Sodium nitrate

Graphite powder purchased from Sigma‐Aldrich (St. Louis, MO, USA). Sodium borohydride (NaBH₄), Sodium nitrate (NaNO₃), Hydrogen peroxide (H₂O₂), Sulfuric acid (H₂SO₄), Methylene blue (MB), and Sodium Hydroxide (NaOH) were purchased from Kanto Chemical Co. Inc. (Tokyo, Japan). Potassium permanganate (KMnO₄) was obtained from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan). All of the reagents were of analytical grade and were used directly without further purification.

2,2-Bis(4-aminophenyl)hexafluoropropane (>98.0%), 4-chlorobenzyl bromide (>95.0%), phenylacetonitrile (>98.0%), sodium hydride (60% dispersion in paraffin liquid), tetrahydrofuran anhydrous (stabilized with 2,6-di-tert-butyl-4-methylphenol, >99.5%), diethyl ether anhydrous (stabilized with 2,6-di-tert-butyl-4-methylphenol, >99.5%), cesium carbonate (>98.0%), iodomethane (>98.5%), and 2,2′-bipyridyl (bpy, >99%) were purchased from Tokyo Chemical Industry Co., Ltd, and used as received. Hydrochloric acid (35.0–37.0%), potassium hydroxide (>86%), sodium chloride (99%), sodium carbonate (>99.8%), sodium thiosulfate (>99.0%), sodium nitrate (>99%), sodium hydrogen carbonate (>99.5%), sodium nitrite (>98.5%), silver nitrate aq. (0.01 M), dimethyl sulfoxide (DMSO, >99%), bis(1,5-cyclooctadiene)nickel(0) (Ni(COD)₂, 95%), N,N-dimethylacetamide (>99%), hexane (>96%), dichloromethane (DCM, >99.5%), silica gel N60 (spherical, neutral, 100–210 μm), sodium sulfate (>98.5%), magnesium sulfate, anhydrous (>95.0%), diethyl ether (>99.0%) and lithium aluminum hydride (LAH, >92.0%) were purchased from Kanto Chemical Co., Inc., and used as received. Dimethylsulfoxide-d₆ with 0.03% TMS (DMSO-d₆, Acros Organics) and chloroform-d₁ (CDCl₃, Acros Organics) were used as received.