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15 protocols using 4 dodecylbenzenesulfonic acid

1

Fabrication of Organic Transistor Channels

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PEDOT:PSS (Clevios PH1000) was purchased from Heraeus. Chitosan (low molecular weight), d-sorbitol (≥99.5%; BioUltra), (3-glycidyloxypropyl)trimethoxysilane, 4-dodecyl benzene sulfonic acid, 3-(trimethoxysilyl)propyl methacrylate (A-174 silane), branched PEI and acetic acid were purchased from Sigma-Aldrich. Micro-90 concentrated cleaning solution was purchased from Special Coating Services. AZ nLOF 2020 (negative photoresist), AZ 10XT (positive photoresist), AZ 400K and AZ 300 MIF (metal ion free) developers were acquired from MicroChemicals, Merck. To create the transistor channel, a mixture of PEDOT:PSS aqueous dispersion and d-sorbitol (40 wt%) was prepared and mixed with (3-glycidyloxypropyl)trimethoxysilane (1.0 wt%) and 4-dodecyl benzene sulfonic acid (0.1 wt%). PEI was diluted in deionized water (1:10). Chitosan (0.5 wt%) was diluted in deionized water and mixed with acetic acid (6.0 wt%).
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2

Synthesis of BBL Polymer for Electronics

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Poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PSS, Clevios PH1000) was purchased from Heraeus Holding. Naphthalenetetracarboxylic dianhydride (NDA), 1,2,4,5-tetraaminobenzene tetrahydrochloride (TABH), poly(phosphoric acid) (PPA), methanesulfonic acid (MSA), chloroform, 1,2-dichlorobenzene, ethylene glycol, (3-glycidyloxypropyl)trimethoxysilane and 4-dodecylbenzenesulfonic acid were purchased from Sigma-Aldrich. BBL (η = 6.3 dl g−1 in MSA at 30 °C, Mw = 35 kDa) was made by polycondensation of NDA and TABH in PPA at elevated temperatures17 (link),31 (link).
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3

Fabrication of PEDOT:PSS-based Devices

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PEDOT:PSS (Clevios PH1000) was purchased from Heraeus. d-Sorbitol (≥99.5%; BioUltra), (3-glycidyloxypropyl)trimethoxysilane (GOPS), 4-dodecyl benzene sulfonic acid (DBSA), PBS tablets, and 3-(trimethoxysilyl)propyl methacrylate (A-174 silane) were purchased from Sigma-Aldrich. Micro 90 concentrated cleaning solution was purchased from Special Coating Services. AZnLOF2020 (negative photoresist), AZ9260 (positive photoresist), AZ 400 K, and AZ 300 metal ion–free developers were acquired from MicroChemicals, Merck. Neodymium magnets were purchased from K&J Magnetics (DH101, D301). PCB circuits were manufactured by Eurocircuits. Electronic components were ordered from Digi-key. Type 321 0.002″ stainless steel sheet was purchased from SSTW. Gold plating solution was purchased from Gold Plating Services.
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4

Synthesis of Biobased Polymeric Materials

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ε-caprolactone (ε-CL, purity: 97%, MW = 114.14 g/mol), p-coumaric acid (PCA, purity: ≥98.0%, MW = 164.16 g/mol), and 4-dodecylbenzenesulfonic acid (DBSA, purity: ≥95%, MW = 326.49 g/mol) were purchased from Sigma-Aldrich and used without further purification.
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5

Fabrication of Organic Transistor Channels

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PEDOT:PSS (Clevios PH1000) was purchased from Heraeus. Chitosan (low molecular weight), d-sorbitol (≥99.5%; BioUltra), (3-glycidyloxypropyl)trimethoxysilane, 4-dodecyl benzene sulfonic acid, 3-(trimethoxysilyl)propyl methacrylate (A-174 silane), branched PEI and acetic acid were purchased from Sigma-Aldrich. Micro-90 concentrated cleaning solution was purchased from Special Coating Services. AZ nLOF 2020 (negative photoresist), AZ 10XT (positive photoresist), AZ 400K and AZ 300 MIF (metal ion free) developers were acquired from MicroChemicals, Merck. To create the transistor channel, a mixture of PEDOT:PSS aqueous dispersion and d-sorbitol (40 wt%) was prepared and mixed with (3-glycidyloxypropyl)trimethoxysilane (1.0 wt%) and 4-dodecyl benzene sulfonic acid (0.1 wt%). PEI was diluted in deionized water (1:10). Chitosan (0.5 wt%) was diluted in deionized water and mixed with acetic acid (6.0 wt%).
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6

Functionalized Silica Nanoparticles for Bacterial Inhibition

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Fossil Shell Flour Diatomaceous Earth was purchased from Perma-Guard, Inc. (Bountiful, UT). 200 proof ethanol was obtained from Decon Laboratories, Inc. (King of Prussia, PA). Toluene and methanol were purchased from Fischer Scientific (Waltham, MA). (3-Aminopropyl)triethoxysilane (APTES), l-cysteine hydrochloride monohydrate, 4-dodecylbenzenesulfonic acid, Ellman’s Reagent (5,5′-dithiobis(2-nitrobenzoic acid), DTNB), glycine hydrochloride, 1,4,8,11-tetraazacyclotetradecane (cyclam), tert-butyl nitrite, and potassium cyanide (KCN) were purchased from Sigma-Aldrich (St. Louis, MO). N-(6-Aminohexyl)aminomethyltriethoxysilane (AHAMTES) and 3-aminopropyldimethylethoxysilane (APDMES) were purchased from Gelest, Inc. (Morrisville, PA). Sodium acetate was obtained from EMD Chemicals, Inc. (Gibbstown, NJ). The bacterial strain Staphylococcus aureus (ATCC 6538) and mouse 3T3 cells (ATCC 1658) were originally purchased from American Type Culture Collection (ATCC).
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7

