Synthesis and Characterization of Cyanobenzene Derivatives

All the synthesis chemicals and reactants such as 1,4-dicyanobenzene $({\mathrm{C}}_6{\mathrm{H}}_4{\left(\mathrm{C}\mathrm{N}\right)}_2$ ) (Sigma-Aldrich, Burlington, Massachusetts, MA, USA), sodium azide ( $\mathrm{N}\mathrm{a}{\mathrm{N}}_3$ ) (Sigma-Aldrich), zinc chloride (NaCl), nitric acid, 70% ACS ( $\mathrm{H}\mathrm{N}{\mathrm{O}}_3$ ) (Fermont), nickel (II) chloride hexahydrate ( $\mathrm{N}\mathrm{i}\mathrm{C}{\mathrm{l}}_2·6{\mathrm{H}}_2\mathrm{O}$ ), tetrabutylammonium hydroxide solution (HT), technical, ~40% in ${\mathrm{H}}_2\mathrm{O}$ (~1.5 M) (Sigma-Aldrich), ethanol, etc. and reagents for electrochemical analysis such as poly(vinylidene fluoride) (PVDF) (Sigma-Aldrich), 1-methyl-2-pyrrolidine (NMP) (Sigma-Aldrich), potassium hydroxide (KOH) (EMSURE^®, Darmstadt, Germany), activated charcoal (AC) (Supelco Analytical, St. Louis, SL, United States.), and conductive silver printing ink (Sigma-Aldrich) were purchased from different companies and utilized, without any further purifications.