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Chiral [1]Rotaxanes: X‐Ray Structures and Chiroptical Properties
Author(s) -
Reuter Carin,
Seel Christian,
Nieger Martin,
Vögtle Fritz
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000315)83:3<630::aid-hlca630>3.0.co;2-1
Subject(s) - rotaxane , chemistry , chromophore , molar ratio , sulfonamide , stereochemistry , crystallography , polymer chemistry , organic chemistry , molecule , supramolecular chemistry , catalysis
New chiral [1]rotaxanes with aromatic bridges were prepared in yields up to 72% starting from a [2]rotaxane with sulfonamide groups in wheel and axle. The X‐ray structures of the parent [2]rotaxane 1 and of the three [1]rotaxanes 3e , g , h were solved which show networks of H‐bonds between wheel and axle. The separation of the racemic mixtures of four of the [1]rotaxanes, i.e. , of 3a , b , d , e , was possible with HPLC on Chiralcel OD . The aromatic chromophores in the bridges lead to a considerable enhancement of the intensities of the molar CD as compared to the analogues with aliphatic bridges. In one case ( 3d ), the Cotton effects are as strong as those usually found in helicenes.