F 3,4-BHOT A three-necked round bottom flask was outfitted with Soxhlet
F three,4-BHOT A three-necked round bottom flask was outfitted with Soxhlet extractor charged with activated 4 molecular sieves, high efficiency condenser, and magnetic stir bar. Toluene (100 mL) and p-toluenesulfonic acid (0.40 g, 2.1 mmol) had been added towards the flask, and stirring was initiated. The flask was sealed using a rubber GSK2646264 custom synthesis septum and heated at 60 C under argon. The mixture was stirred for 50 min at that temperature, and n-hexanol (5.78 mL, 46.0 mmol) was added by means of the septum by way of syringe. Right after an added 5 min, 3,4dimethoxythiophene (three.00 g, 26.three mmol) in toluene (5 mL) was added gradually through the septum via syringe. The mixture was heated for 36 h at 130 C below argon. The mixture was cooled to area temperature and transferred to a 500 mL separatory funnel. The crude reaction mixture was washed 3 occasions with deionized water (60 mL every single), as soon as with sat. NaHCO3 (60 mL), and after again with water (60 mL). The organic fraction was collected, dried more than anhydrous MgSO4 , and filtered. The filtrate was evaporated under decreased pressure to offer the crude item as a brown oil. The crude solution was purified by short-path Methyl jasmonate web vacuum distillation. Yield four.51 g (69 ) solution as a light-yellow oil. 1 H NMR (Figure S2, 400 MHz, CDCl3 ) : six.16 (s, 2H), three.98 (t, 4H), 1.81 (p, 4H), 1.44 (m, 4H), 1.33 (m, 8H), 0.90 (t, 6H); Lit. [49]: 6.15 (s, 2H), 3.98 (t, 4H), 1.81 (m, 4H), 1.35.43 (m, 12H), 0.97 (t, 6H). two.three. Polymerizations two.three.1. Common Procedure–Reverse Addition Oxidative Polymerization A common reverse addition polymerization process was carried out as follows: anhydrous FeCl3 (two.three or 4 molar equivalents relative to monomer) was weighed and rapidly transferred to a Schlenk flask. The flask was purged with argon, and dry chlorobenzene (25 mL) was added. The oxidant suspension was stirred rapidly for three min below argon. Monomer (0.7.six mmol) was dissolved in dry chlorobenzene (five mL) and added dropwise towards the stirred oxidant suspension by way of syringe (BD, Franklin Lakes, NJ, USA). The mixture was stirred for 24 h at space temperature, soon after which the polymer was precipitated by dropwise addition of your reaction mixture into an excess (250 mL) of quickly stirred methanol. The polymer was collected by vacuum filtration and washed thoroughly with methanol. The polymer was permitted to air dry just before becoming resuspended in chlorobenzeneMaterials 2021, 14, x FOR PEER Assessment Components 2021, 14, x FOR PEER Assessment Materials 2021, 14, 6146 Materials 2021, 14, x FOR PEER REVIEW7 of 15 7 of 15 7 of 15 7 ofsynthesized by FeCl3-initiated oxidative polymerization beneath weight-average degree values had been determined in the Table three. Weight-average molecular weight (M elugram. elution volume in the most intense peak with the GPCw) in g/mol anddifferent situations. Mwof polymerization (Xw) for polymers elution volume ofFeCl3-initiated oxidative polymerization below diverse circumstances. Mw values had been determined in the synthesized by the most intense peak from the GPC elugram. Table three. Weight-average molecular weight (Mw) in g/mol and weight-average degree of polymerization (Xw) for polymers Order elugram. Equivalents Reaction Yield Mw elution volume from the most intense peak with the GPCof oxidative Order of Entry synthesized by FeCl3-initiatedAcronym polymerization under diverse situations. Mw values had been determined from w Structure X the M Reaction Addition Equivalents FeCl3 Time (g/mol) w Yield Xw Entry Structure elution volume on the mostAcronym in the GPC of i.