Anthracene

Manufactured by Thermo Fisher Scientific

Sourced in United Kingdom

Anthracene is a crystalline solid organic compound. It is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. Anthracene is commonly used as a fluorescent material in various scientific and industrial applications.

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7,12-Dimethylbenz(a)anthracene (DMBA) (2 citations)

8 protocols using anthracene

Synthesis and Characterization of Pyrogallol[4]arene Compounds

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Reagents, solvents, guest molecules, and synthetic precursors were purchased from commercial suppliers at ACS Reagent Grade or equivalent purity and used without further purification. Pyrogallol, butrylaldehyde, anthracene, fluoranthene, pyrene, and fluorene were obtained from Acros Organics. Hydrochloric acid, ethanol, and methanol were obtained from Fisher Scientific. Undecanal and 1,5-diaminonaphthalene were obtained from TCI. Carbazole and coumarin were obtained from Sigma-Aldrich. 1-Adamantanecarboxylic acid and [2.2]paracyclophane were obtained from Alfa Aesar and Combi-blocks respectively. Deuterated solvents for NMR spectroscopy were purchased from Cambridge Isotopes. CDCl₃ was filtered through basic alumina prior to use. Pyrogallol[4]arenes 1a and 1b were synthesized using published procedures.26 ,32
¹H and ¹³C solution NMR spectra were acquired using a Bruker Avance IIIHD 600 MHz, a Varian Unity INOVA 500 MHz, or a Varian Mercury 400 MHz spectrometer. Residual solvent peaks were used as internal standards: CHCl₃ (δ^H = 7.26 ppm; δ^C = 77.16 ppm), benzene (δ^H = 7.16 ppm; δ^C = 128.06 ppm). NMR measurements performed in CCl₄ used a coaxial NMR tube insert and C₆D₆ for an external solvent lock and chemical shift referencing.

Journey S.N., Teppang K.L., Garcia C.A., Brim S.A., Onofrei D., Addison J.B., Holland G.P, & Purse B.W. (2017). Mechanically induced pyrogallol[4]arene hexamer assembly in the solid state extends the scope of molecular encapsulation †Electronic supplementary information (ESI) available: Experimental procedures, NMR spectra, and tabulated data. See DOI: 10.1039/c7sc03821f. Chemical Science, 8(11), 7737-7745.

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Soil Contamination by Model PAHs

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Four organic compounds, naphthalene (B&K Multi-branch Company), phenanthrene, anthracene, and pyrene (Acros Organics), were used as the model PAHs in the experiment. All of the tested compounds have been designated as priority pollutants by the US Environmental Protection Agency (US EPA). Soil samples were contaminated with powdered PAHs in the amount of 0, 1000, 2000, and 4000 mg kg⁻¹ dry matter of soil. The application of such high doses was justified by the amounts of PAHs that are released into the soil environment as a result of frequent and uncontrolled spills of petroleum derivatives (Park and Park 2011 (link)). Naphthalene, phenanthrene, anthracene, and pyrene are characterized by n-octanol/water partition coefficients of 3.6, 4.46, 4.5, and 4.8, respectively; they are insoluble in water, but soluble in organic compounds.

Lipińska A., Wyszkowska J, & Kucharski J. (2015). Diversity of organotrophic bacteria, activity of dehydrogenases and urease as well as seed germination and root growth Lepidium sativum, Sorghum saccharatum and Sinapis alba under the influence of polycyclic aromatic hydrocarbons. Environmental Science and Pollution Research International, 22(23), 18519-18530.

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Pulp-Based Biomaterial Synthesis

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Pulp was donated from Formosa Chemicals and Fiber Corp, Taiwan. APTES and 3,3',5,5'tetramethylbenzidine (TMB) were products from Alfa-Aesar, UK, and Dojindo, Japan, respectively. Doxorubicine•HCl and (3-(4,5-dimethylethiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) were purchased from Sigma-Aldrich, USA. Anthracene (99%), Nhydroxysuccinimide (NHS, 99%), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC, 98%), citric acid, FA, and ethylenediamine were purchased from Acros organics, UK. Other reagents were in commercial grade. Deionized and distilled water was obtained by purification in a Millipore purification system (Yamato Millipore WT100).

Do T.T.A., Grijalvo S., Imae T., Garcia-Celma M.J, & Rodríguez-Abreu C. (2021). A nanocellulose-based platform towards targeted chemo-photodynamic/photothermal cancer therapy. Carbohydrate polymers, 270.

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Fluoranthene, Anthracene, and Chitosan Protocol

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Reagents, Solvents, and Culture Media Fluoranthene (98%) was acquired from Sigma-Aldrich (Steinheim, Germany), anthracene (99%) was obtained from Acros Organics (New Jersey, USA) and chitosan (74% deacetylated) was obtained from Polymar (Fortaleza, Brazil). Salts, reagents, and solvents were obtained from Sigma-Aldrich (Steinheim, Germany) and Synth (São Paulo, Brazil). Whereas, agar and nutrient broth was purchased from Himedia Laboratories (Mumbai, India). The Taq DNA polymerase and others molecular supplies were obtained from Invitrogen (CA, USA) and Integrated DNA Technologies (IL, USA).

