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Self‐Assembling Cyclophanes and Catenanes Possessing Elements of Planar Chirality
Author(s) -
Ashton Peter R.,
Boyd Sue E.,
Menzer Stephan,
Pasini Dario,
Raymo Françisco M.,
Spencer Neil,
Stoddart J. Fraser,
White Andrew J. P.,
Williams David J.,
Wyatt Paul G.
Publication year - 1998
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/(sici)1521-3765(19980210)4:2<299::aid-chem299>3.0.co;2-z
Subject(s) - catenane , planar chirality , chemistry , cyclophane , chirality (physics) , crystallization , crystallography , enantiomer , stereochemistry , planar , molecule , organic chemistry , physics , crystal structure , enantioselective synthesis , nambu–jona lasinio model , chiral symmetry breaking , computer graphics (images) , quantum mechanics , quark , computer science , catalysis
Spontaneous resolution upon crystallization A cyclophane and two [2]catenanes possessing elements of planar chirality have been self‐assembled in good yields. In particular, the [2]catenane (right) incorporating cyclobis(paraquat‐1,5‐naphthalene) and bis‐1/5‐dioxynaphtho[38]crown‐10, possesses four elements of planar chirality and can exist as a mixture of six diastereoisomeric pairs of enantiomers, a total of twelve stereoisomers. However, spontaneous resolution occurs upon crystallization and only one out of the twelve possible stereoisomers is observed in the solid state.