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

2018; Wiley; Volume: 131; Issue: 1 Linguagem: Inglês

10.1002/ange.201811561

1521-3757

Chuan‐Zhi Liu, Satish Koppireddi, Hui Wang, Dan‐Wei Zhang, Zhan‐Ting Li,

Supramolecular Chemistry and Complexes

Abstract 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 CF 2 I 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 ICF 2 CF 2 I 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.