where the ligand's ability to form stable complexes enhances the efficiency and selectivity of the reactions.
Used in Macrocyclization Processes:
TRIS(2-DIMETHYLAMINOETHYL)AMINE is used as a reactant in macrocyclization processes by reacting with tripodal esters in methanol to give tricyclic cryptands. This application is important in the synthesis of complex molecular structures with potential applications in various fields, such as pharmaceuticals and materials science.
Used in Chemical Research:
As a versatile ligand, TRIS(2-DIMETHYLAMINOETHYL)AMINE is also used in chemical research to explore new reactions and develop novel synthetic methods. Its ability to form complexes with various metals and participate in different types of reactions makes it a valuable tool for researchers in the field of chemistry.

InChI:InChI=1/C12H30N4/c1-13(2)7-10-16(11-8-14(3)4)12-9-15(5)6/h7-12H2,1-6H3

Upstream product

• 50-00-0 formaldehyd 
• 14350-52-8 tris-(2-aminoethyl)amine tetrahydrochloride 
• 555-77-1 tris-(2-chloro-ethyl)-amine 
• 124-40-3 dimethyl amine 
• 64-18-6 formic acid 
• 4097-89-6 2,2',2''-triaminotriethylamine 

Downstream Products

• 40538-81-6 bis(2-N',N'-dimethylaminoethyl)amine 
• 625832-69-1 [(tris(2-dimethylaminoethyl)amine)Zn](ClO₄)(BPh₄) 
• 1240262-08-1 [Fe(tris(N,N-dimethylaminoethyl)amine)Cl)]BPh₄*CH₃CN 
• 35090-00-7 PhCH₂Na*Me₆TREN 
• 1309874-42-7 [Cu(I)(tris[2-(dimethylamino)ethyl]amine)(PPh₃)][BPh₄] 
• 1402045-99-1 N,N-bis(2-dimethylaminoethyl)benzamide 

Relevant academic research and scientific papers

Luminescent Nanocellulose Platform: From Controlled Graft Block Copolymerization to Biomarker Sensing

A strategy is devised for the conversion of cellulose nanofibrils (CNF) into fluorescently labeled probes involving the synthesis of CNF-based macroinitiators that initiate radical polymerization of methyl acrylate and acrylic acid N-hydroxysuccinimide ester producing a graft block copolymer modified CNF. Finally, a luminescent probe (Lucifer yellow derivative) was labeled onto the modified CNF through an amidation reaction. The surface modification steps were verified with solid-state 13C nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy. Fluorescence correlation spectroscopy (FCS) confirmed the successful labeling of the CNF; the CNF have a hydrodynamic radius of about 700 nm with an average number of dye molecules per fibril of at least 6600. The modified CNF was also imaged with confocal laser scanning microscopy. Luminescent CNF proved to be viable biomarkers and allow for fluorescence-based optical detection of CNF uptake and distribution in organisms such as crustaceans. The luminescent CNF were exposed to live juvenile daphnids and microscopy analysis revealed the presence of the luminescent CNF all over D. magna's alimentary canal tissues without any toxicity effect leading to the death of the specimen. (Graph Presented).

Hemicellulose-based multifunctional macroinitiator for single-electron- transfer mediated living radical polymerization

A multifunctional macroinitiator for single-electron-transfer mediated living radical polymerization (SET-LRP) was designed from acetylated galactoglucomannan (AcGGM) by α-bromoisobutyric acid functionalization of the anomeric hydroxyl groups on the heteropolysaccharide backbone. This macroinitiator, with a degree of substitution of 0.15, was used in the SET-LRP of methyl acrylate, catalyzed by Cu0/Me6-TREN in DMSO, DMF, or DMSO/H2O in various concentrations. Kinetic analyses confirm high conversions of up to 99.98% and a living behavior of the SET-LRP process providing high molecular weight hemicelluloses/methyl acrylate hybrid copolymers with a brush-like architecture.

