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12 protocols using dodecylamine

1

Graphite Powder Functionalization Protocol

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Graphite powder (<20 µm) was obtained from Sigma Aldrich (St. Louis, MO, USA). Sulfuric acid (H2SO4, 98%) and hydrogen peroxide (H2O2, 30%) were obtained from R&M Chemicals (Selangor, Malaysia) and used as received. Potassium permanganate (KMnO4, 99.9%) and hydrochloric acid (HCl, 36%) were purchased from SYSTERM (Selangor, Malaysia). Dodecylamine, tetradecylamine, hexadecylamine and octadecylamine were purchased from Acros Organic (Geel, Belgium). All other chemicals were of analytical grade and were used as received without further purification. Distilled water was used for the washings.
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2

Synthesis of Rare-Earth-Doped Luminescent Nanoparticles

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The chemicals used in the various synthesis procedures are LaCl3.6H2O (Strem chemicals, 99.9 %), EuCl3.6H2O (Fisher Scientific, 99.9 %), CeCl3 (Aldrich, 99.99 %), TbCl3.6H2O (Aldrich, 99.9 %), tributyl phosphate (Fluka Analytical, ≥99 %), diphenyl ether (Sigma-Aldrich, 99 %), tributylamine (Sigma-Aldrich, ≥99 %), tridodecylamine (Aldrich, 85 %), phosphoric acid (Aldrich, ≥99.9 %), dihexyl ether (Aldrich, 97 %), dodecylamine (Acros Organics, 98 %), decylamine (Aldrich, 95 %), poly(5)oxyethylene-4-nonylphenyl-ether (Igepal Co 520, Sigma-Aldrich), tetraethyl orthosilicate (TEOS, Sigma-Aldrich, 99 %), and ammonia 28 % in water stored at 7 °C (Sigma-Aldrich, 99.9 %) were used as received. The solvents used are methanol (Sigma-Aldrich, 99.8 %), cyclohexane (Sigma-Aldrich, anhydrous, 99.5 %), ethanol (Alfa Aeasar, 96 %), and toluene (Sigma-Aldrich, anhydrous, 99.8 %) and were used as received.
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3

Synthesis of RNA Oligonucleotides and Gold Nanoparticles

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RNA phosphoramidites for the oligoribonucleotide synthesis were obtained from Sigma-Aldrich (Hamburg, Germany), Cy-5.5 phosphoramidite were purchased from Primetech (Minsk, Belarus). Oleylamine, dodecylamine and stearic acid were supplied from Acros Organics (Geel, Belgium). Dithiothreitol (DTT), cyanuric chloride, diethanolamine, and sodium citrate dihydrate (Na3C6H5O7) were obtained from Sigma-Aldrich (Hamburg, Germany). N,N-diisopropylethylamine (DIPEA) and N-hydroxysuccinimide (NHS) were purchased from Fluka (Seelze, Deutschland). Tetrachloroauric acid (HAuCl4·3H2O) was from Aurat (Moscow, Russia). Uranyl acetate (UA) and phosphotungstic acid (PTA) were purchased from SPI (West Chester, PA, USA). Peptide NH2-(RL)4G-C(O)NH2·5CF3COOH was obtained from Diapharm (Lyubertsy, Russia). Other chemicals and solvents were supplied by Merck (Darmstadt, Germany), Fluka (Seelze, Deutschland) and Panreac (Barcelona, Spain). Water was purified by a Simplicity 185 water system (Millipore, Burlington, MA, USA) and had a resistivity of 18.2 MΩ∙cm at 25 °C.
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4

Synthesis and Purification of Metallic Nanostructures

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All chemicals were used as purchased, without
any further purification: tetrachloroauric (III) acid trihydrate (Sigma-Aldrich,
≥99.9% trace metals basis), formaldehyde solution 37–41%
(Fischer Chemical, analytical reagent grade, stabilized with ca. 12%
methanol), dodecylamine (Acros Organics, 98%), dodecanethiol (Sigma-Aldrich,
≥98%), oleylamine (TCI, >50%), 1,2,3,4-tetrahydronaphthalene
(Fisher Chemicals, ≥97%), tetrabutylammonium bromide (Sigma-Aldrich,
ACS reagent, ≥98.0%). All reagents for organic synthesis were
obtained from Sigma-Aldrich. The reaction products were purified by
column chromatography using SiliCycle Silia Flash P60 (40–63
μm, 60 Å) at an atmospheric pressure or by crystallization.
Thin-layer chromatography was performed using a silica gel 60 Å
F254 (Merck) precoated aluminum substrate and visualized using iodine
vapor and/or a UV lamp (254 nm). All solvents were obtained from Sigma-Aldrich.
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5

Perovskite Nanocrystal Synthesis Protocol

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Oleic acid (OLAc, 90% technical grade, Aldrich), n-decylamine (99%, Acros Organics), dodecylamine (98%, Acros Organics), oleylamine (~90%, Acros Organics), methyl ammonium bromide (MABr, 99%, Sigma-Aldrich), formamidinium bromide (FABr, 98%, Sigma-Aldrich), lead (II) bromide (PbBr2, 98%, Acros Organics), toluene (99.8%, Fisher Chemical), N,N-dimethylformamide (DMF, >99.8%, Aldrich), Ethanol (EtOH, absolute for analysis, Merck). All chemicals listed above were used without any further treatment.
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6

