Ammonia-driven chirality inversion and enhancement in enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by diguanidino-γ-cyclodextrin

Jiabin Yao, Zhiqiang Yan, Jiecheng Ji, Wanhua Wu, Cheng Yang, Masaki Nishijima, Gaku Fukuhara, Tadashi Mori, Yoshihisa Inoue

研究成果: Article査読

64 被引用数 (Scopus)

抄録

In the supramolecular photocyclodimerization of 2-anthracenecarboxylate mediated by 6A,6D-diguanidino-γ-cyclodextrin (CD), the chiral sense and enantiomeric excess of the photoproduct were dynamic functions of temperature and cosolvent to afford the (M)-anti head-to-head cyclodimer in 64% ee in aqueous methanol at-70 °C but the antipodal (P)-isomer in 86% ee in aqueous ammonia at-85 °C, while the corresponding diamino-γ-CD host did not show such unusual photochirogenic behaviors. The ee landscape was very steep against the temperature and sign-inverted against the ammonia content to reveal the opposite temperature dependence at low and high ammonia contents, for which an altered solvent structure and/or guanidinium-carboxylate interaction mode would be responsible.

本文言語English
ページ(範囲)6916-6919
ページ数4
ジャーナルJournal of the American Chemical Society
136
19
DOI
出版ステータスPublished - 2014 5月 14
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

フィンガープリント

「Ammonia-driven chirality inversion and enhancement in enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by diguanidino-γ-cyclodextrin」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル