Azobisisobutyronitrile

TIBA (1 M solution in hexane, Merck, NJ, USA), MMAO-12 (1.52 M solution in Toluene, Merck, NJ, USA), azobisisobutyronitrile (AIBN, Merck, NJ, USA), benzoyl peroxide (Merck, NJ, USA), mesitylene (Merck, NJ, USA) and CDCl₃ (99.8% ²H, Cambridge Isotope Laboratories, Inc., MS, USA) were used as purchased. Toluene (Merck, NJ, USA) was refluxed over sodium and stored under argon atmosphere. Maleic anhydride (MA, Merck, NJ, USA) was recrystallized from Toluene before use. Hex-1-ene (Merck, NJ, USA) was stored over Na wire and distilled under argon. The ¹H NMR spectra were recorded on a Bruker AVANCE 400 spectrometer (400 MHz, Bruker, MS, USA) at 20 °C. The chemical shifts are reported in ppm relative to the solvent residual peaks.
Zirconium complex 1 was prepared in accordance with published procedure [81 (link)]. Dimerization of hex-1-ene was conducted in liquid olefin media in the presence of 1, activated by TIBA and MMAO-12 using the protocol described previously [47 (link),49 (link)], 5-methyleneundecane was separated by the vacuum distillation, b. p. 80 °C at 7 Torr.

All chemicals and reagents used were of analytical reagent grade, and double distilled water was used in the preparation of all solutions. 1-allyl-3-methylimidazolim bromide was purchased from Chemistry and chemical engineering research center (Karaj, Iran,). Azobisisobutyronitrile (AIBN), ethylene glycol dimethylacrylate (EGDMA), acetonitrile, sulfanilic acid, N-(1-Naphthyl) ethylene diamine (NED), ammonium ferric sulfate, ammonium ferrous sulfate, nitric acid, zinc powder, ammonium hydroxide and, hydrochloric acid were purchased from Merck (Darmstadt, Germany). Standard solutions were prepared by dissolving the appropriate amount of sodium nitrite and sodium nitrate in water and diluting to 100 mL. NED (0.1 g in 100 mL water) and sulfanilic acid (1 g in 100 mL phosphoric acid 5%) were used and stored in the darkness at 4 °C. The pH of solutions was adjusted by 0.5 mol L⁻¹ NaOH and HCl solution.

The reagents utilized for silica colloid synthesis, including tetraethyl orthosilicate (≥99 wt.%), ethanol (200 proof), and aqueous ammonium hydroxide (30–33 wt.%), are provided by Merck KGaA. Ethoxylated trimethylolpropane triacrylate (ETPTA, SR-454) monomers and 2-hydroxyethyl methacrylate (HEMA) (≥99 wt.%) monomers are acquired from Sartomer Americas and Merck KGaA, respectively. Initiators, 2-hydroxy-2-methyl-1-phenyl-1-propanone (97 wt.%) and azobisisobutyronitrile (98 wt.%) are purchased from Merck KGaA. Aqueous hydrofluoric acid (≥48 vol.%), used to wet etch silica colloids, is collected from Merck KGaA. All chemicals and solvents are of analytical reagent quality and applied directly without any purification. Ultrapure water is obtained from a LABSTAC WU113 laboratory ultrapure water system. The unripe muskmelons with green rinds, tough blossom-ends, and stems still attached, are picked and provided by Taiwan Fresh Fruit Marketing Cooperative.

Cu(NO₃)₂ (99.99%), Fe(NO₃)₃ (98%), NaOH (98%) solution, acetone (99.5%), and chloroform (99%) were obtained from Merck company and utilized without further purification. For the synthesis of graphene quantum dots, citric acid monohydrate (Merck, 98%) was used. Pirimicarb was ordered from Mahan Co. (Tabriz, Iran). Ethylene glycol dimethacrylate (EGDMA) (97.5%) and Methacrylic acid (MAA) (99.6%) were acquired from Sigma-Aldrich, and Azobisisobutyronitrile (AIBN) (96%) was purchased from Merck.

All chemicals used were of analytical grade. Graphite flakes, acetic acid (99.7%), sulphuric acid (97.0%), sodium hydroxide (98%), acetone (99.5%), KMnO₄ (99.0%), NaNO₃ (99.0%), H₂O₂ (30%), and methanol (99.9%) were purchased from Sigma Aldrich USA. Itaconic acid (99%), azobisisobutyronitrile (98%), standard of coenzyme Q10 (98%), fluorene (98%), acetonitrile (99.8%), n-hexane (97.0%), 2-propanol (%), ethanol (96%), NaCl (99.5%), ascorbic acid (99.0%), tetrahydrofuran (THF) (99.9%), and phosphoric acid (85%) were bought from MERCK Germany. All of the experimental solutions were made with deionized (DI) water.