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1 hexanethiol

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1-hexanethiol is a chemical compound with the formula CH3(CH2)5SH. It is a colorless liquid with a characteristic unpleasant odor. 1-hexanethiol is commonly used as a reagent in various chemical applications, particularly in organic synthesis and analysis.

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Lab products found in correlation

Chloroform, by Merck Group (3 mentions) 6 mercaptohexanoic acid, by Merck Group (2 mentions) 1 propanethiol, by Merck Group (2 mentions) Triethylamine, by Merck Group (2 mentions) Butyl 3 mercaptopropionate, by Merck Group (2 mentions) 1 dodecanethiol, by Merck Group (2 mentions) Oleic acid, by Merck Group (2 mentions) Nickel 2 chloride, by Merck Group (1 mentions) Ethylenediaminetetraacetic acid edta, by Merck Group (1 mentions) 6 mercapto 1 hexanol, by Merck Group (1 mentions) 11 mercapto 1 undecanol, by Merck Group (1 mentions) Npg 10, by Bruker (1 mentions) Hydrogen peroxide, by Avantor (1 mentions) Trisodium citrate dihydrate, by Merck Group (1 mentions) Sodium borohydride, by Avantor (1 mentions) Hepes, by Avantor (1 mentions) Sodium oleate, by Merck Group (1 mentions) Sodium chloride (nacl), by Avantor (1 mentions) Hydrochloric acid (hcl), by Avantor (1 mentions) Tween 20, by Merck Group (1 mentions)

10 protocols using 1 hexanethiol

1

Characterization of Fibronectin Binding

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Full-length human plasma fibronectin (fc010) and recombinant human fibronectin fragment 3 protein, CF (FN-050; Carrier free histidine-tagged FNIII8–14 fragment) were obtained from Millipore Limited (Hertfordshire, UK) and R&D systems (Minneapolis, Minnesota, USA) respectively, and the trisNTA-EG3-C16-SH linker was synthesized as described previously37 (link)–39 (link). Gold-coated QCM crystals were supplied by openQCM (Novaetech S.r.l., Napoli, Italy) and gold-coated AFM chips (NPG-10) were purchased from Bruker (UK) Limited (Coventry, UK). The chemicals/reagents, ethanol (> 99.5% for HPLC), hydrogen peroxide solution (30% w/w in water), concentrated sulfuric acid (99.999%), 1-hexanethiol (HS–(CH2)5–CH3), 6-mercaptohexanoic acid (HS–(CH2)5–COOH), 6-amino-1-hexanethiol (HS–(CH2)6–NH2), 6-mercapto-1-hexanol (HS–(CH2)6–OH), 11-mercapto-1-undecanol (HS–(CH2)11–OH), nickel (II) chloride and ethylenediaminetetraacetic acid (EDTA) were obtained from Sigma-Aldrich (Dorset, UK), whereas tris(2-carboxyethyl)phosphine (TCEP), 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), phosphate buffered saline (PBS) tablets and sodium chloride were acquired from Fisher Scientific UK Ltd. (Loughborough, UK). All solutions were prepared using deionized water of HPLC grade (Sigma Aldrich, Dorset, UK).
Liamas E., Black R.A., Mulheran P.A., Tampé R., Wieneke R., Thomas O.R, & Zhang Z.J. (2020). Probing fibronectin adsorption on chemically defined surfaces by means of single molecule force microscopy. Scientific Reports, 10, 15662.
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2

Synthesis and Characterization of Silver Nanoparticles

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Trisodium citrate dihydrate (Cit) 99% (Na3C6H3O7), 1-hexanethiol (HT) 95% (CH3(CH2)4CH2SH), 1-propanethiol (PT) 99% (CH3CH2CH2SH) and chloroform were purchased from Sigma Aldrich (St. Louis, MO, USA). Silver nitrate 98% (AgNO3) was purchased from G. Frederick Smith Chemical Company (GFS) (Powell, OH, USA). Hydrogen peroxide 30% (H2O2), HEPES, and sodium borohydride 99% (NaBH4) were obtained from VWR Chemicals (Radnor, PA, USA). L-α-phosphatidylcholine was purchased from Avanti Lipids Alabaster, AL, USA). Sodium Oleate (SOA) 97% was obtained from Tokyo Chemical Industry Co, Ltd. (Portland, OR, USA). Ten mM sodium phosphate buffer was prepared for PC suspension at pH 8. Instant Ocean Salts were purchased from Aquatic Ecosystems (Forth Collins, CO, USA). Nanopure water was obtained from a Milli-Q ultrapure system. All chemicals were used as received.
Harper B.J., Engstrom A.M., Harper S.L, & Mackiewicz M.R. (2024). Impacts of Differentially Shaped Silver Nanoparticles with Increasingly Complex Hydrophobic Thiol Surface Coatings in Small-Scale Laboratory Microcosms. Nanomaterials, 14(8), 654.
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3

