Compound 15
ladder macrocycle
From: Dynamic self-correcting nucleophilic aromatic substitution
View in PubChem | MDL Molfile | Chemdraw file
Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a sealed tube with a stirrer bar containing K2CO3 (83 mg, 0.60 mmol), 2-(2,6-diisopropylphenyl)-4,5,6,7-tetrafluoroisoindoline-1,3-dione (37.9 mg, 0.10 mmol) and 1,2,4,5-benzenetetrathiol (20.6 mg, 0.10 mmol) under argon was added THF (0.5 mL) and DMF (0.5 mL). The reaction was stirred at room temperature for 2 days or at 50 oC for 1 day. The mixture was concentrated and precipitated into an aqueous 1 M HCl solution. The precipitate was filtered and washed with water, methanol, hexane, acetone and ethyl acetate to obtain an orange solid (48.0 mg, 95%). Alternatively, the reaction can also be performed under high dilution conditions using THF (10 mL) and DMF (10 mL) at room temperature for 5 days or at 50 oC for 2 days to obtain the product in comparable yield. 1H NMR (500 MHz, TCE-d2) δ 7.79–7.69 (m, 2H), 7.47 (br, 1H), 7.28 (br, 2H), 2.60 (br, 2H), 1.14 (br, 12H) for repeat unit. 13C NMR (126 MHz, TCE-d2) δ 165.2, 146.9, 140.8, 133.9, 133.5, 133.0, 130.3, 128.6 (br), 126.5, 126.1, 123.9, 29.2, 24.0 for repeat unit.