Copper catalyzed ring opening copolymerization of a vinyl cyclopropane and methyl methacrylate

Vinyl cyclopropanes are an important class of monomers which on radical ring opening polymerization (RROP) lead to polymers having cyclic moieties, carbon-carbon unsaturation and different other functional groups inside its backbone as in the pendant group. This investigation reports controlled radical ring opening polymerization (CRROP) of 1,1-bis (ethoxy carbonyl)-2- vinylcyclopropane (BCVCP) catalyzed by Cu catalyst. In this case homo and co-polymerization of BCVCP was carried out via ATRP using ethyl-2- bromoisobutyrate as initiator and CuBr as catalyst in combination with Me 6-TREN ligand. Radical polymerization of BCVCP and its copolymerization with methyl methacrylate (MMA) via ATRP led to predominantly 1,5 ring opening polymerization leading to linear polymers with >CC in the main chain of the polymer. Conventional free radical co-polymerization of BCVCP and MMA led to polymers predominantly with cyclic rings in the main chain. The polymers were characterized by NMR, FT-IR, GPC, DSC and TGA analysis. The Royal Society of Chemistry 2013.

Synthesis of SET-LRP-induced galactoglucomannan-diblock copolymers

Polysaccharides are biorenewable and biodegradable starting materials for the development of functional materials. The synthesis of a monofunctional macroinitiator for single electron transfer-living radical polymerization was successfully developed from a wood polysaccharide-O-acetyl galactoglucomannan (GGM) using a beforehand synthesized amino-functional α-bromoisobutyryl derivative applying reductive amination. The GGM macroinitiator was employed to initiate a controlled radical polymerization of [2-(methacryloyloxy)ethyl] trimethylammonium chloride (MeDMA), methyl methacrylate (MMA), and N-isopropylacrylamide (NIPAM) using Cu0/Me6-Tren as a catalyst. The either charged or amphiphilic GGM-b-copolymers with different chain lengths of the synthetic block were successfully synthesized without prior hydrophobization of the GGM chain and dimethyl sulfoxide (DMSO) or DMSO/water mixtures were used as solvents. This novel synthetic approach may find untapped potentials particularly for the development of polysaccharide-based amphiphilic additives for cosmetics or paints and for the design of novel temperature or pH responsive polymers with such potential applications as in drug delivery systems or in biocomposites. Copyright

Macroinitiator halide effects in galactoglucomannan-mediated single electron transfer-living radical polymerization

Chloro (Cl)- and bromo (Br)-functionalized macroinitiators were successfully prepared from the softwood hemicellulose O-acetylated galactoglucomannan (AcGGM) and then explored and evaluated with respect to their ability and efficiency of initiating single electron transfer-living radical polymerization (SET-LRP). Both halogenated species effectively initiate SET-LRP of an acrylate and a methacrylate monomer, respectively, yielding brushlike AcGGM graft copolymers, where the molecular weights are accurately controlled via the monomer:macroinitiator ratio and polymerization time over a broad range: from oligomeric to ultrahigh. The nature of the halogen does not influence the kinetics of polymerization strongly, however, for acrylate graft polymerization, AcGGM-Cl gives a somewhat higher rate constant of propagation, while methacrylate grafting proceeds slightly faster when the initiating species is AcGGM-Br. For both monomers, the macroinitiator efficiency is superior in the case of AcGGM-Br.

Star-shaped trimeric quaternary ammonium bromide surfactants: Adsorption and aggregation properties

Novel star-shaped trimeric surfactants consisting of three quaternary ammonium surfactants linked to a tris(2-aminoethyl)amine core were synthesized. Each ammonium had two methyls and a straight alkyl chain of 8, 10, 12, or 14 carbons. The adsorption and aggregation properties of these tris(N-alkyl-N,N- dimethyl-2-ammoniumethyl)amine bromides (3CntrisQ, in which n represents alkyl chain carbon number) were characterized by equilibrium and dynamic surface tension, rheology, small-angle neutron scattering (SANS), and cryogenic transmission electron microscopy (cryo-TEM) techniques. 3C ntrisQ showed critical micelle concentrations (CMC) 1 order of magnitude lower than that of the corresponding gemini surfactants with an ethylene spacer and the corresponding monomeric surfactants. The logarithm of the CMC decreased linearly with increasing hydrocarbon chain length for 3C ntrisQ. The slope of the line, which is well-known as Klevens equation, was larger than those of the monomeric and gemini surfactants; however, considering the total carbon number in the chains, the slope was shallower than the monomeric and was close to the gemini. Through the results such as surface tensions at the CMC (32-34 mN m-1) and the parameters of standard free energy, CMC/C20 and pC20, it was found that 3CntrisQ could adsorb densely at the air/water interface despite the strong electrostatic repulsion between multiple quaternary ammonium headgroups. Moreover, dynamic surface tension measurements showed that the kinetics of adsorption for 3CntrisQ to the air/water interface was slow because of their bulky structures. Furthermore, the results of rheology, SANS, and cryo-TEM determined that 3CntrisQ with n = 10 and 12 formed ellipsoidal micelles at low concentrations in solution and the structures transformed to threadlike micelles with very few branches for n = 12 as the concentration increased, but for n = 14 threadlike micelles formed at relatively low concentrations.

