Syntheses and crystal structures of fused thiophenes: [7]helicene and double helicene, a D2-symmetric dimer of 3,3'-bis(dithieno[2,3-b:3',2'-d]thiophene)

J Org Chem. 2009 Jan 2;74(1):408-11. doi: 10.1021/jo802080g.

Abstract

The efficient synthesis of (TMS)(2)-[7]helicene (rac-3) and double helicene, a D(2)-symmetric dimer of 3,3'-bis(dithieno[2,3-b:3',2'-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular pi-pi interactions and S...S interactions. UV/vis spectra reveal that both 3 and 4 show significant pi-electron delocalization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Dimerization
  • Models, Molecular
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry*
  • Stereoisomerism
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry*

Substances

  • 3,3'-bis(dithieno(2,3-b-3',2'-d)thiophene)
  • Polycyclic Compounds
  • Thiophenes
  • helicenes