Structural Analysis of Alkylated Berberine Derivatives

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The structure of the product was determined using 1H and 13C NMR spectra. 1H and 13C NMR spectra were recorded on Bruker AV-400 spectrometers (Bruker, Billerica, MA, USA) at 400.13 MHz (1H) and 100.61 MHz (13C) in DMSO-d6. Mass spectra were recorded on a Bruker micrOTOFQ using electrospray ionization (ESI). Silica gel (60–200 mesh, Macherey–Nagel, Düren, Germany) was used for column chromatography; chloroform with gradient of ethanol was used as eluent. Berberine chloride hydrate (TCI Co. (Tokyo, Japan)) was used after oven drying at 95 °C for 5 h. Pentylamine, hexylamine, heptylamine, decylamine, and dodecylamine were purchased from Acros Organics (Geel, Belgium).
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7

Synthesis of Luminescent Lanthanide Nanostructures

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The
chemicals used in the various synthesis procedures were La2O3 (Merck), Eu2O3 (Highways International,
4N), diammonium phosphate (Merck, 99%), LaCl3·6H2O (Strem chemicals, 99.9%), EuCl3·6H2O (Fisher Scientific, 99.9%), tributyl phosphate (Fluka Analytical,
≥ 99%), diphenyl ether (Sigma-Aldrich, 99%), tributylamine
(Sigma-Aldrich, ≥99%), phosphoric acid (Aldrich, ≥99.9%),
dihexyl ether (Aldrich, 97%), dodecylamine (Acros Organics, 98%),
poly(5)oxyethylene-4-nonylphenyl-ether (Igepal Co 520, Sigma-Aldrich),
tetraethyl orthosilicate (TEOS, Sigma-Aldrich, 99%), and ammonia 28%
in water stored at 7 °C (Sigma-Aldrich, 99.9%), methanol (Sigma-Aldrich,
99.8%), cyclohexane (Sigma-Aldrich, anhydrous, 99.5%), ethanol (Alfa
Aeasar, 96%), and toluene (Sigma-Aldrich, anhydrous, 99.8%). All chemicals
were used as received.
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8

Preparation of Nutrient Germinant Mixtures

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Nutrient germinant mixtures were freshly prepared as 2x concentrated solution in 100 mM Tris-HCl buffer pH 7.4, from the following chemicals: L-alanine (Sigma), L-lactate sodium salt (Acros), NaHCO3 (Acros), L-serine (Acros), L-cysteine (Acros), L-threonine (Acros), inosine (Sigma) and D-glucose (Acros). Dodecylamine (Acros) was first dissolved at 1 M in ethanol, and then diluted to 2x of the concentration used in germination experiments (6 mM) in 100 mM Tris-HCl buffer. Stock solutions of 120 mM CaCl2 (Chem Lab, Belgium) and 120 mM DPA (Acros) were made in 100 mM Tris-HCl (pH 7.4), and the pH of the DPA solution was readjusted to pH 7.5 with Trizma base (Sigma-Aldrich). The two solutions were then mixed in a 1:1 volume ratio and eventually further diluted in 100 mM Tris-HCl (pH 7.4) to achieve final Ca2+-DPA concentrations of 60 mM, 50 mM, 30 mM and 20 mM.
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9

Titanium Dioxide Coating on Steel

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Titanium (IV) dioxide (TiO2) also known as titania, hydrochloric acid (37%), sodium hydroxide pallets, and ethanol were purchased from Sigma Aldrich, Darmstadt, Germany. Dodecyl amine (DOC, 98% pure) was purchased from Alfa-Aesar, Ward Hill, MA, United States. Epoxy resin (815C) and EPIKURE as its curing agent were purchased from Sigma Aldrich, Darmstadt, Germany. Plates of plain carbon steel (30L × 30W × 1.0T) mm3 used as substrates were locally purchased. The substrates were polished with silicon carbide (SiC) emery papers from 120 to 800 grit size and then rinsed thoroughly with distilled water.
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10

Synthesis of Multifunctional Nanoparticles

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Ferric chloride hexahydrate (99%), ferrous chloride tetrahydrate (99%), dextran (DX) (M.w. 20,000), zinc chloride (99%), silver nitrate (99.8%), oleylamine (OLA) (70%), benzyl ether (98%), octylphenyl-polyethylene glycol (IGEPAL CA-630), poly(isobutylene-alt-maleic andydride) (PBMA) were purchased from Sigma-Aldrich. Glutathione (GSH) (98%), tetramethylammonium hydroxide (TMAH) (25% solution in methanol), iron(III) acetylacetonate (99%), myristic acid (MA) (99.5%) were purchased from Acros Organics; sodium diethyldithiocarbamate (98%), indium acetate (99.99%), polyethyleneimine (PEI) (99%, M.w. 10,000), zinc acetate (99.98%), copper(I) iodide (99.998%), tetraethylorthosilicate (TEOS) (99%), 3-mercaptopropyltrimethoxysilane (MPTMS) (97%), 1-dodecanethiol (DDT) (98%), dodecylamine (DDA) (98%) were purchased from Alfa Aesar, 3-glycidyloxypropyl-trimethoxysilane (GOPTS) (95%) was from TCI America. All chemical and organic solvents were obtained commercially as analytical-graded materials without further purification.
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