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- Title
Neutral and Anionic Guests and Their Effect on the Formation of Pseudorotaxanes by Using a Flexible Tetracationic Imidazolium Macrocycle.
- Authors
Gong, Han-Yuan; Rambo, Brett M.; Lynch, Vincent M.; Keller, Karin M.; Sessler, Jonathan L.
- Abstract
The ability to control and direct molecular assembly has important implications in the design of environmentally responsive materials. Reported here is the use of competitive neutral- and anionic-guest recognition to control the formation, disruption, replacement-based construction and higher-order assembly properties of pseudorotaxane structures involving a large, cationic tetraimidazolium receptor. In particular, we showed that the chloride anion (as the tetrabutylammonium (TBA+) salt) serves to replace directly the 2,6-naphthalene dicarboxylate dianion from the preformed complex, involving this dianion. In contrast, the addition of the nitrate anion (as the TBA+ salt) serves to effect displacement of a pre-bound 2,6-naphthalene dicarboxylate dianion in a stepwise manner allowing for stabilization of a so-called 'outside'-binding mode under appropriate conditions. We have also found that by using biphenyl-3,4,3′,4′-tetraamine as the guest, a 1D-donor-acceptor-donor coordination polymer can be stabilized, whereas the addition of 6-amino-naphthalene-2-sulfonate anion to the pre-formed complex between the tetraimidazolium receptor and the 2,6-naphthalene dicarboxylate dianion produces a new pseudorotaxane complex. This guest-based competition and subsequent molecular translocation is supported by solution-state NMR spectroscopic studies as well as solid-state single-crystal X-ray structural analyses. The results described herein provide initial evidence that guest competition can be used to control molecular 'switching' and substrate binding within an appropriately designed anion receptor.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 25, p7803
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201200304