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9 protocols using decahydronaphthalene

1

Fluorescent Probes for Oxidative Stress

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Tetraethyl orthosilicate (TEOS), triethanolamine (TEAH), coumarin (C9H6O2, 99%), 9,10-anthracenediyl-bis(methylene) dimalonic acid (ABDA), sodium dithionite (SDT) and decahydronaphthalene (98%) were purchased from Sigma-Aldrich. Potassium permanganate (97%) was obtained from Shanghai Chemical Co. Dichloromethane (99.99%) was purchased from Aladdin Industrial Inc. Dodecacarbonyltriiron (Fe3(CO)12, 96%) was purchased from Macklin Industrial Inc. All chemicals were used as received without any further purification. Hemoglobin (Hb) of bovine red blood cells was purchased from MP Biomedicals. DAPI, Lyso-Tracker Green, 2,7-dichlorodihydrofluorescein diacetate (DCFH-DA) and 2-[6-(4,-hydroxy)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid (HPF) were purchased from Beyotime Biotechnology.
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2

Colloidal Particle Tracking in Drying Droplets

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For direct tracking of individual particle motions with confocal laser microscopy, poly(methyl methacrylate) (PMMA) colloidal particles labeled with a fluorescent dye were used49 50 . As standard solvents for the colloidal droplets, a mixture of cis- and trans-decalin (Decahydronaphthalene, 99%, Sigma-Aldrich), were employed which has widely been used in drying experiments49 51 52 (link). Each droplet was gently deposited onto a clean cover glass (VWR, 22 × 30 mm2, No. 1.5) in all experiments. The initial drop volume was controlled to be V0 ≈ 0.5 μl, resulting in the initial contact radius of R0 ≈ 1.4 mm, which is smaller than the capillary length (≈1.9 mm for decalin): therefore, the droplet shape was assumed to be spherical. The PMMA colloids were prepared and supplied by A. Schofield (University of Edinburgh) according to the procedure described by Antl et al.53 , and thus were expected to show hard-sphere-like behaviors. The colloid radii were rS = 100 nm (small colloids) and rL = 1000 nm (large colloids) with ~5% polydispersity in size (previously determined by dynamic light scattering33 (link)). The density difference between colloids (1.19 g/cm3) and decalin (0.897 g/cm3) was small enough to prevent any sedimentation issues for the microscopic colloids54 .
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3

Synthesis of Mesoporous Silica Materials

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Cetyltrimethylammonium bromide (CTAB), cetyltrimethylammonium chloride (CTAC), PEO-PPO-PEO (P123), triethanolamine (TEA) and decahydronaphthalene (DHA) were purchased from Sigma-Aldrich (St. Louis, USA). Tetraethyl orthosilicate (TEOS) was provided by Aladdin Industrial Corporation (Shanghai, China); Sodium hydroxide, hydrochloric acid, acetonitrile, methanol, and anhydrous ethanol were purchased from Fuchen Chemicals Reagent Factory (Tianjin, China). The 1% (w/v) agarose gels, TBE buffer (Tris-boric acid-EDTA), and ethidium bromide (EB) were obtained from MultiSciences (Hangzhou, China).
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4

Synthesis and Characterization of Lipid Nanoparticles

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Hexadecyltrimethylammonium bromide (CTAB), decahydronaphthalene, 1-octadecene (ODE), PEI (branched, MW 1000), dipalmitoylphosphatidylcholine (DPPC), cholesterol, and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE)-PEG were provided by Sigma-Aldrich. NaOH, cyclohexane, NH4NO3, ammonia aqueous solution (28 wt%), tetraethyl orthosilicate (TEOS), (3-aminopropyl) triethoxysilane (APTES), triethanolamine (TEA), sodium 3-(trihydroxysilyl) propylmethylphosphonate (THPMP), and decahydronaphthalene (98%) were obtained from Macklin Industrial, Inc. LNPs were purchased from Jiliang Pharmaceutical Engineering Co., Ltd. (Shanghai).
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5

Maleated EPM Crosslinked with CNT

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A maleated EPM (EPM-g-MA, Keltan DE5005, 49 wt % ethylene, 2.1 wt % MA, Mn = 50 kg/mol, polydispersity index = 2.0) were kindly provided by ARLANXEO Performance Elastomers. Furfurylamine (FFA, Sigma-Aldrich, St. Louis, MO, USA, ≥99%) was freshly distillated. Multi-walled carbon nanotubes (CNT, Sigma-Aldrich, diameter × L 6–9 nm × 5 µm, >95% (carbon)) were used as additive and cross-linking agent. 1,1′-methylenedi-4,1-phenylene)bismaleimide (BM, Sigma-Aldrich, ≥97%) and dicumyl peroxide (DCP, Sigma-Aldrich, 98%) were used as reversible and irreversible cross-linking agents, respectively. 3-azido-1-propanamine (90%), octadecyl-1-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate (anti-oxidant, 99%), 1-methyl-2-pyrrolidinone (NMP, 99.5%), tetrahydrofuran (THF, >99.9%), decahydro naphthalene (decalin, mixture of cis + trans, >98%) and acetone (>99.5%) were all bought from Sigma-Aldrich and used as received.
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6

