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A nano cage made from a stack of benzenes

By Tetsuo Satoh |

Professor Kenichoro Itami and his group at Nagoya University (synth.chem. nagoya-u.ac.jp) have synthesized a cage-type carbon nano-molecule, Carbon Nano-cage, composed of 20 condensed benzene rings — C120H78. The group used a procedure it developed four years ago to synthesize carbon nano-rings with the ability to eliminate the distortion of ring-type benzene structures during synthesis steps. First, they synthesized an unstrained cyclic precursor by assembling six L-shaped units [ cis -di(p-bromophenyl)cyclohexane derivative] and two three-way units (1,3,5-triborylbenzene) by cross- and homo-coupling reactions. Then, they obtained carbon nano-cages through acid-mediated aromatization of the cyclohexane moieties in the precursor. The nano-cage is a white solid that is soluble in almost all organic solvents and stable at temperatures up to 300°C. It has a 1.8-nm inner diameter, which could confine a guest molecule. In collaboration with the National Institute of Advanced Industrial Science and Technology, the researchers found that the carbon nano-cage has a large two-photon absorption cross section and a high fluorescence quantum yield of 87%. These properties are advantageous for such applications as organic electroluminescent…
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