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7 protocols using benzothiophene

1

Synthesis of Thiophene Derivatives

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Thiophene (99%), 2-ethylThiophene (97%), benzoThiophene (98%), ammonium heptamolybdate (NH4)6Mo7O24, 99%), cobalt (II) nitrate hexahydrate (Co(NO3)2·6H2O, 98%), Nb2O5 (99.99%), HNO3 (70%), dimetyhldisulphide (> 98%), heptane (99%) and diethylamine (> 99.5) were purchased from Sigma Aldrich; γ-Al2O3 (V-250) was purchased from Euro Support, H2 (99.9%), N2 (100%) and He (99.999%) were purchased from Linde Gas. All reagents were used without further purification.
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2

Characterization of Thiophene Derivatives

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Thiophene,
benzoThiophene,
dibenzoThiophene, and 2- and 3-substituted Thiophenes were purchased
from Sigma-Aldrich Corp. and were of the highest quality available.
Outer-dinaphthoThiophene and inner-dinaphthoThiophene were a gift
from Alan Katrizky of the University of Florida. Thiophene-3-carboxylic
acid was recrystallized from ethanol–water as previously described.32 ,33 Appropriate single crystals were selected by microscopic examination
and glued with epoxy cement to an aluminum pin that was then mounted
on a goniometer. The crystal orientation matrix was determined from
laboratory-based X-ray diffraction using an Enraf-Nonius CAD4 diffractometer.
Solutions were prepared in toluene or isopropanol (depending on compound
solubility) at concentrations of 50 mM or less and were placed in
modified SPEX CertiPrep (Metuchen, NJ, USA) X-cell sample cups, employing
a 6 μm thick polypropylene window. Fluorescence self-absorption
artifacts in the X-ray absorption spectra17 (link),18 (link) were checked for by diluting the samples by a factor of 2 and then
remeasuring the spectra. Only data with no measurable self-absorption
are presented in this work.
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3

Synthesis of Sulfur Compounds

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4,7,10-Trioxatridecane-1,13-diamine (purity of 98%), heptane (purity of 99%) and pentane (purity of 99%) were purchased from Merck Company. Also, benzothiophene, dibenzothiophene and dimethyl dibenzothiophene (purities of 98%, from Sigma-Aldrich Co.) were used in this work.
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4

Solvent-Dependent Organic Semiconductors

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Anhydrous toluene, tetralin and DMF were purchased from Sigma-Aldrich Co., Ltd. Two milligrams of the active materials TIPS-PEN, 9,10-bis[(triisopropylsilyl)ethynyl]anthracene, 5,12-bis[(triisopropylsilyl)ethynyl]tetracene, 5,11-bis(triethylsilylethynyl)anthradithiophene and 2,7-dioctyl[1]benzothieno[3,2-b][1]benzothiophene were dissolved in 1 ml of either toluene or tetralin. All solutions were prepared inside a nitrogen-filled glovebox.
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5

Quantifying Sulfur Compounds in Gasoline

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Dibutylsulfide (DBS, purity 100%), ethyl phenyl sulfide (EPS, 97%), benzothiophene (BT, 97%), methylbenzothiophene (MBT, 96%), dibenzothiophene (DBT, 98%), bromocyclohexane (CXB, 99%) and hexane were purchased from Sigma-Aldrich. Dimethyl sulfide (DMS) in Argon gas standard (2.9±0.3 ppm S, v/v) was obtained from Linde AG (Munich, Germany). CO2:Ar (10:90) and O2:Ar (20:80) were supplied by Air Liquide (Madrid, Spain). Commercial gasoline was obtained from a regular gas station (Asturias, Spain). Certified reference material ERM-EF213, consisting of a real "sulfur-free" gasoline (9.1±0.8 ppm S, w/w) was obtained from BAM (Berlin, Germany).
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6

Synthesis and Characterization of Cerium-Vanadium Catalysts

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All materials utilized in this study including cerium(III) nitrate hexahydrate (Ce(NO3)3⋅6H2O), ammonium monovanadate (NH4VO3), bismuth(III) nitrate (Bi5H9N4O22), graphite, hydrazine hydrate (N2H4⋅H2O) (80%), potassium permanganate (KMnO4), hydrogen peroxide (H2O2), hydrochloric acid (HCl), sulfuric acid (H2SO4), normal hexane (C6H14), and benzothiophene (BT) were purchased from Merck and Sigma-Aldrich companies, and used as-received with no further purification. Ultrasound was performed using an ultrasonic 12 mm diameter probe, operating at 20 kHz with an output power of 400 W cm−2 optimized with a calorimeter. XRD (X-ray Diffraction) patterns were analyzed by a Philips-X'PertPro device using Ni-filtered Cu Kα radiation. A Zeiss sigma300-HV device was used to record FESEM (field-emission scanning electron microscope) images. Fourier transform infrared (FT-IR) analysis was performed with a Magna-IR device, a Nicolet 550 spectrometer with a resolution of 0.125 cm−1 in KBr tablets in the range of 400 to 4000 cm−1. EDS (energy dispersive spectroscopy) analysis was performed using a Philips XL30 x-ray scattering device. Reflectance spectrometry (DRS) analysis was performed by Shimadzu model UV3600Iplus. N2 adsorption/desorption (BET) analysis was performed by Belsorp mini x device. To measure the amount of sulfur, a sulfur analyzer in oil model Horiba-SLFA-20 was used.
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7

Sulfur Compound Extraction Optimization

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Tetraethylorthosilicate (TEOS, ≥99%), tetraethyltitanate (TBT, 95%), ethanol (EtOH, ≥99%), nitric acid (HNO3, 69 wt%), benzothiophene (BT, ≥99%), dibenzothiophene (DBT, ≥98%), and isooctane (≥99%) were all obtained from Merck. All chemicals were used without further purification.
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