Toluene → 5,10-Bis(2-octyldodecyloxy)naphtho[2,3-b:6,7-b']dithiophene

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Reaction Steps

Compound (3) (0.400 g, 1.33 mmol) was weighed into a flame-dried 2-neck flask fitted with a condenser. Toluene (13 mL), 2-octyl-1-dodecanol (1.59 g, 5.32 mmol), and p-toluenesulfonic acid (0.051 g, 0.266 mmol) were then added. The mixture was placed in a 130° C. heat bath and stirred overnight. The mixture was diluted with water, extracted with dichloromethane, dried over MgSO4, filtered and concentrated. The product was purified via column chromatography (10% dichloromethane in hexanes) to yield compound (4a) as a yellow solid (0.735 g, 66%). 1H NMR (500 MHz, CDCl3, 298 K): 8.46 (s, 2H); 7.45 (m, 4H); 4.27 (d, J=5.4 Hz, 4H); 2.01 (quintet, J=6.2 Hz, 2H); 1.73 (m, 4H); 1.47 (m, 60H); 0.89 (m, 12H) ppm. 13C NMR (125 MHz, CDCl3, 298 K): 149.87; 139.70; 127.98; 127.08; 124.83; 124.62; 110.84; 75.85; 39.38; 31.96; 31.42; 30.18; 29.76; 29.71; 29.43; 29.41; 27.06; 22.74; 14.18 ppm. HRMS (ESI-TOF-MS): m/z calcd for C54H88O2S2 832.6220, found 832.6217.

Provenance & Evidence