Garcia A.C.F.S., Araújo B.R., Birolli W.G., Marques C.G., Diniz L.E.C., Barbosa AM J.r., Porto A.L.M, & Romão L.P.C. (2019). Fluoranthene Biodegradation by Serratia sp. AC-11 Immobilized into Chitosan Beads. Applied biochemistry and biotechnology, 188(4).

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Synthesis and Characterization of Fluorescent Probes

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Anthracene and maleic anhydride
were purchased from Alfa Aesar (Lancashire, UK). Proline and ninhydrin
were purchased from Tokyo Chemical Industry (Tokyo, Japan). Potassium
bromide (KBr) IR grade, Nile red, 4-hydroxybenzoic acid, 7-amino-4-methylcoumarin,
terphenyl, and curcumin were purchased from Sigma-Aldrich (St. Louis,
MO, USA). Sodium hydroxide was purchased from SHOWA (Tokyo, Japan).
Toluene, acetone, hexane, and ethanol were purchased from Echo Chemical
(Taipei, Taiwan). Acetic acid was purchased from Aencore (Victoria,
Australia). Ethyl acetate was purchased from Seedchem (Melbourne,
Australia). These reagents were used as supplied unless otherwise
stated. Ultrapure water (>18.2 M Ω cm^–1) generated
from an ELGA PURELAB classic system (Taipei, Taiwan) was used in all
experiments. SYLGARD 184 silicone elastomer base and curing agent
were purchased from Dow Corning Corp. (Midland, MI, USA). Cy5 and
Cy3 tethered bicyclo[6.1.0]nonyne (BCN) and 2-[2-(2-azidoethoxy)ethoxy]ethanamine
click reagents were prepared by following a reported method and confirmed
by NMR spectroscopy.^{37 (link),38 (link)}

Yi S., Chen J.S., Wang C.M, & Liao W.S. (2021). Manipulating Chemical Processes by Pseudosolid Spatial Limitation. JACS Au, 1(9), 1435-1444.

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Synthesis of Triptycene and Pentiptycene Diols

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Triptycene-1,4-diol (TRP) (Wiegand et al., 2014 (link)) and pentiptycene-6,13-diol (PENT) (Luo et al., 2015 (link)) were synthesized according to previous literature. Anthracene, sodium hydrosulfite, 4,4′-dichlorodiphenylsulfone (DCDPS), and 4,4′-difluorodiphenylsulfone (DFDPS) were purchased from Alfa Aesar and used as received. 1,4-benzoquinone, tetrachloro-1,4-benzoquinone, potassium carbonate (K₂CO₃), sodium bicarbonate, acetic acid, methanol, and 2-propanol were purchased from Sigma-Aldrich. 4,4′-biphenol (BP) and 3,3′-disulfonated-4,4′-dichlorodiphenylsulfone (SDCDPS) were purchased from Akron Polymer Systems and dried in vacuum at 110°C for 24 h before use. Anhydrous N, N-dimethylacetamide (DMAc), toluene, and hydrogen peroxide (30 wt% solution) were purchased from EMD Millipore and used as received.

Wang T., Li T., Aboki J, & Guo R. (2020). Disulfonated Poly(arylene ether sulfone) Random Copolymers Containing Hierarchical Iptycene Units for Proton Exchange Membranes. Frontiers in Chemistry, 8, 674.

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Synthesis of Ligand An2Py

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Preparation of the ligand An2Py was according to reported procedures (see SI). Starting materials are purchased from Sigma Aldrich Chemicals unless otherwise stated. Perylene and anthracene were obtained from Alfa Aesar.

Quah H.S., Chen W., Schreyer M.K., Yang H., Wong M.W., Ji W, & Vittal J.J. (2015). Multiphoton harvesting metal–organic frameworks. Nature Communications, 6, 7954.

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Isolation and Characterization of Coal Tar Components

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Anthracene (>90%) was purchased
from Alfa Aesar and used as received. Nitrobenzene (99%) as an internal
standard was purchased from Fisher Scientific (New Jersey), toluene
(99.5%) was purchased from Caledon Laboratories Ltd. (Georgetown,
ON, Canada), acetonitrile (high-performance liquid chromatography
grade, 99.9%) was purchased from ACP Chemicals (Montreal, Canada),
and anhydrous ethanol was purchased from Commercial Alcohols (Brampton,
ON, Canada). All of these chemicals were used without further purification
except acetonitrile, which was dried over molecular sieves for 2 weeks.
Glacial acetic acid (>99.85%), magnesium powder (≤150 μm,
98% purity), magnesium turnings (∼4000 μm, 98% purity),
and graphite (99.99%) were purchased from Sigma-Aldrich, Canada. Coal
tar samples were collected from Sydney Tar Ponds, Nova Scotia, Canada,
according to the coal tar sampling methodology.³⁸

Al Shra’ah A., Georghiou P.E., Helleur R., MacQuarrie S.L., Zhao Y, & Mkandawire M. (2018). Optimizing Reductive Degradation of PAHs Using Anhydrous Ethanol with Magnesium Catalyzed by Glacial Acetic Acid. ACS Omega, 3(3), 3554-3561.

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