Chalcogen-Bond-Induced Double Helix Based on Self-Assembly of a Small Planar Building Block

Angew Chem Int Ed Engl. 2023 Jul 17;62(29):e202304202. doi: 10.1002/anie.202304202. Epub 2023 Jun 2.

Abstract

As a rule, helical structures at the molecular level are formed by non-planar units. This makes the design of helices, starting from planar building blocks via self-assembly, even more fascinating. Until now, however, this has only been achieved in rare cases, where hydrogen and halogen bonds were involved. Here, we show that the carbonyl-tellurium interaction motif is suitable to assemble even small planar units into helical structures in solid phase. We found two different types of helices: both single and double helices, depending on the substitution pattern. In the double helix, the strands are connected by additional Te⋅⋅⋅Te chalcogen bonds. In the case of the single helix, a spontaneous enantiomeric resolution occurs in the crystal. This underlines the potential of the carbonyl-tellurium chalcogen bond to generate complex three-dimensional patterns.

Keywords: Chalcogen Bond; DFT Calculations; Double Helix; Self-Assembly.