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Using “Threading Followed by Shrinking” to Synthesize Highly Stable Dialkylammonium‐Ion‐Based Rotaxanes
Author(s) -
Wang LiangYun,
Ko JiaLing,
Lai ChienChen,
Liu YiHung,
Peng ShieMing,
Chiu ShengHsien
Publication year - 2013
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/chem.201300049
Subject(s) - rotaxane , sulfone , threading (protein sequence) , polymer chemistry , supramolecular chemistry , chemistry , ammonium , dumbbell , materials science , crystallography , organic chemistry , crystal structure , protein structure , medicine , biochemistry , physical therapy
Herein, we report a “threading followed by shrinking” approach for the synthesis of rotaxanes by using an “oxygen‐deficient” macrocycle that contained two arylmethyl sulfone units and the dumbbell‐shaped salt bis(3,5‐dimethylbenzyl)ammonium tetrakis(3,5‐trifluoromethylphenyl)borate as the host and guest components, respectively. The extrusion of SO 2 from both of the arylmethyl sulfone units of the macrocyclic component in the corresponding [2]pseudorotaxane resulted in a [2]rotaxane that was sufficiently stable to maintain its molecular integrity in CD 3 SOCD 3 at 393 K for at least 5 h.