Polymer Nanocomposite Fabrication and Characterization

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Low-density polyethylene (LDPE, EM460, with melt flow index of 27 g per 10 min; density 0.918 g·cm−3) was provided by Westlake Polymers Corporation (Houston, TX, USA, October 2018). Single-walled carbon nanotubes (SWCNTs) of outer diameter 2 nm and graphene oxide (GO) were obtained from Cheap Tubes Inc, Cambridge, MA, USA. GO had lateral dimension of 300–800 nm, with a thickness of 0.7–1.2 nm, and 99% purity, as per the supplier (Sigma-Aldrich, St. Louis, MO, USA). Natural clay (Montmorillonite SiO2/Al2O3), nanoclays (surface modified with 25–30 wt.% trimethyl stearyl ammonium), and decahydronaphthalene were obtained from Sigma-Aldrich, St. Louis, MO, USA. The BET specific surface area (m2·g−1) of CNTs, graphene oxide, clay, and modified clay were 407, 350, 250, and 750, respectively.
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7

Synthesis and Characterization of PFO Polymer

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PFO, synthesized by Suzuki coupling, was supplied by Cambridge Display Technology and used as received. The polymer had a number‐average molecular weight
Mn = 18 × 103 g mol−1 and a polydispersity index = 2.7, as determined by polystyrene‐equivalent gel permeation chromatography. The absolute molecular weight was calculated by scaling
Mn down by a factor of 2.7 due to the higher relative chain stiffness of PFO,17 giving an estimate of 17 fluorene repeat units per average chain. Toluene (HPLC grade, >99.7%, VWR), decahydronaphthalene (“decalin”; reagent grade, mixture of cis and trans isomers, Sigma‐Aldrich), cyclohexane (HPLC grade, >99%, VWR), and 2‐(iso‐)propanol (“IPA”; >99.5%, Sigma‐Aldrich) were used as received.
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8

Synthesis of Polymethacrylate Microspheres

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Pyromellitic dianhydride (PMDA, 97%), 4,4′-oxydianiline (ODA, 97%), 1-methyl-2-pyrrolidone (NMP, 99%), n-hexadecane (99%), pyridine (99%), acetic anhydride (Ac2O, 99%), and decahydronaphthalene (mixture of cis and trans forms, decalin, 99%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). All water was double-distilled. Methyl methacrylate (MMA, 99%) and divinylbenzene (DVB, 80%) were also purchased from Sigma-Aldrich and used as shell materials. 2,2′-Azobis(2-methylpropionitrile) (AIBN, 98%) was purchased from Sigma-Aldrich and was used as a radical initiator for the polymerization of MMA and DVB. Sulfuric acid (95%~98%) was purchased from Sigma-Aldrich and was used for viscosity measurements. Acetone (>99%) and methanol (>99%) were purchased from SK Chemicals (Seongnam, Korea).
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9

Synthesis and Characterization of Functional Nanomaterials

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Hexadecyltrimethylammonium bromide (CTAB, ≥99%), paraffin wax (mp ≥65 °C), (3-aminopropyl)triethoxysilane (APTES) (99%), palladium(II) nitrate dihydrate, benzaldehyde (≥99%), benzyl alcohol (99.8%), vanillyl alcohol (≥98%), 2-methoxy-4-methyl-phenol (p-creosol, ≥98%), toluene ≥99.5%), decahydronaphthalene(decalin, mixture of cis +trans, ≥99%), heptadecane (99%), dodecane (≥99%), and Sudan III were purchased from Sigma-Aldrich. Isooctane (99%) and high-performance liquid chromatography (HPLC)-grade water (≥99.9%) were purchased from Fisher Scientific. Chloroform (≥99.8%, Macron), methanol (≥99.8%, VWR), ammonium hydroxide (70% w/w, PubChem), silica spheres (500 nm diameter, non-porous, SA 6.02 ± 0.07 m 2 /g, Alfa Aesar), and Methyl Blue (MP Biomedicals) were purchased from suppliers as indicated. Prepurified nitrogen and ultra-high-purity H 2 were obtained from Airgas.
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