My research in 180 words by Clara Testard, doctoral student in the GOBS team

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Synthesis and study of asymmetric bridged cyclodextrins for chiral recognition applications

Cyclodextrins are natural macrocycles obtained by the enzymatic degradation of starch. Soluble in water but possessing a hydrophobic cavity, cyclodextrins are renowned for their ability to form inclusion complexes with apolar compounds. In our team, a methodology for the selective functionalization of the primary crown of cyclodextrins has enabled their chemical modification and modulation of their properties.

© IPCM

My thesis work, carried out at the IPCM under the supervision of Prof. Matthieu Sollogoub, focuses on asymmetric cyclodextrin cavity bridging, and how this influences the shape and recognition properties of cyclodextrin. The aim of my work is to access two asymmetric, mirror-image cavities.

To this end, I have synthesized two regioisomers of cyclodextrins bridged by a tripodal motif, together with the corresponding copper complexes.
Using UV-visible spectroscopy, I measured the association constants between these encapsulated copper complexes and a series of chiral carboxylates. I was thus able to observe opposite enantioselectivities in favor of one or other of the “guest” carboxylate pair, depending on the “host” cyclodextrin regioisomer used.

Contact : Clara Testard