Compound FSA

3,9-diamino-benzo[1,2-b:4,5-b’]bis[1]benzothiophene-5,5,11,11-tetraoxide

From: Sulfone-containing covalent organic frameworks for photocatalytic hydrogen evolution from water

View in PubChem | MDL Molfile | Chemdraw file.

Synonyms:
  • 3,9-diamino-benzo[1,2-b:4,5-b’]bis[1]benzothiophene sulfone

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: Crystallographic data

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

4, 4’-Diamino- p-terphenyl (2.6 g, 10 mmol) was taken up in sulfuric acid (10 mL, 30% free SO3) and the resulting purple solution was heated to 80 °C overnight with stirring to give a black mixture. After cooling to room temperature, the solution was poured into water, and the solids were filtered off and neutralized with saturated sodium bicarbonate solution. The crude product was purified by Soxhlet extraction with acetone. After drying at 80 °C, the product was obtained as an orange solid (1.5 g, 39%). 1H NMR (400 MHz, DMSO-d6) δ [ppm]: 8.46 (s, 2H), 7.93 (d, J = 8.4 Hz, 2H), 6.98 (d, J = 2.0 Hz, 2H), 6.90 – 6.87 (m, 2H), 6.26 (s, 4H). 13C{ 1H} NMR (100 MHz, DMSO-d6) δ [ppm]: 152.4, 141.5, 139.1, 132.6, 124.7, 118.9, 116.6, 114.8, 105.5. HR-MS (CI, CH4): m/z calcd for C18H12N2O4S2: 385.0311 (M)+; found, 385.0293. Anal. Calcd for C18H12N2O4S2: C, 56.24; H, 3.15; N, 7.29; S, 16.68. Found: C, 50.04; H, 2.99; N, 6.06; S, 16.52.