Compound 8
9-[4-(4-{2-[2,5-Bis(octyloxy)-4-[2-(4-{pentakis[4-(2-{4-[2-(4-{4-[2,7-bis({2-[4-ethynyl-2,5-bis(octyloxy)phenyl]ethynyl})-9H-carbazol-9-yl]phenyl}phenyl)ethynyl]-2,5-bis(octyloxy)phenyl}ethynyl)phenyl]phenyl}phenyl)ethynyl]phenyl]ethynyl}phenyl)phenyl]-2,7-bis({2-[4-ethynyl-2,5-bis(octyloxy)phenyl]ethynyl})-9H-carbazole
From: Fluctuating exciton localization in giant π-conjugated spoked-wheel macrocycles
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InChIKey UGPTXLNBXCUFFQ-UHFFFAOYSA-N
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a solution of 7 (270 mg, 23.5 µmol) in THF (23 mL) a solution of TBAF in THF (1 M) (0.707 mmol, 0.71 mL) was added at 0 °C. The reaction was stirred 20 min at 0 °C and 3 h at r.t. Then, extraction with MTBE and dichloromethane was followed by washing with water and brine. After drying over MgSO4 and removal of the solvent, the crude product was obtained and purified by column chromatography (CH:DCM = 60:40 – 52:48) and recGPC. 8 (166 mg, 17.9 µmol, 74 %) was isolated as a yellow solid. 1H NMR (500 MHz, CDCl3, 298 K) δ [ppm] = 8.09 (d, 3JH,H = 8.1 Hz, 12 H), 7.87 (d, 3JH,H = 8.3 Hz, 12 H), 7.76 – 7.59 (m, 48 H), 7.49 (d, 3JH,H = 8.4 Hz, 12 H), 7.16 (d, 3JH,H = 7.9 Hz, 12 H), 7.03 (s, 6 H), 7.02 (s, 6 H), 6.99 (s, 12 H), 6.97 (s, 12 H), 6.86 (d, 3JH,H = 8.0 Hz, 12 H), 4.14 – 3.93 (m, 72 H), 3.33 (s, 12 H), 1.99 – 1.73 (m, 72 H), 1.65 – 1.14 (m, 360 H), 1.03 – 0.75 (m, 108 H); 13C NMR (126 MHz, CDCl3, 298 K) δ [ppm] = 154.30, 153.77, 153.65, 153.57, 141.30, 140.19, 140.16, 140.12, 139.81, 136.49, 132.34, 131.44, 130.60, 128.65, 127.69, 127.07, 124.27, 123.28, 123.20, 121.22, 120.97, 120.57, 117.95, 117.11, 116.99, 116.84, 114.82, 114.35, 113.78, 113.22, 112.61, 96.19, 95.25, 94.62, 87.32, 86.37, 86.10, 82.46, 80.14, 69.76, 69.72, 31.96, 31.95, 31.92, 31.89, 29.53, 29.50, 29.46, 29.44, 29.42, 29.39, 29.38, 29.34, 29.27, 26.24, 26.13, 26.09, 26.03, 22.85, 22.84, 22.78, 14.34, 14.27, 14.24, 14.20. MS (MALDI-TOF, DCTB) (calcd. for C654H768N6O36 monoisotopic: 9281.84, distr. max.: 9289.11): m/z 9788.3 [M+2*DCTB]+, 9539.0 [M+DCTB]+, 9289.1 [M]+, 9170.0 [M-C8H17]+; GPC (in THF vs. PS): Mp = 11360 g mol-1.