Synthesis and Characterization of Gold Nanoparticles

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Aqueous solutions of 5, 10, and 20 nm gold citrate-capped NPs were purchased from Ted Pella, characterization information has been provided in Table S1. Chloroform (CHCl3) and L-α-phosphatidylcholine-hydrogenated soy (HPC) were purchased from Sigma-Aldrich while 1.2-dipalmitoyl-d62-sn-glycero-3-phosphocholine (dDPPC) was from Avanti Polar Lipids Inc, Alabaster, AL, USA. Ninety-five percent 1-hexanethiol (HT) and sodium oleate were purchased from Sigma-Aldrich. Tween-20 was purchased from Sigma-Aldrich. Sodium phosphate monobasic monohydrate, sodium phosphate dibasic heptahydrate, sodium chloride, and hydrochloric acid were from BDH Chemicals. Sodium bicarbonate was from J.T. Baker. Nanopure water was from a Milli-Q ultra-pure system. Potassium cyanide (KCN) was from Mallinckrodt. All reagents were used as received.
Engstrom A.M., Faase R.A., Marquart G.W., Baio J.E., Mackiewicz M.R, & Harper S.L. (2020). Size-Dependent Interactions of Lipid-Coated Gold Nanoparticles: Developing a Better Mechanistic Understanding Through Model Cell Membranes and in vivo Toxicity. International Journal of Nanomedicine, 15, 4091-4104.
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4

Synthesis of Thiol-Ene Photocurable Resins

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2,2,6,6-Tetramethyl piperidine (TMP), divinyl sulfone (DVS), 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO), 1-hexanethiol (HT), butyl 3-mercaptopropionate (BT), butyl acrylate, triethylamine (TEA), (2,2,6,6-Tetramethylpiperidin-1-yl) oxyl (TEMPO), and diethyleneglycol diethyl ether (DEGDE), triethylene glycol diacrylate (TEGDA) were purchased from Sigma-Aldrich. Pentaerythritol tetra(3-mercaptopropionate) (PETMP) was donated by Bruno Bock. All chemicals were used as received. Tetra (2-mercaptoethyl) silane (SiTSH) was synthesized according to a previously reported procedure.37 Molecular structures are depicted in Fig. 1.
Zhang X., Huang S., Podgórski M., Han X., Claudino M, & Bowman C.N. (2018). Assessment of TEMPO as a Thermally Activatable Base Generator and Its Use in Initiation of Thermally-Triggered Thiol–Michael Addition Polymerizations. Polymer chemistry, 9(32), 4294-4302.
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5

Synthesis of Functionalized Thiol Ligands

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1-propanethiol (99%), 3-mercaptopropionic acid (99%), 1-hexanethiol (95%), 1-dodecanethiol (98%), 11-bromoundecanoic acid (95%), triphenylphosphine (99%), N1,N1-dimethyl-1,3-propanediamine (99%), 4-(N,N-dimethylamino) pyridine (99%), triethylamine (Et3N), N,N’-dicyclohexylcarbodiimide (DCC), poly(ethylene glycol) (average MW = 600), poly(ethylene glycol) methyl ether (average MW = 750), sodium borohydride (99.99%, granular), tetrachloroauric acid trihydrate (99.9%) and potassium thioacetate (98%) were purchased from Sigma Aldrich (St. Louis, MO). Silver nitrate (99.9%), 1,3-propanesultone (99%) and 1,1’-carbonyldiimidazole (CDI) (97%) were purchased from Alfa-Aesar (Wardhill, MA). The solvents used in this study (ethanol, dimethyl formamide, chloroform, ethyl acetate, etc.) were also purchased from Sigma-Aldrich and used as purchased. Column purification chromatography of the synthesized ligands was performed using silica gel (60 Å, 230–400 mesh, from Bodman Industries, Aston, PA).
Mishra D., Wang S., Jin Z., Xin Y., Lochner E, & Mattoussi H. (2019). Highly Fluorescent Hybrid Au/Ag Nanoclusters Stabilized with Poly(ethylene glycol)- and Zwitterion-Modified Thiolate Ligands. Physical chemistry chemical physics : PCCP, 21(38), 21317-21328.
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6

Radical Polymerization of Functional Monomers

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Butyl 3-mercaptopropionate (BMP), 1-hexanethiol (HT), ethyl vinyl sulfone (EVS), 1-butyl acrylate (BA), N-propylmaleimide (PMI), diethyl maleate (DEM), diethyl fumarate (DEF), 4-hexen-3-one (HEO), and ethylene glycol diethyl ether (EGDE) were purchased from Sigma-Aldrich. All monomers were used as received. The photobase generator (PBG) NPPOC-TMG and hexyl vinyl sulfonate (HVS) were synthesized according to previous literature42 .
Huang S., Kim K., Musgrave G.M., Sharp M., Sinha J., Stansbury J.W., Musgrave C.B, & Bowman C.N. (2021). Determining Michael Acceptor Reactivity from Kinetic, Mechanistic, and Computational Analysis for the Base-catalyzed Thiol-Michael Reaction. Polymer chemistry, 12(25), 3619-3628.
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7

