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3 protocols using formaldehyde dimethyl acetal

1

Triptycene Synthesis and Characterization

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All purchased chemicals were at least reagent grade and were used without further purification. Triptycene (98.0%), anhydrous ferric chloride (FeCl3, ≥98.0%), 1,2-dichloroethane (DCE, 99.8%), and formaldehyde dimethyl acetal (FDA, ≥98.0%) were purchased from Sigma-Aldrich. Crown-ether-15 (98.0%) and all other solvents were purchased from TCI America. Deionized water was used to prepare all aqueous solutions.
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2

Synthesis and Characterization of Dye Compounds

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All of the purchased chemicals were of at least reagent grade and were used without further purification. Triptycene (98.0%), anhydrous ferric chloride (FeCl3, ≥98.0%), 1,2-dichloroethane (DCE, 99.8%), formaldehyde dimethyl acetal (FDA, ≥98.0%), and chlorosulfonic acid (ClSO3H, 99%) were purchased from Sigma-Aldrich. All of the other solvents were purchased from TCI America. The methylene blue (MEB, 99%), basic fuchsin (BF, 98%), and malachite green (MG, 98%), were purchased from Macklin Biochemical Co. Ltd. (Shanghai, China), and the above three dyes were used without further purification. Their structures are shown in Fig. 1.
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3

Palladium-Catalyzed Bromination of Anisole

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4-Bromoanisole phenylboronic acid (PBA, 95%), biphenyl (BP, 99.5%), N,N-dimethylformamide (DMF, 99.8%), diphenylamine (DPA, 99%), formaldehyde dimethylacetal (dimethoxymethane, methylal, 99%), methanol (MeOH, 99.8%), naphthalene (NA, 99%), 1-naphthol (NL, ≥99%), nitric acid (HNO3, 70%), sulfuric acid (H2SO4, 96%), tetrahydrofuran (THF, ≥99.9%), ethanol (EtOH, ≥99.8%), isopropanol (i-PrOH, ≥99.5%), FeCl3 (anhydrous, ≥99.99%), and sodium hydroxide (NaOH, ≥98%) were purchased from Sigma-Aldrich, St. Louis, MO, USA. 1,2-Dichloroethan (1,2-DCE, 99.9%) was purchased from JSC “1 Base Chemical Reagents” (Staraya Kupavna, Russia). Palladium acetate (Pd(CH3COO)2, 47.68%ofPd) were obtained from JSC “Aurat”, Moscow, Russia. All chemicals were used as received. Distilled water was purified with an Elsi-Aqua water purification system.
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