Compound 5
[2][(N-(3,5-Diethylester-benzyl)-3,5-diethylester-aniline)-rotaxa-([24]crown-6)]
From: Metal–organic frameworks with dynamic interlocked components
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InChIKey SEFWRJGLHRVGJW-UHFFFAOYSA-N
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
4 (100 mg 0.11 mmol) was dissolved in CHCl3 (10 mL) and 2.0 equivalence of triethylamine (22 mg) was added and stirred for 1 h. The solvent was subsequently removed via a rotary evaporator and placed under high vacuum to remove any residual triethylamine. A two layer extraction was performed using EtOAc and H2O. The aqueous phase was discarded and the organic layer was washed with H2O (2 x 10 mL), dried over MgSO4, and the solvent removed to yield a white solid; yield (84 mg 94%), Mp 92-96 oC. 1H NMR (500 MHz, CD2Cl2): δ = 8.63 (d, 2H, Ar-H,3J=1.5 Hz), 8.54 (s, 1H, Ar- H), 7.85 (s, 1H, Ar- H), 7.69 (d, 2H, Ar- H, 3J=1.0 Hz), 5.85 (t, 1H, N-H, 3J=5.0 Hz), 4.74 (d, 2H, Ar-CH2, 3J=5.0 Hz), 4.39 (q, 4H, OCH2CH3, 3J=7.0 Hz), 4.35 (q, 4H, OCH2CH3, 3J=7.0 Hz), 3.6-3.2 (m, 24H, OCH2CH2OCH2CH2), 1.46 (m, 12H, OCH2CH3, 3J=7.5 Hz), 1.26-1.0 (m, 12H, OCH2CH2CH2CH2), 13C NMR (125 MHz, CD2Cl2): δ = 167.3, 166.7, 150.7, 142.3, 135.9, 131.6, 131.0, 129.28, 118.6, 117.6, 72.2, 71.7, 71.5, 71.4, 71.3, 71.2, 61.6, 61.3, 47.3, 30.6, 29.5, 26.2, 14.8. HR-MS (ESI-TOF): Calculated for [M + H]+ [C43H66NO14]+m/z = 820.4477; found m/z = 820.4445.
