Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 51, Pages 14508-14517Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102128
Keywords
hydrogen bonds; linear arrays; molecular recognition; self-assembly; supramolecular chemistry
Categories
Funding
- Leverhulme Trust [F/00122/AN]
- EPSRC [EP/C007638/1]
- Engineering and Physical Sciences Research Council [EP/C007638/1] Funding Source: researchfish
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Linear arrays of hydrogen bonds are useful for the reversible assembly of stimuli-responsive supramolecular materials. There is thus an ongoing requirement for easy-to-synthesise motifs that are capable of presenting hydrogen-bonding functionality in a predictable manner, such that high-affinity and high-fidelity recognition occurs. The design of linear arrays is made challenging as a consequence of their ability to adopt multiple conformational and tautomeric configurations; with each additional hydrogen-bonding heteroatom added to an array, the available tautomeric and conformational space increases and it can be difficult to anticipate where unproductive conformers/tautomers will arise. This paper describes a detailed study on the complementary ureidoimidazole donor-donor-acceptor (DDA) array (1) and amidoisocytosine donor-acceptor-acceptor (DAA) array (2). A specific feature of 1 is that two degenerate, intramolecular hydrogen-bonded conformations are postulated, both of which present a DDA array that is complementary to appropriate DAA partners. 1D and 2D H-1 NMR spectroscopy, isothermal titration calorimetry, and ab initio structure calculations confirm 1 interacts with 2 (K-a approximate to 33000 M-1 in CDCl3) in a conformer-independent fashion driven by enthalpy. Comparison of the binding behaviour of 1 with hexylamidocytosine (4) and amidonaphthyridine (5) provides insight on the role that intramolecular hydrogen-bonding plays in mediating affinity towards DAA partners.
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