Compound 5
4-(((4-((9-(4'-((4-Ethynyl-2,5-bis(octyloxy)phenyl)ethynyl)-[1,1'-biphenyl]-4-yl)-7-((4-(((3-isocyanopropyl)diisopropylsilyl)ethynyl)-2,5-bis(octyloxy)phenyl)ethynyl)-9H-carbazol-2-yl)ethynyl)-2,5-bis(octyloxy)phenyl)ethynyl)diisopropylsilyl)butanenitrile
From: Fluctuating exciton localization in giant π-conjugated spoked-wheel macrocycles
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InChIKey VRJYNIYASYFWEA-UHFFFAOYSA-N
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
4 (1.068 g, 548 µmol) and K2CO3 (379 mg, 2.740 mmol) were suspended in THF (50 mL) and methanol (20 mL) and stirred for 1 h at r.t. before the reaction was diluted with MTBE. The organic phase was washed with aq. H2SO4 (10 %, until acidic), water, and brine. After drying over anhydrous MgSO4 and removal of the solvent under reduced pressure, the residue was purified by column chromatography (CH:DCM = 2:1 – 11:9). 5 (945 mg, 518 µmol, 95 %) was obtained a yellow oil that solidified upon standing. 1H NMR (400 MHz, CDCl3, 298 K) δ [ppm] = 8.10 (d, 3JH,H = 8.1 Hz, 2 H), 7.87 (d, 3JH,H = 8.5 Hz, 2 H), 7.76 – 7.61 (m, 8 H), 7.55 – 7.46 (m, 2 H), 7.04 (s, 1 H), 7.01 (s, 1 H), 6.97 (s, 2 H), 6.94 (s, 2 H), 4.11 – 3.99 (m, 8 H), 3.96 (t, 3JH,H = 6.4 Hz, 4 H), 3.37 (s, 1 H), 2.43 (t, 3JH,H = 7.0 Hz, 4 H), 1.97 – 1.72 (m, 16 H), 1.66 – 1.44 (m, 12 H), 1.44 – 1.17 (m, 48 H), 1.17 – 1.00 (m, 28 H), 0.97 – 0.78 (m, 22 H); 13C NMR (101 MHz, CDCl3, 298 K) δ [ppm] = 154.50, 154.31, 153.64, 153.51, 141.31, 140.07, 139.91, 136.53, 132.36, 128.64, 127.70, 127.07, 124.26, 123.27, 123.06, 121.26, 120.56, 119.89, 117.94, 117.79, 117.03, 116.25, 114.70, 113.32, 113.19, 112.86, 104.04, 96.21, 95.26, 94.75, 87.01, 86.33, 82.51, 80.14, 69.89, 69.80, 69.78, 69.28, 31.98, 31.95, 31.94, 31.89, 29.53, 29.51, 29.47, 29.44, 29.42, 29.41, 29.38, 29.37, 29.30, 26.23, 26.21, 26.11, 26.06, 22.82, 22.79, 22.78, 21.42, 20.88, 18.36, 18.12, 14.24, 14.22, 14.20, 11.93, 9.75; MS (MALDI-TOF, DCTB) (calcd. for C122H163N3O6Si2 monoisotopic: 1822.21, distr. max.: 1823.79): m/z 2072.2 [M+DCTB]+, 1822.0 [M]+; GPC (in THF vs. PS): Mp = 2540 g mol‑1.
