Halogen Bonding Directed Supramolecular Quadruple and Double Helices from Hydrogen‐Bonded Arylamide Foldamers

• Published in: Angewandte Chemie International Edition Vol. 58; no. 1; pp. 226 - 230
• Main Authors: Liu, Chuan‐Zhi, Koppireddi, Satish, Wang, Hui, Zhang, Dan‐Wei, Li, Zhan‐Ting
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 02-01-2019
• Edition: International ed. in English
• Subjects: Bearing; Fluorination; foldamers; halogen bonding; helical structures; Helices; hydrogen bonding; Pyridines; self-assembly; hydrogen bonding; self-assembly; halogen bonding; helical structures; foldamers
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201811561

Halogen bonding has been used to glue together hydrogen‐bonded short arylamide foldamers to achieve new supramolecular double and quadruple helices in the solid state. Three compounds, which bear a pyridine at one end and either a CF2I or fluorinated iodobenzene group at the other end, engage in head‐to‐tail N⋅⋅⋅I halogen bonds to form one‐component supramolecular P and M helices, which stack to afford supramolecular double‐stranded helices. One of the double helices can dimerize to form a G‐quadruplex‐like supramolecular quadruple helix. Another symmetric compound, which bears a pyridine at each end, binds to ICF2CF2I through N⋅⋅⋅I halogen bonds to form two‐component supramolecular P and M helices, with one turn consisting of four (2+2) molecules. Half of the pyridine‐bearing molecules in two P helices and two M helices stack alternatingly to form another supramolecular quadruple helix. Another half of the pyridine‐bearing molecules in such quadruple helices stack alternatingly with counterparts from neighboring quadruple helices, leading to unique quadruple helical arrays in two‐dimensional space.
Glued in place: Halogen bonds glue together short hydrogen‐bonded arylamide molecules to form either one‐ or two‐component helices. The helices stack to produce supramolecular quadruple and double helical structures.