*4.1. General Methods and Procedures*

The reagents phthalonitrile (TCI, Philadelphia, PA, USA), trimethylsilyl trifluoromethanesulfonate (Synquest, Alachua, FL, USA), chlorotrimethylsilane (Acros, Fair Lawn, NJ, USA), silicon tetrachloride (Sigma, Sheboygan, WI, USA) and 1,3-diiminoisoindoline (TCI, Philadelphia, PA, USA) were obtained commercially and used as received. Lithium bis(trimethylsilylamide) etherate [30], HCl gas [31] and bis(3,4,5-trifluorophenoxy) silicon phthalocyanine [32] were prepared as outlined in literature. All solvents were ACS grade; dry solvents were obtained by passing through activated alumina on a J.C. Meyer solvent purification system. Quinoline (Oakwood, Estill, SC, USA) was distilled over zinc dust. All reactions were performed under an atmosphere of dry nitrogen. NMR spectra were run in either DMSO-d6 or MeCN-d3 solutions at room temperature on a Bruker Avance 300 or 400 MHz spectrometer (Billerica, MA, USA, Figures S2–S4). 19F-NMR spectra were referenced to trifluoroacetic acid at −76.55 ppm (Figure S5). IR spectra of solid samples were recorded on an Agilent Technologies Cary 630 FT-IR spectrometer (Cary, NC, USA).
