Synthesis, π-face-selective aggregation, and π-face chiral recognition of configurationally stable c3-symmetric propeller-chiral molecules with a π-core

Nozomi Saito, Ryo Terakawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

The C3-symmetric propeller-chiral compounds (P,P,P)-1 and (M,M,M)-1 with planar π-cores perpendicular to the C3-axis were synthesized in optically pure states. (P,P,P)-1 possesses two distinguishable propeller-chiral π-faces with rims of different heights named the (P/L)-face and (P/H)-face. Each face is configurationally stable because of the rigid structure of the helicenes contained in the π-core. (P,P,P)-1 formed dimeric aggregates in organic solutions as indicated by the results of 1HNMR, CD, and UV/Vis spectroscopy and vapor pressure osmometry analyses. The (P/L)/(P/L) interactions were observed in the solid state by single-crystal X-ray analysis, and they were also predominant over the (P/H)/(P/H) and (P/L)/(P/H) interactions in solution, as indicated by the results of 1H and 2D NMR spectroscopy analyses. The dimerization constant was obtained for a racemic mixture, which showed that the heterochiral (P,P,P)-1/(M,M,M)-1 interactions were much weaker than the homochiral (P,P,P)-1/(P,P,P)-1 interactions. The results indicated that the propeller-chiral (P/L)-face interacts with the (P/L)-face more strongly than with the (P/H)-face, (M/L)-face, and (M/H)-face. The study showed the π-face-selective aggregation and π-face chiral recognition of the configurationally stable propeller-chiral molecules. Propeller chirality: C 3-symmetric propeller-shaped compounds containing π-cores were synthesized in optically pure states, which possess two distinguishable configurationally stable propeller-chiral π-faces (see figure). π-Face-selective aggregation and π-face chiral recognition were observed in the solid state and in solution.

Original languageEnglish
Pages (from-to)5601-5607
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number19
DOIs
Publication statusPublished - 2014 May 5

Keywords

  • aggregation
  • annulenes
  • helicene
  • recognition
  • selectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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