PhD Project Title: Asymmetric C(sp2)-H activation for the synthesis original materials
Principal Investigator: Dr. Joanna Wencel-Delord
PhD Project description: Axial chirality is an appealing and intriguing feature of many natural products, biologically active molecule and privileged ligands. However, axial chirality has been rarely implemented in the design of original chiral materials. Recently, our laboratory has developed an original methodology allowing synthesis of axially chiral biaryls via diastereoselective C-H activation. This strategy is very general, stereoselective and allows straightforward synthesis of a diversity of axially chiral biaryls. This approach will now be applied to prepare unprecedented axially chiral polyaromatic hydrocarbons as well as stereogenic molecular organic frameworks
Description of the work: The PhD student will initially apply the sulfoxide-directed C(sp2)-H activation to functionalize perylene and corannulene-type scaffolds (collaboration with Prof. D. Gryko, Warsaw, Poland). Thus accessed PAHs bearing axial chiral units will be characterized and their optoelectonic properties will be investigated. In parallel, axially chiral biaryls, such as derivatives of [1,1′-biphenyl]-4,4′-dicarboxylic acid, will be synthesized and used as unique building blocks to construct chiral MOFs (in collaboration with Prof. A. Kirillov). These chiral materials will be evaluated as stereogenic heterogeneous catalysts for direct functionalization of terpenes.
Relevant skills that will be considered are:
- Strong theoretical background and practical skills in organic synthesis and catalysis
- Experience and theoretical background in the synthesis of materials will be an advantage
- Practical experience in analytical methods (NMR, MS, HPLC)
- Good level of English proficiency (understood, spoken and written)
- Skills in scientific writing (reports, papers, etc.)
- Team spirit and collaborative predisposition
Planned secondments: “1 secondment (3 months) in the group of Prof. Gryko (Poland), 1 secondment in Merck (Germany) and 1 secondment in the group of Prof. A. Kirillov (Portugal).
 Jerhaoui, S.; Djukic, J.-P.; Wencel-Delord, J.; Colobert, F. ACS Catal. 2019, 9, 2532–2542.