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4 protocols using tetrabromomethane

1

Synthesis of Enriched Silica and Titania Nanoparticles

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SiO2 (Aerosil 200, Degussa, 180 m2/g, aggregated nanoparticles of ~12 nm diameter) and TiO2 (St-Gobain Norpro, anatase phase, 150 m2/g) were used as main oxide precursors. The porous TiO2 precursor, initially in the form of cylindrical monoliths (~1 cm long, ~0.3 mm diameter), was pre-ground into a fine powder using an agate mortar and pestle before use. A quartz phase (BCR-066; particle size: 0.35 – 3.5 μm) was also enriched once in 17O for comparison to Aerosil (Figure S2b). 17O-enriched water was purchased from CortecNet. The isotope composition of this water is ~ 90.4 % of 17O. TEKPol and d2-tetrachloroethane were purchased from Cortecnet. Tetrabromomethane was purchased from Sigma-Aldrich.
Ball milling experiments were carried out either using a Retsch Mixer Mill 400 (MM400) apparatus or a Fritsch P23 vertical mixer mill. For the P23 mixer mill, the hardened stainless steel jar and balls were used. For the MM 400 mixer mill, the stainless steel jar with a screw-top lid (used in LAG) or push-fit lid (used in dry milling) and balls were used.
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2

Synthesis of Carbohydrate Derivatives

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Methyl α-d-glucopyranoside (≥99%), tetrabromomethane (99%), triphenylphosphine (99%), anhydrous pyridine (99.8%), sodium dicyanamide (96%), trimethylamine 31–35 wt.% in ethanol solution, and Ludox® HS-40 colloidal silica (40 wt.% suspension in H2O) were commercial materials purchased from Sigma-Aldrich. Potassium tricyanomethanide (98%) and potassium tetracyanoborate (97%) were acquired from Strem, Newburyport, MA, USA and SelectLab Chemicals, Münster, Germany respectively. Silver nitrate (99.9%) was received from POCH, Gliwice, Poland. N-(6-Deoxy-1-O-methoxy-α-d-glucopyranoside)-N,N,N-trimethylammonium bromide was synthesized according to a previously described procedure [5 (link)].
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3

Solid-State NMR Characterization of Oxides

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Reagents and equipment: SiO2 (Aerosil 200, Degussa, 180 m2/g, aggregated nanoparticles of ≈12 nm diameter) and TiO2 (St‐Gobain Norpro, anatase phase, 150 m2/g) were used as main oxide precursors. The porous TiO2 precursor, initially in the form of cylindrical monoliths (≈1 cm long, ≈0.3 cm diameter), was pre‐ground into a fine powder using an agate mortar and pestle before use. A quartz phase (BCR‐066; particle size: 0.35–3.5 μm) was also enriched once in 17O for comparison to Aerosil (Figure S2b). 17O‐enriched water was purchased from CortecNet. The isotope composition of this water is ≈90.4 % of 17O. TEKPol and d2‐tetrachloroethane were purchased from Cortecnet. Tetrabromomethane was purchased from Sigma‐Aldrich.
Ball milling experiments were carried out either using a Retsch Mixer Mill 400 (MM400) apparatus or a Fritsch P23 vertical mixer mill. For the P23 mixer mill, the hardened stainless steel jar and balls were used. For the MM 400 mixer mill, the stainless steel jar with a screw‐top lid (used in LAG) or push‐fit lid (used in dry milling) and stainless steel balls were used.
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4

Synthesis and Characterization of C60 Derivatives

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C60 fullerene, 8-bromo-1-octanol, malonyl chloride, 4-hydroxy-TEMPO, iodine, 9,10-dimethylanthracene (DMA), tetrabromomethane, benzyl alcohol, 4-methoxybenzyl alcohol, cyclohexanol, allyl alcohol, diphenylmethanol, 1-phenylethanol, toluene, and n-hexane were purchased from Sigma-Aldrich. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), ethyl malonyl chloride, potassium thioacetate, silica gel 70–230 mesh, and gold powder spherical 0.5–0.8 μm S.A. 0.45–0.7 m2/g were obtained from Alfa Aesar. Sodium sulfate, acetonitrile, triethylamine, methylene chloride, dimethylformamide, and ethyl acetate were purchased from POCh (Poland). Methylene chloride, dimethylformamide, and toluene were dried and purified before use according to standard procedures. Other solvents were HPLC or analytical grade reagents and were used as received.
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