Synthesis and characterisation of novel rod–disc oligomers

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• Synthesis of 4a: in a typical reaction, 2 (100 mg, 0.32 mmol), 4′‐[(6‐bromohexyl)oxy]‐1,1′‐biphenyl‐4‐carbonitrile (1.4 g, 3.9 mol), Cs2CO3 (1.3 g, 3.9 mol) were mixed in a small glass vial and loosely covered with a rubber septum. The mixture was heated in an unmodified household microwave oven at 360 W for 10 min (30 s×20). The vial was taken out and water (10 ml) was added. Then the mixture was extracted with dichloromethane (3×10 ml). The combined organic extracts were washed with distilled water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was then passed through a small column chromatography using 1:1 dichloromethane/petroleum ether as an eluent to afford 4a (300×mg, 46%)
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• Selected data for compound 4a: 1H NMR (400 MHz, CDCl3): 7.69 (d, J = 8.2 Hz, 12H), 7.65 (d, J = 8.2 Hz, 12H), 7.59(s, 2H), 7.45 (d, J = 8.6 Hz, 12H), 6.95 (d, J = 8.6 Hz, 12H), 3.95–4.25 (m, 24H), 1.4–2.1 (m, 48H). IR (KBr, all the derivatives 4a–4c showed similar spectra, νmax/cm−1): 2939, 2221, 1660, 1602, 1568, 1494, 1315, 1290, 1178, 1128,997, 821. UV–visible (CHCl3, all the derivatives 4a–4c showed similar spectra): λmax 300 nm. Elemental analysis: calculated for C128H122N6O14, C 78.10, H 6.25, N 4.24%; found, C 77.99, H 6.01, N 4.15%
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