Synthesis of Colloidal Semiconductor Nanocrystals

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1-Octadecene (90%), oleic acid (90%), CdO
(≥99.99%), Se powder (100 mesh, 99.99%), trichloroethylene
(anhydrous, ≥99%), 1-hexanethiol (97%), and 1-octadecanethiol
(98%) were purchased from Sigma-Aldrich. 1-Decanethiol (96%) and 1-tetradecanethiol
(94%) were purchased from Alfa Aesar. 1H,1H,2H,2H-Perfluoro-1-hexanethiol
(97%) was purchased from Synquest Laboratories. Hydrochloric acid
(37%) and HPLC grade hexane were purchased from Bio-Lab.
Elimelech O., Oded M., Harries D, & Banin U. (2023). Spontaneous Patterning of Binary Ligand Mixtures on CdSe Nanocrystals: From Random to Janus Packing. ACS Nano, 17(6), 5852-5860.
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8

Functionalized Nanoparticle Synthesis Protocol

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Sodium citrate, hydrogen tetrachloroaurate trihydrate, sulfuric acid, ubiquinone-1, 1-mercaptohexanol (MCH), 1-hexanethiol (HT), mercaptohexanoic acid (MHA), mercaptoundecanoic acid (MUA), 3,3′-dithiodipropionic acid di(N-hydroxysuccinimide ester) (DTSP), dimethyl sulfoxide (DMSO), Nα′,Nα″-bis(carboxymethyl)-l-lysine, and nickel sulfate were purchased from Sigma (St-Louis, MO, USA); potassium phosphate dibasic trihydrate from Acros Organics (Geel, Belgium); mercaptopropionic acid and cysteamine (cyst) from Tokyo Chemical Industry (Tokyo, Japan). The 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) (sodium salt) (PG) and 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (PE) were provided by Avanti Polar Lipids Inc. (Alabaster, AL, USA). These chemicals were used without any additional purification. Thiols were dissolved in ethanol, and lipids were prepared in a 1/3 (v/v) mixture of ethanol and chloroform.
Nikolaev A., Makarchuk I., Thesseling A., Hoeser J., Friedrich T., Melin F, & Hellwig P. (2020). Stabilization of the Highly Hydrophobic Membrane Protein, Cytochrome bd Oxidase, on Metallic Surfaces for Direct Electrochemical Studies. Molecules, 25(14), 3240.
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9

Peptide Adsorption on Coated Surfaces

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GL13K (GKIIKLKASLKLL-NH2) was purchased from AAPPTec, LLC (Louisville, KY, USA) with purity >98%. HAP-coated (QSX327) and Au-coated (QSX301) QCM-D sensors were purchased from Biolin Scientific (Gothenburg, Sweden). 1-Hexanethiol (95%), 6-Mercaptohexanoic acid (90%), and 8-Amino-1-octanethiol hydrochloride (95%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). PBS at pH 7.4 (1X) was purchased from Thermo Fisher Scientific (Waltham, MA, USA).
Ye Z., Kobe A., Sang T, & Aparicio C. (2020). Unraveling dominant surface physicochemistry to build antimicrobial peptide coatings with supramolecular amphiphiles. Nanoscale, 12(40), 20767-20775.
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10

Synthesis of Colloidal Nanocrystals

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All chemicals, indium acetate (In(OAc)3, 99.99% trace metal basis, Sigma-Aldrich, St. Louis, MO, USA), zinc acetate (Zn(OAc)2, 99.99%, Sigma-Aldrich), lauric acid (98%, Sigma-Aldrich), myristic acid (99%, Sigma-Aldrich), stearic acid (99%, Sigma-Aldrich), oleic acid (90% technical grade Sigma-Aldrich), gallium trichloride (GaCl3 beads, anhydrous 99.999% trace metals basis, Sigma-Aldrich), 1-hexanethiol (95%, Sigma-Aldrich), 1-octanethiol (≥98.5%, Sigma-Aldrich), 1-dodecanethiol (≥98%, Sigma-Aldrich), 1-octadecene (ODE, 90% technical grade, Sigma-Aldrich), and tris(trimethylsilyl)phosphine ((TMS)3P, 10 wt% in hexane, SK Chemicals, Gyeonggi-do, Korea), were used without any further purification.
Lee W., Lee C., Kim B., Choi Y, & Chae H. (2020). Synthesis of Blue-Emissive InP/GaP/ZnS Quantum Dots via Controlling the Reaction Kinetics of Shell Growth and Length of Capping Ligands. Nanomaterials, 10(11), 2171.
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