تفاعل #85589

معادلة التفاعل

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

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

4,4′-didodecyltolane

→

monomer 6b

1,2-Bis(4-chlorophenyl)-3,6-bis(biphenyl-3-yl)-4,5-bis(4-dodecylphenyl)benzene

المذيبات

hexane

diphenyl ether

propylene carbonate

ظروف التفاعل

المعالجة

1. 1
   أخرىfor 2×12 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 1.84 g of 2,5-di([1,1′-biphenyl]-3-yl)-3,4-bis(4-chlorophenyl)cyclopenta-2,4-dienone (8b, 3.03 mmol) and 1.72 g of 4,4′-didodecyltolane (3.34 mmol) in 12 ml of diphenyl ether and 5 ml of propylene carbonate was heated to 230° C. in a microwave reactor at power 300 watts and a maximum pressure of 7 bar for 2×12 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, 1.85 g of monomer 6b were obtained as a colorless oil (56%, 1.69 mmol). Elemental analysis measured: C 85.6; H 7.9% (calculated for C78H84Cl2: C, 85.8; H, 7.8%); 1H NMR (700 MHz, d8-THF) δ=7.27 (dt, J=7.7, 4.0 Hz, 4H, CH), 7.22-7.16 (m, 6H, CH), 7.10 (d, J=10.0 Hz, 4H, CH), 6.94 (t, J=7.7 Hz, 4H, CH), 6.91 (s, 2 Hv), 6.88 (d, J=8.4 Hz, 2H, CH), 6.87-6.81 (m, 2H, CH), 6.81-6.77 (m, 2H, CH), 6.77-6.70 (br m, 6H, CH), 6.66 (d, J=7.5 Hz, 2H, CH), 2.41-2.28 (m, 4H, α-CH2), 1.44-1.34 (m, 4H, β-CH2), 1.34-1.03 (m, 36H, —CH2—), 0.89 (t, J=6.9 Hz, 6H, —CH3); 13C NMR (175 MHz, d8-THF) δ=142.44, 142.42, 142.27, 141.88, 141.74, 140.76, 140.74, 140.68, 140.59, 140.56, 140.14, 140.10, 139.09, 139.05, 134.18, 134.14, 134.06, 134.01, 132.56, 132.50, 132.47, 132.30, 132.26, 131.69, 131.41, 129.37, 128.20, 128.07, 127.90, 127.88, 127.84, 127.81, 127.80, 127.74, 125.14, 125.12, 36.36, 36.33, 33.06, 32.37, 32.34, 30.85, 30.81, 30.77, 30.75, 30.61, 30.60, 30.51, 30.00, 29.98, 25.94, 25.82, 23.74, 14.62; MS (MALDI-TOF): m/z (%): 1091.0 (100) [M+] (calculated for C78H84Cl2: 1090.6); Rf (hexane with 6% ethyl acetate)=0.65.

المصدر