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CF = 249.3 Hz).
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0642284290
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note
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The cyclization reaction was conducted in a 100 mL three-neck round-bottom flask equipped with an overhead stirrer, nitrogen inlet, thermometer, Dean-Stark trap and condenser. The flask was charged with 70 mL NMP, 10 mL toluene and 0.35 g of potassium carbonate. The solution was heated to reflux with stirring and allowed to reflux for 1h at 140 °C to dehydrate the system. A solution of the AB monomer (1) (2.5 mmol, 0.791 g) in 65 ml NMP was added over an 8 h period via a syringe pump. After the addition was completed, the reaction was maintained at 170-180 °C for a further 24h. The reaction mixture was subsequently cooled and filtered to remove all the salts. The solvent was distilled off under reduced pressure. The residue redissolved in chloroform and coagulated into methanol. The precipitated product was filtered and dried in a vacuum oven for over 12h at 100 °C. The product was obtained in 90% yield.
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0642376139
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All analyses were performed on the VG Fisons Toffspec MALDI/TOF mass spectrometer equipped with a nitrogen laser (338 nm). The samples were analyzed using a laser energy that was about 76% of maximum power. The linear mode of the instrument was used for all analyses. The accelerating voltage was 23 kV, and the multichannel plate detector was set at 1750 volts. External calibration was performed using bovine insulin (MW 5733.50). The matrix was 0.20 M dithranol in THF, prepared fresh prior to the analysis of each sample. The samples were analyzed as follows: 5 μL of dithranol matrix and 1 μL of sample solution (1.68 μg/μL in THF) were combined and mixed in a centrifugation tube. A 0.5 μL aliquot of this solution was placed on the MALDI/TOF target and dried. The amount of sample on the target was, therefore, approximately 0.01 μg. The spectrum shown was produced by averaging the data produced from 53 laser shots. No AgTFA was used for the analysis of this sample.
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