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Homochiral Double Helicates Based on Cyclooctatetrathiophene: Chiral Self‐Sorting with the Intramolecular S⋅⋅⋅N Interaction
Author(s) -
Tian Yu,
Wang Guangxia,
Ma Zhiying,
Xu Li,
Wang Hua
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803948
Subject(s) - enantiopure drug , intramolecular force , chemistry , stereochemistry , enantiomer , thiophene , chiral column chromatography , ligand (biochemistry) , supramolecular chemistry , chiral ligand , chiral resolution , pyridine , crystal structure , crystallography , enantioselective synthesis , medicinal chemistry , receptor , organic chemistry , catalysis , biochemistry
The design and synthesis of homochiral double helicates are reported that are constructed by means of Ag‐induced supramolecular self‐sorting of saddle‐shaped cyclooctatetrathiophene‐based pyridine ligands ( 1 and 2 ). The intramolecular S⋅⋅⋅N interaction ensures that the thiophene and pyridine rings of ligands 1 and 2 are in coplanar and syn ‐locked structures. In the presence of Ag + , the racemic ligands 1 and 2 only afforded homochiral double helicates, indicating effective chiral self‐sorting process under the influence of the S⋅⋅⋅N interaction. The X‐ray crystal structure of 1 2 Ag 2 reveals a pair of homochiral double helicates ( R,R,R,R )‐ 1 2 Ag 2 and ( S,S,S,S )‐ 1 2 Ag 2 . Furthermore, chiral resolution of racemic ligand 1 was achieved by chiral‐phase HPLC, and the enantiomers and their corresponding enantiopure Ag complexes were characterized.