Synthesis of Conducting Polymers

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l-aspartic acid, phosphoric acid (85%), and hydrochloric acid (HCl, 35%) were obtained from Panreac. 1,4-Diaminobutane (DAB, 99%), imidazole, 4-dodecylbenzenesulfonic acid (DBSA), 3,4-ethilendioxitiophene (EDOT, 97%), hydroxmethyl-3,4-ethylenedioxythiophene (HMeDOT, 95%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Dimethyl sulfoxide (DMSO, dried, max. 0.025% H2O), methanol (MeOH, 99.9%), potassium chloride, mesitylene, and sulfolane were acquired from Merck (Darmstadt, Germany).
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8

Synthesis of Pyrrole-Functionalized PAN Nanocomposites

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PAN (MW 50 000–70 000 Da, 99%) was purchased from Sarchem Laboratories Inc., New Jersey. Pyrrole (98%), ammonium peroxydisulfate (APS), 4-dodecylbenzene sulfonic acid (DBSA) 99%, HCl 12 M, Rhodamine B (RB), Methyl Orange (MO), and naphthalene were purchased from Sigma Aldrich, 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) from Enzo Life Sciences Inc., New York. Dimethylformamide (DMF) was supplied by Fisher Scientific, H3PO4 (85%) by Carlo Erba, CH3CN (Chromasolv for HPLC, purity ≥ 99.9%) by Honeywell. All the chemicals were used without further purification. Water was purified with a Milli-Q plus apparatus (TOC = 2 ppb, conductivity 18.2 MΩ cm). The commercial multiwalled carbon nanotubes employed were Nanocyl™ NC7000 industrial grade, purchased from Nanocyl S.A., Belgium. Their reported features were: 18 outer mean diameter 9.5 nm, average length 1.5 μm, specific surface area 475 m2 g−1, amorphous carbon pyrolytically deposited on the outer layer, C purity 90%, and metal oxides content 10% (1% transition metals). Reported impurities, determined by inductively coupled plasma mass spectrometry (ICP-MS), were: Al (5.9 wt%), Fe (0.5 wt%), and Co (0.2 wt%). This material was used without any further purification and is referred to in this article as CNT(NP), where NP stands for NanoParticles or Non-Purified.
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9

Synthesis and Characterization of N-Substituted Cyclic Carbonates

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Lactic acid solution (≥85%), 1-butyl-3-methylimidazolium chloride (≥99%), ethylene glycol (≥99%), polyethylene glycol 8000 (USP), 4-dodecylbenzenesulfonic acid (≥95%), acetic acid (≥99%), 3-methacryloxypropyltrimethoxysilane (>98%), and 1,8-diazabicyclo[5.4.0]undec-7-ene (≥99%) were purchased from Sigma Aldrich (St. Louis, MO, USA). CleviosTM PH-1000 (PEDOT:PSS) was purchased from Heraeus (Hanau, Germany). AmberlystTM A-26 (OH-form) and analytical grade solvents were purchased from Fisher Scientific (Hampton, NH, USA). Deuterated solvents were purchased from Deutero (Kastellaun, Germany). The N-substituted eight membered cyclic carbonates: 6-methyl-1,3,6-dioxazocan-2-one (8MC) and 6,6′-(ethane-1,2-diyl)bis(1,3,6-dioxazocan-2-one) bis-8MC were synthesized using the previously reported procedures [19 (link),20 (link)]. ILs were prepared using AmberlystTM A-26 (OH-form) exchange resin following the procedure in the literature [21 (link)], ILs were stored inside a N2 filled glovebox (H2O and O2 < 5 ppm). 1H- and 13C-NMR spectra were recorded with a Bruker Avance DPX 300 spectrometer. The NMR chemical shifts were reported as δ in parts per million (ppm) relative to the traces of non-deuterated solvent. Fourier transform infrared-attenuated total reflection (FTIR-ATR) spectroscopy was performed with a Bruker Alpha.
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10

Fabrication of Conductive Agarose Hydrogels

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Agarose (Thermo Fisher Scientific, Waltham, MA) was dissolved in ultrapure water to 2.5 wt% and mixed with PEDOT:PSS (PH1000, Ossila, Sheffield, UK) and water in various ratios to make hydrogels with final concentrations of 0.5 or 1.0 wt% Agarose and 0.0, 0.2 or 0.6 wt% PEDOT:PSS (Table 1). PEDOT:PSS was sonicated for 15 min prior to hydrogel fabrication, and water was warmed to extend gelation time, allowing for adequate mixing. Hydrogel pre-polymer was deposited into glass-mounted PDMS molds (1.5 mm thick x 8 mm I.D.) and allowed to set at room temperature for at least 10 min to make 80 μL gels. After complete gelation, hydrogels were transferred to 24 well plates containing 1 mL of either αMEM (Invitrogen, Waltham, MA) supplemented with 10% FBS (GenClone, San Diego, CA) and 1% penicillin-streptomycin (Gemini Bio Products) or ultrapure water to remove any unreacted reagents. Gels stored in αMEM were maintained in standard cell culture conditions (i.e., 37°C, 5% CO2), whereas gels stored in water were kept at room temperature. Pure PEDOT:PSS gels were fabricated by mixing PEDOT:PSS and 4-dodecylbenzenesulfonic acid (Sigma, St. Louis, MO) at 3 v/v% according to Zhang et al.[27 (link)] and used as controls for some biochemical assays (Fig. S1A).
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