Projekty

Current Activities

The group of Chemistry of Functional Molecules is focused on the preparation and use of helicenes and their congeners. Recently, an original approach to helicene frameworks has been developed that is based on [2+2+2] cycloisomerization of aromatic triynes under transition metal catalysis. This approach represents a new paradigm for the non-photochemical preparation of helicenes and their substituted derivatives in an easy, convergent, and modular way. The methodology has matured to serve as a reliable and general synthetic tool providing tailor-made helically chiral targets.



scheme 1

An example of the helicene synthesis:

scheme 2

Selected compounds prepared recently:

scheme 3

Diastereoselective synthesis of helicene-like compounds:

scheme 4


 

Visions

Helicenes represent unique 3D aromatic systems which are inherently chiral. Such features predetermine their use in enantioselective catalysis, molecular recognition, nonlinear optics, molecular electronics and photonics, or their use as liquid crystals or components for molecular devices. From a practical point of view, most helicenes are chemically stable, sufficiently soluble in organic solvents, and resistant to configurational scrambling.

helicene



Several studies are underway to extend the helicene syntheses so they yield functionalized helicenes, heterohelicenes, higher homologues, helicenes that are nonracemic, and helicene-like congeners.


Current and Proposed Projects

  • Synthesis of functionalized helicenes/heterohelicenes
  • Preparation of optically pure helicenes/heterohelicenes
  • Application of helicene/heterohelicene-based ligands to enantioselective catalysis
  • Preparation of helicene/heterohelicene-based components for molecular electronics and photonics
  • Helicene-based materials for molecular recognition and catalysis
  • Synthesis of helicenes for bioapplications
  • Physical and quantum chemical studies on helicenes

Examples of envisioned targets

 

helicenes