Tri-o-tolylphosphine → Benzo(B)Thiophene

Participants

Reaction Conditions

Reaction Steps

2,6-bis(Trimethylstannyl)-benzo[1,2-b:4,5-b′]dithiophene-4,8-(5-(2-hexyldecyl)-2-thiophenecarboxylic acid) ester (101.0 mg (81.0%), 0.672 mmol), 4,7-bis(5-bromo-2-thienyl)-5-chloro-2,1,3-benzothiadiazole (16.56 mg, 0.0336 mmol), 4,7-bis(5-bromo-4-dodecyl-2-thienyl)-5-chloro-2,1,3-benzothiadiazole (27.87 mg, 0.0336 mmol), Pa2dba3 (2.46 mg, 0.0027 mmol), P(o-tol)3 (3.27 mg, 0.0108 mmol) were placed in a 100 mL schlenk flask. The flask was degassed and backfilled with argon three times. Dry chlorobenzene (11 mL) was injected and the reaction was heated in a 135° C. heat bath for 18 hr. The reaction was cooled to room temperature and the contents of the flask were poured into methanol (100 mL). The precipitates were collected by filtration. The solid was subjected to Soxhlet extraction and washed with methanol (4 h), then ethyl acetate (16 h). The final product was extracted out with dichloromethane and weighed 35.0 mg after drying under vacuum (37.0%). Elemental Analysis: Calcd. C, 67.51; H, 7.46; N, 1.99. Found: C, 67.73, H, 7.23, N, 1.67. FIG. 2 shows the UV-vis spectra of the polymer in thin film form and as a solution in chloroform.

Provenance & Evidence