Compound 3

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Compound data: CIF

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

[c4]DC 3: a solution of Zn(ClO₄)₂ (136 mg, 0.365 mmol) in MeCN (0.5 mL) was added to a solution of the monomer 1 (252 mg, 0.363 mmol) in MeCN (36 mL) and then the mixture was heated at 50 °C for 16 h. The isocyanate 2 (0.157 mL, 0.909 mmol) was added and then the mixture was stirred at room temperature for 16 h. After the addition of a solution of Na₄EDTA (6.94 g, 18.3 mmol) in H₂O (36 mL), the mixture was stirred at room temperature for 1 h. The organic solvent was evaporated under reduced pressure and the residue partitioned between CH₂Cl₂ (3 × 80 mL) and water (150 mL). The combined organic phases were dried (MgSO₄) and concentrated; the residue was purified chromatographically [NH-silica gel; EtOAc/hexanes (4:6) then CH₂Cl₂], followed by reprecipitation from CH₂Cl₂/hexanes, to afford 3 as a green-yellow solid (221 mg, 64%). M.p. 205–206 °C; ¹H NMR (400 MHz, CD₂Cl₂): δ = 3.56–3.74 (m, 32H), 4.25 (d, J = 10.8 Hz, 8H), 4.36 (d, J = 10.8 Hz, 8H), 4.49–4.65 (m, 32H), 6.67 (d, J = 7.6 Hz, 8H), 6.92–7.05 (m, 40H), 7.32 (s, 4H), 7.44 (s, 4H), 7.53 (s, 4H), 7.60 (s, 8H), 7.78 (s, 8H), 7.80 (dd, J = 2.4, 8.2 Hz, 4H), 7.95 (dd, J = 2.4, 8.2 Hz, 4H), 8.31 (d, J = 8.2 Hz, 4H), 8.40 (d, J = 8.2 Hz, 4H), 8.70 (d, J = 2.4 Hz, 4H), 8.84 (d, J = 2.4 Hz, 4H); ¹³C NMR (100 MHz, CD₂Cl₂): δ = 69.8, 71.5, 72.1, 73.1, 74.0, 114.8, 118.2, 118.7, 120.7, 121.3, 121.5, 124.3 (q, ¹J_CF = 271 Hz), 127.0, 128.8, 128.9, 131.2, 131.9 (q, ²J_CF = 33 Hz), 133.5, 134.5, 135.5, 136.5, 137.6, 139.4, 142.4, 146.9, 147.5, 148.0, 151.0, 154.0, 156.7, 159.6 (one signal was missing, possibly because of overlap); HRMS (ESI): calcd for C₂₀₈H₁₈₂F₂₄N₂₀O₂₄, m/z 1899.6621 [M + 2H]²⁺; found: 1899.6617; calcd for C₂₀₈H₁₈₃F₂₄N₂₀O₂₄, m/z 1266.7771 [M + 3H]³⁺; found: 1266.7792; calcd for C₂₀₈H₁₈₄F₂₄N₂₀O₂₄, m/z 950.3347 [M + 4H]⁴⁺; found: 950.3339.