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Halogen Bonding Directed Supramolecular Quadruple and Double Helices from Hydrogen‐Bonded Arylamide Foldamers
Author(s) -
Liu ChuanZhi,
Koppireddi Satish,
Wang Hui,
Zhang DanWei,
Li ZhanTing
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811561
Subject(s) - supramolecular chemistry , chemistry , crystallography , helix (gastropod) , hydrogen bond , molecule , stereochemistry , pyridine , halogen , halogen bond , supramolecular assembly , crystal structure , organic chemistry , ecology , alkyl , snail , biology
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.