تفاعل #85587

معادلة التفاعل

2,5-di([1,1′-biphenyl]-3-yl)-3,4-bis(4-bromophenyl)cyclopenta-2,4-dienone

2,5-Di([1,1′-biphenyl]-3-yl)-3,4-bis(4-bromophenyl)cyclopenta-2,4-dienone

4,4′-dibromotolane

→

monomer 6a

1,2-Bis(4-bromophenyl)-3,6-bis(biphenyl-3-yl)-4,5-diphenylbenzene

المذيبات

hexane

diphenyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىfor 3×12 h
2. 2
   أخرىpurified by column chromatography (silica, hexane with 6% ethyl acetate)
3. 3
   أخرىAfter purification by means of recycling GPC
4. 4
   أخرىdrying under high vacuum

الإجراء التجريبي

A degassed solution of 300 mg of 2,5-di([1,1′-biphenyl]-3-yl)-3,4-bis(4-bromophenyl)cyclopenta-2,4-dienone (8a, 0.432 mmol) and 77.0 mg of 4,4′-dibromotolane (0.432 mmol) in 3 ml of diphenyl ether was heated to 230° C. in a microwave reactor at power 300 watts and a maximum pressure of 7 bar for 3×12 h. After cooling to room temperature, the reaction solution was diluted with hexane and purified by column chromatography (silica, hexane with 6% ethyl acetate). After purification by means of recycling GPC and drying under high vacuum, 145 mg of monomer 6a were obtained in the form of colorless crystals (40%, 0.172 mmol). Elemental analysis measured: C 76.7; H 3.1% (calculated for C54H36Br2: C, 76.8; H, 4.3%); 1H NMR (700 MHz, d8-THF) δ=7.30-7.25 (m, 4H, CH), 7.23-7.17 (m, 6H, CH), 7.13 (d, J=1.5 Hz, 1H, CH), 7.12-7.11 (m, 1H, CH), 7.11-7.09 (m, 4H, CH), 7.09-7.06 (m, 2H, CH), 6.95 (s, 1H, CH), 6.94 (br s, 2H, CH), 6.93 (s, 1H, CH), 6.91 (t, J=4.1 Hz, 2H, CH), 6.89 (d, J=8.0 Hz, 2H, CH), 6.85 (d, J=7.0 Hz, 4H, CH), 6.83 (d, J=2.0 Hz, 2H, CH), 6.81 (d, J=1.4 Hz, 1H, CH), 6.79 (d, J=8.3 Hz, 2H, CH), 6.78 (s, 1H, CH); 13C NMR (125 MHz, d2-TCE) δ=141.05, 140.74, 140.20, 140.00, 139.44, 139.03, 138.52, 133.03, 132.92, 131.30, 131.15, 130.26, 129.92, 129.85, 128.42, 127.17, 126.87, 126.62, 126.52, 125.20, 124.15, 120.18, 119.51; MS (MALDI-TOF): m/z (%): 845.1 (100) [M+] (calculated for C54H36Br2: 844.1); Rf (hexane with 6% ethyl acetate)=0.40; m.p. (° C.): decomposition at >400° C.

المصدر