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- Title
Homochiral Double Helicates Based on Cyclooctatetrathiophene: Chiral Self‐Sorting with the Intramolecular S⋅⋅⋅N Interaction.
- Authors
Tian, Yu; Wang, Guangxia; Ma, Zhiying; Xu, Li; Wang, Hua
- Abstract
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 12Ag2 reveals a pair of homochiral double helicates (R,R,R,R)‐12Ag2 and (S,S,S,S)‐12Ag2. Furthermore, chiral resolution of racemic ligand 1 was achieved by chiral‐phase HPLC, and the enantiomers and their corresponding enantiopure Ag complexes were characterized. Asyn‐locked strategy for the design of homochiral double helicates, (R,R,R,R)‐12Ag2 and (S,S,S,S)‐12Ag2, is presented based on chiral self‐sorting by utilizing the intramolecular S⋅⋅⋅N interactions, from chiral saddle‐shaped cyclooctatetrathiophene bearing pyridine groups [(R,R)‐1 and (S,S,)‐1].
- Subjects
CHIRALITY; SUPRAMOLECULAR chemistry; PYRIDINE synthesis; LIGAND analysis; CRYSTAL structure
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 60, p15993
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803948