Przemyslaw Gawel

 

PhD Student

Location:

HCI G-312

Phone:

+41-44-632 2998

e-mail:

Przemyslaw Gawel

Education

2005-2006:

Inter-Faculty Individual Studies in Mathematics and Natural Sciences at University of Warsaw (UW), Poland.

2010:

Bachelor Thesis in Biotechnology with M. Adamczyk-Poplawska, UW.

2011:

Diploma Thesis in Chemistry with T. Bauer, UW.

2010-2011:

Visiting Researcher with H. Hopf, Technische Universität Braunschweig, Germany. In cooperation with H. Dodziuk.

since 2012:

Graduate Student with F. Diederich, ETH Zurich.

 

Functional Cumulene-Based Molecular Materials

The central double bond in [3]cumulenes exhibits triple bond character, both in its length and reactivity. These similarities result from the identical sp-hybridization of carbon atoms composing them. Recently we provided a comprehensive support for the proacetylenic structure and reactivity of [3]cumulenes both by experimental and theoretical studies. The proacetylenic reactivity of [3]cumulenes is highly dependent on the polarity of the starting material. While in the reaction with TCNE the highly polarized push–pull [3]cumulenes give stable zwitterions, the symmetric tetraaryl[3]cumulenes yield, after the reaction cascade, 5,11-diphenyl-tetracenes. We are currently studying new reactivities of cumulenes and investigating optoelectronic properties of these new chromophores.

Cumulenes, as well as the other chromophores obtained from them, have potential use in OLEDs, organic photodetectors and even in organic solar cells. Organic electronic systems are lighter, more flexible, less expensive, and friendlier to the environment than inorganic ones.


Publications

T. Bauer, S. Smoliński, P. Gaweł, J. Jurczak, Tetrahedron Lett. 2011, 52, 4882-4884. Enantioselective addition of phenylacetylene to aldehydes catalyzed by a d-glucosamine-derived sulfonamide–titanium complex.

H. Dodziuk, V. Vetokhina, H. Hopf, R. Luboradzki, P. Gaweł, J. Waluk, J. Chem. Phys. 2012, 136, 074201. Electronic states of cyclophanes with small bridges.

P. Gawel, C. Dengiz, A. D. Finke, N. Trapp, C. Boudon, J.-P. Gisselbrecht, F. Diederich Angew. Chem. 2014, 126, 4430–4434; Angew. Chem. Int. Ed. 2014, 53, 4341–4345. Synthesis of Cyano-Substituted Diaryltetracenes from Tetraaryl[3]cumulenes. (Highlighted in Synfacts 2014; 10(6) 587).

P. Gawel, Y.-L. Wu, A. D. Finke, N. Trapp, M. Zalibera, C. Boudon, J.-P. Gisselbrecht, W. B. Schweizer, G. Gescheidt, F. Diederich Chem. Eur. J. 2015, 21, 6215–6225. Push-Pull Buta-1,2,3-trienes: Exceptionally Low Rotational Barriers of Cumulenic C=C Bonds and Proacetylenic Reactivity.

Last update: Apr. 2015