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拡張されたビス・アントラオックス・キノディメタンは,連続して9回と10回融合した6つ組のリング:中性ディラジカロイドと充電されたディラジカルダイアニオン/ディカーション

Shaoqiang Dong1, Tullimilli Y Gopalakrishna1, Yi Han1

  • 1Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Republic of Singapore.

Journal of the American Chemical Society
|December 13, 2018
PubMed
まとめ

9個 (ABA) と10個 (ANA) の結合リングを持つ二酸化キノジメタンを合成しました ABAは安定し,ANAはダイラジカルな性質を示し,トリフローアセチンの代用製品となる.

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科学分野:

  • 有機合成
  • 材料科学
  • ポリサイクルアロマティック炭化水素

背景:

  • 長く溶けた多循環性芳香炭化水素は,その電子特性のために興味があります.
  • 拡張されたアロマティックシステムにおける構造-特性関係を理解することは極めて重要です.

研究 の 目的:

  • 新しく拡張されたビス・アントラオックス・キノディメタンを合成し,特徴づけること.
  • これらの化合物の電子特性と安定性を調査する.

主な方法:

  • 二酸化キノジメタン (ABAとANA) の化学合成
  • X線結晶分析について
  • 顕微鏡による特徴付け

主要な成果:

  • ABA (9個の結合環) と ANA (10個の結合環) の合成に成功しました.
  • ABAは安定し,軽微なダイラジカル性; ANAは中程度のダイラジカル性を示しています.
  • 三酸塩代用 ANA 製品 (ANA-TFA) の分離
  • レントゲン解析では 脊椎が平らで 五角形だ
  • ディケーションはノナセンとデカセンの同電子である.
  • ABA種は,開いた殻のシングレット・ディラジカロイドの特徴を示している.
  • ANA- TFAディケーションとANAダイアニオンは,分子内クーロン相互作用により,閉殻基底状態を示す.
  • ダイアニオンは,ノナセンとデカセンのテトラニオンの同電子で,折りたたまれた脊椎を持つ.

結論:

  • 拡張されたビス・アントラオキノジメタンは合成され,特徴づけられる.
  • ダイラジカル特性と安定性は,融合したリングの数と分子内相互作用によって影響されます.
  • これらの化合物は,大型多循環芳香炭化水素の電子構造を理解するためのモデルとして機能します.