Blog

Adamantane-annulated arenes

Adamantane Annulation to Arenes: A Strategy for Property Modulation of Aromatic π-Systems

Takaku Yoshihara, Hiroki Shudo, Akiko Yagi*, Kenichiro Itami*
J. Am. Chem. Soc.2023, ASAP. DOI: 10.1021/jacs.3c02788

 

Peripheral structural modifications of arenes are widely used to control or improve the optoelectronic properties, molecular assembly, and stability of aromatic π-materials as well as to explore new functions. However, known modifications are often tedious and complex; therefore, a simple yet powerful modification strategy is needed. We discovered that annulation with a simple adamantane scaffold exerts a significant impact on the properties, alignment, and stability of aromatic π-systems. This unprecedented adamantane annulation was achieved by a two-step transformation of metallated arenes and 4-protoadamantanone, generating a range of adamantane-annulated arenes. Analysis of structural and electronic properties uncovered unique effects of the process, such as high solubility and enhanced conjugation. The oxidation of adamantane-annulated perylenes produced strikingly stable cationic species with emission extended to the near-infrared region. This simple property modulation of aromatic π-systems would not only create potentially ground-breaking π-materials but also novel nanocarbon materials, such as diamond–graphene hybrids.

Related post

  1. Structurally uniform and atomica…
  2. One-Step Annulative π-Extension …
  3. Making Dimethylamino a Transform…
  4. Palladium-Catalyzed Carbon-Carbo…
  5. Branch-Selective Allylic C–H Car…
  6. Late-Stage C–H Coupling Enables …
  7. Direct C-H Arylation of Polycycl…
  8. Phenanthro[9,10-a]corannulene by…

最近の記事

Flickr@Itamilab

天池先輩からコーヒースープ伴夫妻からのお歳暮です!潤さん、宮村さん、ありがとうございます!!武藤さん、ビールありがとうございます!平賀大都わーいやなさん、あつしさん、ありがとうございます!!だいぶ前だけど、Stripes look #ootdHalloween lookラインを洗う時ですら格好良く。戸谷先生教育実習!imageけいしゅう、誕生日おめでとう!誕生日は英吉家!!3年生に名古屋ぼろ勝ちアピール中!!アリシア卒業おめでとう女子会!
PAGE TOP