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77 protocols using copper 1 bromide

1

Synthesis of Poly(L-Lactide) via Ring-Opening Polymerization

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l,l-Lactide (LA) was purchased from
Purac (99% Netherlands), crystallized from 2-propanol and stored under
reduced pressure. Paraformaldehyde (99%), p-toluenesulfonic
acid (pTSA, 98%), 3-allyloxypropane-1,2-diol (98%), 3-chloropropane-1,2-diol
(98%), triflic acid (99%), phosphorus pentoxide (P2O5), propanethiol (99%), mercaptoethanol (95%), thioglycolic
acid (98%), propargyl glycidyl ether (98%), propargyl alcohol (97%),
copper (I) bromide, pentamethyldiethylenetriamine (95%, PMDTA), and
sodium azide were purchased from Merck and used without further purification.
Butan-1,4-diol (99%, Acros) was used as received. AIBN was purchased
from Sigma-Aldrich and crystallized from ethanol at 40 °C. Methylene
chloride from POCH was distilled over P2O5 and
maintained under a vacuum. Toluene (95%), hexane (95%), diethyl ether
(98%), and HCl (35%) were purchased from POCH (Gliwice, Poland) and
used as received. Anhydrous ethylene glycol (ethane-1,2-diol) (<99.9%,
Sigma-Aldrich) was used as received.
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2

Synthesis and Characterization of Copper Nanomaterials

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All reagents were in analytical purity and used without further purification. Ethanol (C2H5OH, 99.9%) was purchased from J.T. Baker. Aminophenyl fluorescein solution (APF, C26H17NO5, 98%) was acquired from Life Technologies. A hydrogen peroxide assay kit was acquired from abcam. CopperGreen dyes were acquired from Merck. Copper(I) bromide (CuBr, 98%), Octadecylamine (CH3(CH2)17NH2, 99%), trioctylphosphine oxide ([CH3(CH2)7]3PO, 90%), Oleylamine (CH3(CH2)7CH=CH(CH2)7CH2NH2, 90%), cetyltrimethylammonium bromide (C19H42BrN), Polyvinylpyrrolidone (PVP, (C6H9NO)n, MW = 55,000), hydrogen peroxide solution (H2O2, 30%), Sodium bromide (NaBr, 99.5%), ascorbic acid (C6H8O6, 99%), cetyltrimethylammonium chloride (C19H42ClN, 25%), Sodium borohydride (NaBH4, 99%) and 3-(4,5-dimethylthiazol-2-yl)−2,5-diphenyltetrazolium bromide (MTT, C18H16BrN5S, 97.5%) were bought from Sigma-Aldrich. Water was obtained by using a Millipore direct-Q deionized water system throughout all studies.
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3

Synthesis of Thermoresponsive Polymer Brushes

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1-Vinylimidazole (Aldrich, St. Louis, MO, USA, 99%), 11-bromo-1-undecanol (Aldrich, 98%), 2-bromo-2-methylpropionyl bromide (Aldrich, 98%), water-soluble nonionic azo initiator VA86 (Wako Chemicals, Tokyo, Japan), N,N,N′,N′,N″-pentamethyldiethylenetriamine (PMDETA; Aldrich, 99%), potassium bromide (Aldrich, 99.95%), copper(I) bromide (Aldrich, 99.99%), K2PtCl4 (Aldrich, 98%), NaBH4 (Aldrich, 99%) were used as received without further purifications. N-Isopropylacrylamide (NIPAM; Aldrich, 97%) was recrystallized three times from a mixture of toluene/n-hexane (v/v) 1:1 prior to use. All solvents used were of analytic grade.
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4

Synthesis of Acrylate Polymers via ATRP

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Tert-butyl acrylate (t-BA) (Alfa Aesar, 99%) and n-butyl acrylate (n-BA) (Alfa Aesar, Ward Hill, MA, USA, 98%) were passed through the neutral Al2O3 (Fluka, Buchs, Switzerland) column to remove the inhibitor. Copper(I) bromide (Aldrich, San Diego, CA, USA, 98%), ethyl 2-bromopropionate (EBP) (Aldrich, 98%), N, N, N′, N″, N″-pentamethyldiethylenetriamine (PMDETA) (Acros, Geel, Belgium, 98%), butanone (Fisher Chemical, Hampton, NH, USA, 99%), isopropyl alcohol (Macron, Dunkirk, France), and 3,4,5-trimethoxybenzaldehyde, 98% (Alfa-Aesar) and 1,4-dioxane (Merck, Boston, MA, USA, 99%), HCl (Valerus, Sofia, Bulgaria, 36%), dimethylformamide (DMF) (Merck, 99.9%), methanol (Acros), tetrahydrofuran (THF) (Macron) were used as received.
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5

Synthesis and Purification of Polymeric Precursors

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Tetrahydrofuran (THF), dichloromethane (CH2Cl2), methanol (CH3OH), and N,N-dimethylformamide (DMF) were dried using the solvent purification system PureSolv—EN™ (Innovative Technology, Stratham, NH, USA). Toluene (anhydrous), ethanol, acetone, and n-hexane were obtained from commercial suppliers and used without any further purification procedures unless otherwise stated. Copper (I) bromide (Aldrich, Saint Louis, MO, USA, 99%) was purified by stirring in glacial acetic acid; thereafter, it was thoroughly washed with methanol and anhydrous diethyl ether and dried under vacuum overnight [22 ]. N,N,N,N″,N″-Pentamethyl diethylenetriamine (PMDETA, 99%) and hexamethyldisilazane (HMDS) were obtained from Aldrich (Saint Louis, MO, USA) and used as received.
The synthesis of the polymeric precursors—azide terminated polystyrene, PS-N3; and acetylene terminated polylactic acid, PLA-Ac—is described in the Supplementary Materials. Purification of the synthesized copolymers was performed in a chromatographic column using aluminum oxide (neutral, 0.063–0.200 mm, Merck, Saint Louis, MO, USA) as stationary phase.
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6