A cobalt(ii) complex with unique paraSHIFT responses to anions

ParaSHIFT agents have shown promise in detecting chemical targets in biological systems by magnetic resonance, but few studies have used transition metal complexes for this purpose. Here we report our investigations into CoMe6trenCl (tren = tris(2-aminoethyl)amine) as a paraSHIFT agent. The paramagnetic region of the 1H NMR spectrum shows characteristic spectral profiles in the presence of fluoride, acetate, lactate and citrate in aqueous solution. These distinctive NMR shifts of each anion are maintained even in mixtures of anions.

Physicochemical and solution properties of quaternary-ammonium-salt-type amphiphilic trimeric ionic liquids

The quaternary-ammonium-salt-type amphiphilic compounds 3Cntris-s-Q X (star-type; carbon number between the central amino and ammonium groups s = 2, 3) and 3Cnlin-3-Q X (linear-type; carbon number between the hydrophilic groups s = 3), where n represents the alkyl chain length (n = 8, 10, 12, 14) and X represents a counterion [hexafluorophosphate, trifluoromethanesulfonate (OTf), bis(fluorosulfonyl)amide (FSA), and bis(trifluoromethanesulfonyl)amide (NTf2)], were synthesized. Except for 3C12tris-3-Q OTf, these trimeric compounds presented melting points lower than 100 °C and therefore are defined as ionic liquids. Among them, 3Cntris-3-Q NTf2 (n = 8, 12, 14) and 3Cnlin-3-Q NTf2 (n = 8, 10) presented melting points lower than 0 °C. The melting points of the amphiphilic trimeric ionic liquids (n = 8, 10), which were lower for the star- than for the linear-type compounds, were higher than those of the corresponding monomeric compounds but lower than those of the corresponding gemini samples. Moreover, the amphiphilic trimeric ionic liquids exhibited higher conductivities and lower viscosities than the corresponding gemini ionic liquids, while the star-type trimeric ionic liquids presented lower conductivities and higher viscosities than those of the linear-type compounds. The amphiphilic trimeric ionic liquids also readily adsorbed at the air/water interface and oriented themselves to form micelles in aqueous solution. This aggregation behavior was not observed in the monomeric and gemini ionic liquids.

A mononuclear cobalt complex with an organic ligand acting as a precatalyst for efficient visible light-driven water oxidation

N,N′-Bis(salicylidene)ethylenediaminecobalt(ii) (1) has been investigated as a highly efficient water oxidation precatalyst with a TON of 854 at pH = 9.0, using [Ru(bpy)3](ClO4)2 as a photosensitizer and Na2S2O8 as a sacrificial electron acceptor. The Royal Society of Chemistry.

Synthesis of inimers and hyperbranched polymers

An inimer, and process for making same, having the following formula: wherein X=halogen, nitroxide, thioester; R═H or CH3; and R′=aliphatic, non-aliphatic, linear or branched, mesogenic, non mesogenic, chiral, achiral, hydrocarbon, non-hydrocarbon, selected from fluorocarbon, oligo(oxyethylene) and siloxane substituents, alkyl, aryl, mesogenic group, non-mesogenic group, aliphatic, non-aliphatic, siloxane, perfluoroalkyl, perfluoroaryl, or other fluorocarbon group, and polymers, and the process of making them, from the inimer.