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Ureido pyrimidinedione derivatives with phenyl, 1-naphthyl and 2-naphthyl substituents form stable dimers via quadruple hydrogen bonding, but the 1-naphthyl derivative presents an unexpected tautomer in the solid state.
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http://dx.doi.org/10.1039/b717285k | DOI Listing |
Angew Chem Int Ed Engl
September 2016
Key Laboratory of Molecular Nanostructure and Nanotechnology, Institute of Chemistry, Chinese Academy of Sciences and Beijing National Laboratory for Molecular Sciences, Beijing, 100190, P.R. China.
A series of self-complementary ureido pyrimidinedione (UPy) derivatives modified with different aurophilic anchoring groups were synthesized. Their electron transport properties through the quadruple hydrogen bonds in apolar solvent were probed employing the scanning tunneling microscopy break junction (STMBJ) technique. The molecule terminated with a thiol shows the optimal electron transport properties, with a statistical conductance value that approaches 10(-3) G0 .
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December 2014
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5, Takayama, Ikoma, Nara 6300192, Japan.
Quadruple hydrogen-bonding interactions stabilized the mixed-valence states of dimers of triarylamine derivatives bearing an ureido pyrimidinedione moiety without any electronic coupling. This study represents the first example of proton-coupled "organic" mixed valency in solution with different substituents being used to control the stability.
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March 2008
Center for Supramolecular Science and Department of Chemistry, University of Miami, Coral Gables, FL 33124-0431, USA.
Ureido pyrimidinedione derivatives with phenyl, 1-naphthyl and 2-naphthyl substituents form stable dimers via quadruple hydrogen bonding, but the 1-naphthyl derivative presents an unexpected tautomer in the solid state.
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