Fresh silica was loaded onto a 21 cm wide Büchner funnel with a frit to form a layer approximately 6 cm thick. The silica containing the evaporated reaction mixture was loaded on top of this layer and washed with CH 2 Cl 2 until colorless. The purple eluate was collected and concentrated under reduced pressure. Hexane (300 mL) was added to the concentrated solution (100 mL) of the product and left to crystallize overnight. The resulting deep purple crystals were collected by filtration, washed with hexanes, and dried under reduced pressure to yield between 0.8 and 1.2 g of product (10-15 % yield). Crystals suitable for single-crystal X-ray diffraction were isolated by slow diffusion of hexane vapors into a saturated solution of the compound in CH 2 Cl 2 . 1 H NMR (CD 2 Cl 2 ) d (ppm) -3.36 (s, 2H), 0.95 (t, 7.2 Hz, 12H), 1.38-1.54 (m, 16H), 1.66-1.74 (m, 8H), 2.16 (dq, 7.9, 6.8 Hz, 8H), 5.06 (t, 6.8 Hz, 8H), 9.55(s, 8H). Porphine (2). The product of the previous step (3, 500 mg) was dissolved in a mixture of THF and methanol (130 + 110 mL). KOH (5 g) dissolved in distilled water (50 mL) was added to the solution and the mixture was refluxed overnight. The color of the reaction mixture changed from deep purple-brown to reddish-violet. The reaction mixture was cooled to room temperature and neutralized with 10% HCl (40 mL). The solution was decanted and evaporated to dryness. To the dried residue, H 3 PO 4 (80 mL) followed by P 4 O 10 (5 g) were added, the flask was flushed with argon and heated to 200 °C for 4 h. The originally deep green solution changed to intense purple color. After cooling to room temperature, the mixture was carefully poured to a solution of Na 2 CO 3 (120 g) in water (500 mL) in a 2 L Erlenmeyer flask. The brownish slurry was subsequently extracted with CHCl 3 (1 L), the extract was dried with Na 2 SO 4 and evaporated to dryness to yield copper-colored powder (180 mg, 95 % yield). H NMR (DMSO-d 6 ) d (ppm) -4.16 (s, 2H), 9.76 (s, 4H), 10.64 (s, 8H). C NMR (DMSO-d 6 ) d (ppm) 131.98, 104.24 (the third expected signal was not observed). Magnesium(II) Porphyrin (Mg-2). Porphine (2, 105 mg) was suspended in dry pyridine (50 mL) and magnesium hydride (500 mg) was added. The reaction mixture was refluxed at 140 °C under inert atmosphere for three days. The liquids were evaporated in vacuum, the solid residue was purified by column chromatography using a short column (~ 5 cm) of neutral alumina, and the product was eluted with a tetrahydrofuran/hexane (1 : 2) mixture. The pink fractions were evaporated, the residual solid was suspended in pentane, filtered and air-dried to yield 141 mg of a purple powder (85 %). H NMR (acetone-d 6 ) d (ppm) 9.59 (s, 8 H), 10.42 (s, 4H). C NMR (acetone-d 6 ) d (ppm) 150.4, 132.9, 106.2. Zinc(II) Porphyrin (Zn-2). Porphine (2, 115 mg) and zinc(II) acetate (200 mg) were dissolved in freshly distilled benzonitrile (20 mL) and heated under argon atmosphere at 190 °C for 1 h. After cooling to room temperature, the reaction mixture was poured onto a short neutral alumina column and washed with dichloromethane to remove benzonitrile. The product was eluted with tetrahydrofuran. Purple crystals of the product precipitated upon concentration of the tetrahydrofuran solution under reduced pressure. The crystals were filtered, washed with a small amount of pentane and dried to yield 138 mg of the product (quant.). H NMR (tetrahydrofuran-d 8 ) d (ppm) 9.55 (s, 8H), 10.34 (s, 4H). Copper(II) Porphyrin (Cu-2). Porphine (2, 30 mg), copper(II) acetate (60 mg) and dry benzonitrile (20 mL) were heated under argon atmosphere with exclusion of light at 180 °C for