Synthesis of Graphene Oxide-Carbon Nanotube Composites

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Graphene oxide (GO) was provided by Promico CO., Ltd (Korea). Carbon nanotubes (CNTs) were provided by LG Chem. (Korea). Sulfur, 2-(dimethylamino)ethyl methacrylate (DMAEMA), iodoethane, hydroquinone, copper(i) bromide, N,N,N′,N′′,N′′-pentamethyldiethylenetriamine, poly(acrylic acid) (Mv = 450 000), poly(vinyl alcohol) (Mw = 9000–10 000, 80% hydrolyzed) were purchased from Aldrich and used as received. 2,2′-Azobis(isobutyronitrile) (AIBN) was purchased from Aldrich and recrystallized in ethanol before use. Carbon black, Super P® conductive, and 2-bromo-2-methylpropionyl bromide were purchased from Alfa Aesar and used as received. All the other reagents and solvents were obtained from reliable commercial sources and used as received.
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7

Pt(IV)-Containing Difunctional Alkyne Synthesis

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DOX and cisplatin were purchased from Beijing Huafeng United Technology Co., Ltd. OEGMA (Mn =480 g/mol, 99%) purchased from Sigma-Aldrich and Co was passed through a neutral alumina column to remove the inhibitor prior to use. Toluene (99%; Aldrich) was refluxed with sodium beads/benzophenone complex and distilled until the solution turned purple. Copper(I) bromide (99.999%; Aldrich), PMDETA (98%; Aldrich), hydrogen peroxide (30%; J&K CHEMICA), sodium vitamin (VcNa; 99%; Aladdin) and succinic anhydride (99%; Aladdin) were used as received without further purification. AzPMA and the difunctional initiator, HBMP, were synthesized according to literature procedures.44 ,45 A Pt(IV)-containing difunctional alkyne was prepared from cisplatin. The experimental procedure is presented in Supplementary materials.
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8

Synthesis of Ga-based Nanoparticles

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Tris(dimethylamido)gallium (III) dimer (Ga2(NMe2)6, 99.9 %) was purchased from ABCR. Copper (I) bromide (99 %), trioctylphosphine oxide (C24H51PO or TOPO, 99 %), oleylamine (C18H35NH2 or OLAM, 70 %), 1-octadecene (C18H36 or ODE, 90 %), toluene (anhydrous, 99.8 %) and ethanol (anhydrous, 99.5 %) were purchased from Sigma-Aldrich.
Hexane (anhydrous, >96 %) was bought from TCI Chemicals. Potassium carbonate (K2CO3, 99+ %, ACS reagent) was obtained from Acros organics. ODE was degassed under vacuum at 110 °C for 4 h, cooled to room temperature, and then transferred in an airtight manner to the glove box. All syntheses were carried out under an inert atmosphere using anhydrous solvents and standard glovebox and Schlenk-line techniques. NPs washing, handling, and storage were also carried out under inert atmosphere.
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9

Multifunctional Nanocarrier Synthesis

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Bis(2-hydroxyethyl) disulfide, 1,1,4,7,10,10-hexamethyltriethylenetetramine (HMTETA), copper (I) bromide (CuBr), iron (III) acetylacetonate (Fe(acac)3), oleic acid, tri-octylamine, DOX, (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (EDC), N-hydroxysuccinimide (NHS) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) were purchased from Sigma. Amberlite® IR120, 2-bromo-2-methylpropionyl bromide, CL, rhodamine 123 (R123), GSH and pyrene were purchased from Acros. Neutral aluminium oxide (Al2O3) was purchased from Seedchem Company. Tin (Ⅱ) 2-ethylhexanoate (Sn(Oct)2) and o-phenylenediamine were purchased from Alfa Aesar. Dithiothreitol (DTT) was purchased from J.T. Baker. Tert-butyl methacrylate (tBMA) and trimethylamine (TEA) were purchased from TCI. Polyvinyl alcohol (PVA, MW=2000) was purchased from Showa. Minimum essential medium, penicillin, streptomycin and fetal bovine serum (FBS) were purchased from Biological Industries. The annexin-V/PI staining kit was purchased from Strong Biotech Corporation. Dulbecco’s modified Eagle’s medium (DMEM) was purchased from Invitrogen.
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10

Spray-Dried Sulfated Cellulose Nanocrystals

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Spray-dried sulfated CNCs (prepared by sulfuric acid mediated hydrolysis of hardwood pulp) was kindly supplied by InnoTech Alberta Inc (Edmonton, AB, Canada). The spray-dried CNC powder was stored at 4 °C and used as obtained. Triethylamine (TEA), 4-dimethyl-aminopyridine (DMAP), 2-bromoisobutyryl bromide, N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA), copper (I) bromide, [2-(methacryloyloxy)ethyl] trimethylammonium chloride (METAC) (75 wt% in H2O), 2-aminoethyl methacrylate hydrochloride (AEM), 2,2′-bipyridyl (bpy), methanol, ethanol, tetrahydrofuran (THF), acetone, and potassium bromide (KBr) were purchased from Sigma-Aldrich (St Louis, MO, USA).
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