Compound 1

1,1,2,2-tetrakis(4-aminophenyl)ethene

From: Molecular docking sites designed for the generation of highly crystalline covalent organic frameworks

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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Under nitrogen, compound 4 (1.00 g, 1.95 mmol) was dissolved in 20 mL of THF. Raney Nickel (ca. 4 g) and hydrazine monohydrate (1.30 mL, 26.7 mmol) were added to the solution and the mixture was refluxed for 2 h. The solution was allowed to cool to 55 °C and the Raney Nickel was filtered off. All volatiles were evaporated under reduced pressure, yielding the title compound (0.75 g, 1.92 mmol, 98 %) as a yellow powder. 1H NMR (400 MHz, DMSO-d6): 6.57 (d, J = 8.00 Hz, 8 H), 6.26 (d, J = 8.00 Hz, 8 H), 4.85 (s, 8 H).

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