Synthetic molecules for biomimetic information handling
Final Report Abstract
During this fellowship, we were able to identify a scaffold derived from iodinated contrast agents, which existed as two conformers rapidly interconverting at room temperature. This design overcame to some extent solubility issues that plagued the originally planned planar hydrogen-bonding molecules, but was still not satisfying for obtaining reliable quantitative data on rates of interconversion. We therefore moved to an alternative design featuring a merger of axial and planar chirality. We developed conditions for the synthesis and ring-expansion of anthranilamide derivatives to obtain medium-sized-ring analogues of tricyclic antidepressants. We showed that these products exhibited solvent-dependent ground state chirality and we quantified the rates of enantiomerization and diastereomerization where relevant.
Publications
- “Medium-Sized-Ring Analogues of Dibenzodiazepines by a Conformationally Induced Smiles Ring Expansion”. Angew. Chem. Int. Ed. 2017, 56, 14602-14606
Romain Costil, Quentin Lefebvre, and Jonathan Clayden
