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

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6916-6919
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number19
DOIs
Publication statusPublished - 2014 May 14
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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