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Making a ring of eight benzenes

By Tetsuo Satoh |

Professor Shigeru Yamago and colleagues at the Institute for Chemical Research, Kyoto University (Japan; www.scl.kyoto-u.ac.jp/~yasuyuki/) have synthesized [8]cycloparaphenylene for the first time. The 11-nm-dia. molecule consists of eight benzene molecules linked together in a closed chain. The compound has a strong absorption peak at 340 nm and fluoresces yellow-green light at around 540 nm — properties that may find applications in organic light-emitting diodes (OLEDs), organic conductors and battery electrodes. Previously, other research groups have synthesized ring compounds with 9 or 12 benzenes linked together. The compound is synthesized under mild conditions in a three-step process whereby 4,4’-bis(trimethylstannyl)biphenyl and [PtCl2(cod)] (cod=1,5-cyclooctadiene) first react to form a square-shaped platinum-biphenyl intermediate. The planar complex is then separated, and heated with bromine at 95°C. A 25% yield of [8]cycloparaphenylene is achieved. The researchers plan to apply the technique for synthesizing cylinder-shaped materials, such as carbon nanotubes (CNTs). Yamago believes their procedure will enable the control of the thickness, length and twisting degrees of CNTs.   Click here for a full…
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