Synthesis and Characterization of Schiff Base 1

All chemicals used were of the highest grade available and were used as received. Schiff base 1 was synthesized based on a previous report.⁵¹ The tris(2,4-dibromophenyl)aminium hexafluoroantimonate oxidant (N(C₆H₃Br₂)₃SbF₆, E_1/2 = 1.14 V vs. Fc/Fc⁺ in MeCN)^{52,53 (link)} was prepared from commercially available triphenylamine by reported procedures.^{17,54 (link)1}H and ¹³C NMR spectra were collected at Trinity Western University on a Bruker ASCEND III 400 MHz with Bruker AVANCE III 400 MHz instrument running the TopSpin 3.1.6 program. Mass spectrometry data (electrospray ionization (ESI) positive ion or ESI negative ion) were collected at Simon Fraser University on an Agilent 6210 TOF ESI-MS instrument. Elemental analyses (C, H, N) were performed at the University of British Columbia on a Thermo Flash 2000 elemental analyzer. Electronic spectra were collected on a Cary 50 spectrophotometer using a custom designed immersion fiber-optic probe with a path length of 1 mm (Hellma Inc.). Temperatures were maintained during data collection using a dry ice/acetone bath (−78 °C). Cyclic voltammetry (CV) data were collected on a CHI-630E potentiostat connected to a three electrode voltammetry cell (Ag/AgCl wire reference electrode, glassy carbon working electrode, and a Pt auxiliary electrode) with tetra-n-butylammnoiumperchlorate (ⁿBu₄NClO₄, 0.1 M) as supporting electrolyte. Cobaltaceniumhexafluorophosphate (E_1/2 = −1.34 V vs. Fc/Fc⁺ in 0.1 M ⁿBu₄NClO₄ in CH₂Cl₂) were used as internal standards.