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Template‐Directed Synthesis of a Rotacatenane
Author(s) -
Amabilino David B.,
Ashton Peter R.,
Bravo José A.,
Raymo Françisco M.,
Stoddart J. Fraser,
White Andrew J. P.,
Williams David J.
Publication year - 1999
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/(sici)1099-0690(199906)1999:6<1295::aid-ejoc1295>3.0.co;2-z
Subject(s) - catenane , chemistry , supramolecular chemistry , molecule , dumbbell , crystallography , stereochemistry , molecular machine , nanotechnology , crystal structure , organic chemistry , materials science , medicine , physical therapy
A [2]catenane, able to bind π‐electron‐rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so‐called rotacatenane – i.e., a molecule composed of a dumbbell‐shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single‐crystal X‐ray analyses. Furthermore, some of the co‐conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable‐temperature 1 H‐NMR spectroscopy.