Tert butylmagnesium chloride

All reactions were conducted under argon atmosphere using standard Schlenk and glovebox techniques (<0.1 ppm O₂, <0.1 ppm H₂O). Toluene, benzene, n-hexane and n-pentane were degassed with nitrogen, dried over activated aluminium oxide (MBraun SPS) and stored over 3 Å molecular sieves. Deuterated solvents were dried over Na/K alloy and distilled under argon atmosphere, and a solution of tert-butylmagnesium chloride in Et₂O (Sigma-Aldrich) was used as receive. 2-[(2,3,4,5,6-Pentafluorophenyl)amino]-4[(2,3,4,5,6-pentafluorophenyl)imino]-pent-2-ene (^f5BDI-H) was synthesized according to the literature procedure^{57 (link)}. The oxygenation reactions were carried out using pure dioxygen dried by passing it through a tube filled with anhydrous NaOH/KOH. NMR spectra were acquired on Varian Inova 500 MHz and Varian Mercury 400 MHz spectrometer at 298 K. Elemental analysis were performed using an UNICUBE (Elementar Analysensysteme GmbH).

2,5-dibromo-3-hexylthiophene ≥97%, TCI (Tokyo, Japan), [1,3-bis(diphenylphosphino)-propane]dichloronickel(II) (Ni(dppp)Cl₂, ≥97% Sigma Aldrich, St. Louis, MO, USA), vinylmagnesium bromide (0.7 M solution in tetrahydrofuran, Acros Organics (Geel, Belgium)), tert-butylmagnesium chloride (2 M solution in diethyl ether, Sigma Aldrich), anhydrous tetrahydrofuran (99.9%, Acros organics) distilled before use, poly(methylhydrosiloxane) trimethylsilyl terminated (average M_n = 390, Sigma Aldrich (Saint Louis, MO, USA)), poly(ethylene glycol) methyl ether methacrylate (average M_n = 500, M_n = 950 and M_n = 300, Sigma Aldrich), poly(ethylene glycol) methacrylate (average M_n = 500, Sigma Aldrich), platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane (PTDD, Karstedt’s catalyst) (complex solution in xylene, Pt ~ 2%, Sigma Aldrich), anhydrous toluene (99.85%, Acros Organics).