7:8,9:10-dibenzo-1,2,3,4-tetrafluoro- triphenylene: synthesis, structure, and photophysical properties of a novel [5]helicene

J Org Chem. 2005 Jun 24;70(13):5309-12. doi: 10.1021/jo0506231.

Abstract

A simple and efficient synthesis and crystallographic analysis of the partially fluorinated 7:8,9:10-dibenzo-1,2,3,4-tetrafluorotriphenylene, 1, in 59% yield is reported. Compound 1 is a blue luminescent [5]helicene in both solution and the solid state. It spontaneously forms enantiomorphous single crystals from racemic samples and exhibits slipped, face-to-face F...C(pi) contacts within the stacks of molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Polycyclic Compounds / analysis
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry

Substances

  • Fluorescent Dyes
  • Polycyclic Compounds
  • helicenes