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14 protocols using n octylamine

1

Synthesis and Purification of 4-A2CP

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4-A2CP was synthesized and purified as previously described [14 (link)]. 4-AP, 4-A3CP, 4-amino-2,6-dichlorophenol (4-A2,6DCP), N-octylamine, metyrapone and N,N’-diphenyl-p-phenylenediamine (DPPD), piperonyl butoxide and mercaptosuccinic acid were obtained from the Aldrich Chemical Co., (Milwaukee, WI). All other compounds were obtained from Sigma Co. (St. Louis, MO). For each compound, the highest purity level available was used.
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2

Solution-Processed Optoelectronic Devices

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Lead(ii) iodide powder (PbI2, 99.0%), oleic acid (OAc, 90.0%), and n-octylamine (OAm, 99.0%) were purchased from Aldrich. Hydroiodic acid (HI, 57 wt%), toluene (99.5%), mEthyl acetate (98.0%), and butyl acetate (99.0%) were purchased from Wako Pure Chemical Industries. Propyl acetate (98.0%) was purchased from Tokyo Chemical Industry. Ethyl acetate (99.3%) was purchased from Kanto Chemical Co., Inc. YTZ® balls (ZrO2 beads 50 μm in diameter) were purchased from Nikkato Co., Ltd. Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS, AI4083), poly(4-butylphenyl-diphenyl-amine) (poly-TPD), and tris-[1-phenyl-1H-benzimidazole] (TPBi) were purchased from Clevious and American Dye Source and e-Ray Optoelectronics Technology Co., Ltd. All chemicals were used without purification.
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3

Synthesis of Lead Bromide Perovskite Nanocrystals

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Chemicals: Lead bromide, PbBr2 (99.999%, trace metals basis), n-octylamine (OctAm; 99%), oleic acid (OAc; 90%), triethylamine (TEAm; 99%), N,N-dimethylformamide, (DMF; 99.8%), toluene (anhydrous, 99.7% GC), and benzyl alcohol (BnOH; 99.5%) were all purchased from Sigma-Aldrich. Methylammonium bromide (MABr) was acquired from Dyseol. All chemicals were used without further purification. All experiments were performed under ambient conditions at room temperature.
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4

Quantification of TMAO and Related Metabolites

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Trimethylamine hydrochloride, TMAO, NADPH, magnesium chloride, tris (hydroxymethyl) aminomethane (Trizma® base), Trizma® hydrochloride, n-octylamine, methimazole, L-arginine and formic acid ( ≥ 95%) were purchased from Sigma-Aldrich (St. Louis, MO). Deuterated internal standard (d9-trimethylamine N-oxide) was purchased from Cambridge Isotopes (Cambridge, MA, USA). Optima LC–MS grade water, acetonitrile, and methanol was purchased from Fisher Scientific (Pittsburgh, PA). Taqman® primers used for mRNA quantification were purchased from Applied Biosystems (Foster City, CA). All fluorescent antibodies were purchased from Abcam (Cambridge, MA) (Codes: ab2769, ab8226, ab22717, ab126790, ab195627, ab186693 and ab175774).
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5

Purification and Characterization of Cyclosporine

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Crude
cyclosporine was supplied by Novartis-Massachusetts
Institute of Technology (USA) with purity of 90.8%. Purified cyclosporine
(95.0% purity, crystalline form), n-butylamine, n-octylamine, choline hydroxide, and glacial acetic acid
were purchased from Sigma-Aldrich (Oakville, ON, Canada). Acetonitrile
(HPLC grade), ethyl ether, EtOAc, hexane, phosphoric acid, and tert-butyl methyl ether were purchased from Fisher Scientific
(Ottawa, ON, Canada). The water used in the experiments was obtained
from a Millipore purified water system (resistivity 18.2 MΩ
cm, 25 °C, Milli-Q Academic, Millipore, USA).
[Cho][OAc],
[C4NH3][OAc], and [C8NH3][OAc] were synthesized by following reported procedures (see Supporting Information for complete description
and characterization).32 (link),33 (link) [P66614]Cl was kindly
donated by Cytec-Solvay (Niagara Falls, ON, Canada). [C2mim][OAc] and [C2mim][NTf2] were purchased
from IoLiTec (Tuscaloosa, AL, USA).
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6

