Compound OP8NO2
α,ω-Bis(4,5-dimethoxy-2-nitrophenyl)-hexa(4,5-dimethoxy-1,2-phenylene)
From: Redox-responsive molecular helices with highly condensed π-clouds
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InChIKey VMDUFGBGDGXXRM-UHFFFAOYSA-N
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Nitric acid (500 µL, 7.8 mmol, density 1.42) was added at –20 °C to a CHCl3 solution (40 mL) of OP8H (200 mg, 0.18 mmol), and the mixture was stirred at the same temperature for 1 hour and then at 25 °C for 1.5 hours. The reaction mixture was diluted with CHCl3, washed successively with a saturated aqueous solution of NaHCO3 and water, dried over anhydrous MgSO4, and filtered off from an insoluble fraction. The filtrate was evaporated to dryness under a reduced pressure, and the residue was subjected to column chromatography (SiO2, AcOEt), to allow isolation of OP8NO as yellow solid (150 mg, 0.13 mmol) in 69% yield. IR (KBr): νmax (cm–1) 2936, 1604, 1513, 1337, 1250, 1027, 864, 778. 1H NMR (500 MHz, CDCl3): δ (ppm) 7.55–4.25 (m, 16H), 4.20–2.70 (m, 48H). MALDI-TOF mass: calcd. for C64H64N2O20 [M]+: m/z = 1180.41; found: 1180.54. Anal. calcd. for C64H64N2O20•2H2O: C, 63.15; H, 5.63; N, 2.30. Found: C, 63.10; H, 5.68; N, 2.34.
