Patrick Schanen

 

Postdoctoral Fellow

Location:

HCI G-312

Phone:

+41-44-633 4169

e-mail:

Patrick Schanen

Education

1993-1995:

B.Sc. (Chemistry) Université catholique de Louvain, Belgium

1995-1997:

M.Sc. (Chemistry) Université catholique de Louvain, Belgium

1997-2003:

Ph.D. (organic Chemistry) under the supervision of Prof. L. Ghosez, Université catholique de Louvain, Belgium, title "Asymmetric cyclopentannulation reactions: scope and limitation"

2003-2005:

post-doc with Prof. C.-H. Wong, Scripps Research Institute, La Jolla, CA, USA

since 2006:

post-doc with Prof. F. Diederich, ETH-Zürich

Project

Highly unsaturated carbon-rich organic materials have shown interesting optical and electrochemical behavior. Larger structures of these materials have been built from molecular units such as diethynylethenes (DEEs) and tetraethynylethenes (TEEs). In this objective, diethyleneallenes (DEAs) are particularly interesting, as they are no longer planar but show a 90° twist due to the cumulenic bond. Thus they are axially chiral and the inherent p-electron conjugation is interrupted. If these compounds could be synthesized in an enantiopure form interesting 3-dimensional structures, such as helixes could be envisioned.
In this project we will try to develop a methodology to synthesize DEAs in high optical purity.


Different strategies can be applied for the synthesis of enantiomerically pure allenes:
- In a first approach, one could synthesize the target compounds in a racemic form and separate the enantiomers by HPLC. While this method is time- and solvent-consuming, it offers the advantage of yielding both enantiomers in only one reaction sequence.
- In a second method, the precursors for the allenes could be synthesized in an optically pure form. Hopefully the reaction leading to the allene would conserve the chiral information and yield the optically pure allene.
These chiral building blocks will then be used to construct novel supramolecular structures, with a special emphasis on the construction of new helical structures.

last update: Mai 2006