Journal
TETRAHEDRON
Volume 65, Issue 35, Pages 7249-7258Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.02.055
Keywords
Cucurbituril; Diffusion ordered spectroscopy; Supramolecular chemistry; Polymers
Categories
Funding
- National Science Foundation [CHE-0615049]
- Department of Education [P200A060238-07]
- GAANN
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We describe the synthesis of a series of guests (1-6) containing two adamantylammonium ions separated by xylylene spacing groups and their complexation properties toward double cavity cucurbituril host bis-ns-CB[10]. We observed the preferential formation of 1:1, 2:2, and oligomeric complexes rather than the desired n:n supramolecular polymers. Guest 7, which contains a longer biphenyl spacer successfully precludes the formation of the 1:1 complex but results in the formation of the 2:2 complex (bis-ns-CB[10](2).7(2)) rather than supramolecular polymer. Guest 8, which contains adamantylammonium, p-xylylene diammonium, and hexanediammonium ion binding regions is shown to reversibly form 2:2 and 1:2 complexes (bis-ns-CB[10](2).8(2) and bis-ns-CB[10].8(2)) in response to changes in host:guest stoichiometry. Lastly, this equilibrium can be manipulated by the addition of exogenous CB[6], which selectively targets the hexanediammonium ion binding region of 8 and delivers the penta-molecular complex bis-ns-CB[10].8(2)-CB[6](2). (C) 2009 Elsevier Ltd. All rights reserved.
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