Synthetic study for carbon nanotube skeleton using bowl-shaped molecule sumanene

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To synthesize never-achieved carbon nanotube skeletons using synthetic organic chemistry method, I investigated a new synthetic strategy based on the bowl-shaped π-conjugated molecule, sumanene. Consequently, it was revealed that the Pd-catalyzed cross-coupling reaction to introduce the benzaldehyde moiety at the aromatic position of sumanene, followed by the benzyl anion generation, 1,2-addition, and dehydrative aromatization gave the expanded fused-benzene rings to sumanene. Thus-synthesized π-conjugated molecules correspond to a partial structure of carbon nanotube skeleton.