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A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene Synthesized from Pillar[6]arene.
A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene Synthesized from Pillar[6]arene.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2020 Jul 22; Vol. 142 (29), pp. 12850-12856. Date of Electronic Publication: 2020 Jul 09. - Publication Year :
- 2020
-
Abstract
- The synthesis, structure, and properties of methylene-bridged [6]cycloparaphenylene ([6]CPP), a nonalternant aromatic belt, are described. This belt-shaped methylene-bridged [6]CPP, in which each phenylene unit is tethered to its neighbors by methylene bridges, was constructed through 6-fold intramolecular nickel-mediated aryl-aryl coupling of triflate-functionalized pillar[6]arene in 18% isolated yield. As compared to the analogous [6]CPP, the methylene bridges coplanarize neighboring paraphenylene units and enhance the degree of π-conjugation, which results in a significant decrease in energy gap. Moreover, the incorporation of small molecules in the defined pocket of methylene-bridged [6]CPP makes it an attractive supramolecular architecture. Methylene-bridged [6]CPP is characterized by high internal strain energy reaching 110.2 kcal mol <superscript>-1</superscript> , attributed to its restricted structure. This work not only exhibits an efficient strategy to construct a new family of aromatic belt, but also showcases their properties, which combine the merits of CPPs and pillararenes.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 142
- Issue :
- 29
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 32603101
- Full Text :
- https://doi.org/10.1021/jacs.0c06007