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Chiral Dendrophanes, Dendro[2]rotaxanes, and Dendro[2]catenanes: Synthesis and Chiroptical Phenomena
Author(s) -
Reuter Carin,
Pawlitzki Gregor,
Wörsdörfer Udo,
Plevoets Marcus,
Mohry André,
Kubota Takateru,
Okamoto Yoshio,
Vögtle Fritz
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3059::aid-ejoc3059>3.0.co;2-t
Subject(s) - dendrimer , catenane , chemistry , chirality (physics) , stereochemistry , planar chirality , rotaxane , chiral column chromatography , supramolecular chirality , crystallography , enantioselective synthesis , supramolecular chemistry , enantiomer , organic chemistry , molecule , crystal structure , chiral symmetry , catalysis , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract New chiral dendrimers with planar‐chiral, cycloenantiomeric and topologically chiral cores were prepared in yields of up to 90% starting from a racemic 4‐hydroxy[2.2]paracyclophane, a [2]rotaxane with sulfonamide groups in the wheel and axle positions and [2]catenane with a sulfonamide group in both of its macrocycles. The separation of the racemic mixture of these dendrimers was possible by HPLC on chiral stationary phases. The CD spectra of the dendro[2.2]phanes showed a hitherto unknown influence of the dendritic part on the intensities of the Cotton effects. The chirality of these dendrimers is dependent not only on its chiral elements but also on its dendritic wedges and their generation.