期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 29, 页码 12850-12856出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c06007
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资金
- ERATO program from JST [JPMJER1302]
- JSPS KAKENHI [19H05463, JP19H02701, JP19K22183, 19K15537]
- CREST program from JST [JPMJCR19R1]
- JSPS Postdoctoral Fellowships for Research in Japan
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [19K15537] Funding Source: KAKEN
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 pi-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(-1), 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.
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