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Synthesis of Twisted [N]Cycloparaphenylene by Alkene Insertion

Mono-alkene-inserted [N]cycloparaphenylenes 1 [(ene)-[N]CPP] with N = 6, 8, and 10, mono-ortho-phenylene-inserted [6]CPP 2, and di-alkene-inserted [N]CPP 3 [(ene)2-[N]CPP] with N = 4, 6, and 8 were synthesized by fusing CPP precursors and alkene or ortho- phenylene groups via coupling reactions. Single-crystal X-ray diffraction analyses reveal that the strips formed by the π-surfaces of 1 and 2 exhibited a Möbius topology in the solid state. While the Möbius topology in the parent 1 and 2 in a solution was lost due to the free rotation of the paraphenylene unit even at low temperatures, ene-[6]CPP 4 with eight 1-pyrrolyl groups preserved the Möbius topology even in a solution. Despite a twist, 1 has in-plane conjugation and possesses a unique size dependence of the electronic properties; i.e., the opposite size dependency of the HOMO-LUMO energy relative to conventional π-conjugated molecules.

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