Synthesis of Bis(carboxymethyl)trithiocarbonate-based Compounds

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Bis(carboxymethyl)trithiocarbonate,
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxaldehyde
(B-T-CHO), 1,2-dimethoxyethane (DME), 2-butyloctanol, hydrazine monohydrate,
triphenylphosphine (PPh3), diethylene glycol monomethyl
ether, and tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3] were purchased from Tokyo Chemical Industry (Tokyo,
Japan). Phthalimide and azodicarboxylic acid diisopropyl ester (DIAD)
were purchased by Alfa Aesar (Gyeonggi-do, Korea). Piperidine, n-octylamine, potassium phosphate tribasic (K3PO4), tri-tert-butylphosphonium tetrafluoroborate
(P(t-Bu)3·HBF4), and 4,7-dibromobenzo[c]-1,2,5-thiadiazole were purchased from Sigma-Aldrich (Gyeonggi-do,
Korea). Triethylamine (TEA) was purchased from Samchun Chemicals (Seoul,
Korea). All chemicals were used without further purification, and
all reactions were performed under a nitrogen atmosphere with anhydrous
solvents. 3-Octylrhodanine (ORH) was synthesized according to our
previous report.3 (link)
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7

Synthesis of Cadmium Selenide Nanocrystals

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Cadmium chloride (CdCl2, 99.99%), selenium (Se, 99.99%), n‐octylamine (OcAm, 99%), trioctylphosphine (TOP, 97%), chloroform (anhydrous, ≥99%), oleylamine (99%), 1‐octadecene (technical grade, 90%), and octane (anhydrous, ≥99%) were purchased from Sigma Aldrich. Ethyl alcohol (anhydrous, 99.9%) was purchased from Samchun Chemicals. n‐Octylammonium hydrochloride was purchased from Tokyo Chemical Industry. CO gas (99.999%) was purchased from Sumitomo Seika Chemicals.
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8

Synthesis of Semiconductor Nanocrystals

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Di-n-octylamine (+98%), di-n-pentylamine
(99%), di-n-propylamine (99%), diethylamine (>99.5%),
phenethylamine
(≥99%), n-dodecylamine (≥99%), n-octylamine (+99%), n-pentylamine (+99%), n-propylamine (+98%), Cd(OAc)2·2H2O (>98%), trin-octylphosphine (TOP) (97%), and
oleylamine
(or cis-9-octadecenylamine, technical grade, 70%) were obtained from
Sigma-Aldrich. Selenourea (99.9%, metal basis) was obtained from Alpha
Aesar. All were used as received and stored under N2. Toluene
was obtained from Sigma-Aldrich (CHROMASOLV for HPLC, ≥99.9%).
Transmission electron microscopy (TEM) sample grids (Cu with holey
carbon film) were obtained from Ted Pella, Inc.
All synthetic
procedures were conducted under dry N2, except the final
washing steps, which were conducted in the ambient atmosphere. The
reaction mixtures were not stirred. The synthetic products were generally
stored as reaction mixtures, after addition of TOP (see below).
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9

Synthesis of Acrylate and Amine Monomers

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Material Benzylalcohol (≥99%), benzylacrylate (≥99%, contains hydroquinone monomethyl ether (MEHQ) as inhibitor), bisphenol A glycerolate (1 glycerol/phenol) diacrylate (contains 250-500ppm MEHQ as inhibitor), n-butylamine (≥99%), dibutylamine (≥99%), N,Ndiisopropylethylamine (DIPEA, ≥99%) 2-ethylhexylacrylate (98%, contains MEHQ as inhibitor), 2-ethylhexylamine (98%), N-methylbutylamine (≥98%), pentaerythritol triacrylate (PTA, technical grade, contains 600ppm MEHQ as inhibitor), trimethylolpropane triacrylate (TMPTA, technical grade, contains 300-400ppm MEHQ as inhibitor), n-octylamine (99%), were purchased from Sigma-Aldrich. Tetrahydrofuran (THF), and n-hexane were purchased from Acros Organics.
4,4′-methylenebis(cyclohexylamine) (MBCA, >98%) was purchased from TCI. Jeffamine D2000 was kindly provided by Huntsman, and Priamine 1074 was kindly provided by Croda. All reagents were used without further purification unless stated otherwise.
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10

Synthesis of Lead Halide Perovskites

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Lead (II) Iodide (PbI2, 99.999%), Lead (II) Bromide (PbBr2, 99.999%), Oleylamine (>98%), n-Octylamine (99%), Oleic Acid (90%), Acetonitrile (99.8%), N, N-Dimethylformamide, (anhydrous, 99.8%) and Toluene (anhydrous, 99.7%) were purchased from Sigma-Aldrich.
Methylammonium Bromide (MABr) and Methylammonium Iodide (MAI) were purchased from Greatcell Solar. The precursor materials were used without further purification.
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