Synthesis of 5,5′-(2,3,5,6-tetramethyl-1,4-phenylene)bis((3,5-dimethyl-4-(2-(4-methoxyphenyl)ethynyl)-2H-pyrrol-2-ylidene)methylene))bis(2,4-dimethyl-3-​(2-​(4-methoxyphenyl)ethynyl)-1H-pyrrole), H2L2

Under a nitrogen atmosphere, a mixture of 5,5′-(2,3,5,6-tetramethyl-1,4-phenylene)bis((3,5-dimethyl-4-iodo-2H-pyrrol-2-ylidene)methylene))bis(2,4-dimethyl-3-iodo-1H-pyrrole) (400.5 mg, 0.387 mmol), Pd(PPh3)2Cl2 (13.8 mg, 0.020 mmol), CuI (3.8 mg, 0.020 mmol), and 1-ethynyl-4-methoxybenzene (338.8 mg, 2.56 mmol) in tetrahydrofuran (10 ml) and triethylamine (4 ml) was heated at 70°C for 4 hours. After evaporation of the solvent, the residue was purified by alumina column chromatography (eluent:hexane/dichloromethane = 2:1, then the ratio of dichloromethane was increased gradually up to 1:2). The red band was collected and evaporated, and the resultant residue was reprecipitated from dichloromethane and methanol to give H2L2 as a red solid (90 mg, 22%). 1H NMR (500 MHz, CDCl3): δ = 7.43 (d, 8H, J = 8.8 Hz), 6.85 (d, 8H, J = 9.1 Hz), 3.82 (s, 12H), 2.50 (s, 12H), 2.15 (s, 12H), 1.60 (s, 12H); 13C NMR (125 MHz, CDCl3): δ = 159.29, 153.50, 140.58, 139.55, 136.15, 133.33, 132.98, 132.75, 132.66, 116.18, 113.97, 95.50, 82.05, 55.32, 17.21, 15.18, 14.50; HR-ESI-TOF-MS [mass/charge ratio (m/z)]: [M + H]+, calculated for C72H67N4O4+, 1051.5162; found, 1051.5095.

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