New functional hexahelicenes - Synthesis, chiroptical properties, X-ray crystal structures, and comparative data bank analysis of hexahelicenes

Claudia Wachsmann, Edwin Weber, Mátyás Czugler, Wilhelm Seichter

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Seven new hexahelicenes (3-7, 9, 10) containing different functional group substituents have been synthesized and, in three cases (4, 8, 10), optically resolved. Optical rotations were measured and CD spectra are reported. X-ray crystal structures of the helicenes 1, 3, 4, 8, and 9 have been determined, of which 4 represents a 1:1 clathrate with acetone. These show a concerted interplay of C-H⋯O, C-H⋯π, and π⋯π supramolecular interactions in the packings, mostly yielding stacks of molecules (1, 3, 4, 8). Statistical analysis of the molecular dimensions in these and related crystal structures was carried out in order to identify potential parameters relevant to macroscopic phenomena, including optical rotation.

Original languageEnglish
Pages (from-to)2863-2876
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
Publication statusPublished - Jul 28 2003

Keywords

  • Chiroptical properties
  • Circular dichroism
  • Helicenes
  • Pi interactions
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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