The DOI matches its Crossref record; 21 of the 21 references it cites were found in a registry or an index.
Molecular Tweezers and Clips as Synthetic Receptors. Molecular Recognition and Dynamics in Receptor−Substrate Complexes
Abstract
The molecular tweezers (1, 2) and clips (3-7) containing naphthalene and benzene spacer units can be synthesized via repetitive Diels-Alder reactions by the use of a molecular "Lego" set consisting of bisdienophiles (8, 9, 14) and dienes (10, 13). The new receptors selectively bind electron-deficient neutral and cationic substrates in solution. Only the benzene-spaced tweezers form complexes with aliphatic substrates, whereas the other receptors bind aromatic substrates preferentially. HPLC studies with 1 and 2 chemically bonded to stationary phases give similar results for the heterogeneous systems. The formation of stable complexes between the water-soluble clip 5g and N-alkylpyridinium cations, such as N-methylnicotinamide and NAD(+), in aqueous solution illustrates the importance of the hydrophobic effect for arene-arene interactions. The dynamics of the complex formation and substrate mobility were investigated by the use of temperature-dependent liquid- and solid-state NMR spectroscopy. The electrostatic potential surface (EPS) of 1-7 is calculated to be surprisingly negative on the concave side of each molecule and, hence, complementary to the EPS of the electron-deficient substrates, suggesting that the attractive receptor-substrate interaction is here of predominantly electrostatic nature.
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Metadata
- Authors
- Klärner, F.-G., & Kahlert, B.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-18
- Volume
- 36
- Issue
- 12
- Pages
- 919-932
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2145572439
- Cited by
- 375
- References
- 21
- FWCI
- 9.16
- Type
- journal article
- Language
- en
- Open access
- closed
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