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- Title
Synthesis of Twisted [n]Cycloparaphenylene by Alkene Insertion.
- Authors
Terabayashi, Tomoaki; Kayahara, Eiichi; Zhang, Yichen; Mizuhata, Yoshiyuki; Tokitoh, Norihiro; Nishinaga, Tohru; Kato, Tatsuhisa; Yamago, Shigeru
- Abstract
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‐insertved [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 through 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 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 solution. Despite a twist, 1 has in‐plane conjugation and possesses a unique size dependence of the electronic properties: namely, the opposite size dependency of the HOMO–LUMO energy relative to conventional π‐conjugated molecules.
- Subjects
ALKENES; X-ray diffraction; LOW temperatures; TOPOLOGY
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 2, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202214960