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Chemical Communications

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Hot Article: Pi-bowls


31 May 2007

A potential new route to organic electronic materials has been developed by scientists in Japan.

Toshikazu Hirao and colleagues from Osaka University have created extended bowl, -shaped pi-conjugated molecules based on sumanene, a symmetrical partial structure of Buckminster fullerene, C60.

The team were able to achieve pi-extension at the benzyl positions of sumanene using a condensation reaction under mild basic conditions. They successfully attached seven different derivatives with extended pi-conjugation. Subsequent spectroscopic characterisation revealed that the thiophene derivatives showed a remarkable red-shift absorption and a narrow band gap indicating its potential use in organic electronic materials. 

                Schematic diagram of reaction

When asked to comment on their work Hirao said, 'Our motive depends on the establishment of another class of pi-conjugated systems. The buckybowl will provide a third key material in addition to fullerenes and carbon nanotubes.'

The group foresee that molecular electronic materials including organic semiconductors will be one of the most important uses of their new material in the future.   

Jenna Wilson

Link to journal article

Synthesis and characterization of -extended bowl-shaped -conjugated molecules
Toru Amaya, Koichi Mori, Hsyueh-Liang Wu, Satoshi Ishida, Jun-ichi Nakamura, Kazuhiko Murata and Toshikazu Hirao, Chem. Commun., 2007, 1902
DOI: 10.1039/b701322a