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Issue 12, 2008
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Hydrogen-bonding tectons for the construction of bimolecular framework materials

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Abstract

Three hydrogen-bonding tectons functionalised with pyrimidine-dione hydrogen-bonding moieties, either uracil or thymine groups, have been synthesised and their solid-state structures studied by single crystal X-ray diffraction. The tectons have different linkers between the pyrimidine-dione hydrogen-bonding groups. Whereas tectons 1 and 2 have either naphthalenetetracarboxylic diimide or p-xylyl spacers, respectively, linking two hydrogen-bonding appendages, tecton 3 comprises three thymine moieties linked via a 2,4,6-tris(methyl)mesitylene spacer. All three tectons have been structurally characterised and in the case of 2 and 3 exhibit the anticipated R22(8) double hydrogen-bonded arrangement between the imide moieties. In contrast, the single crystal structure of the DMSO solvate of 1 does not exhibit inter-tecton hydrogen-bonding but adopts N–H⋯O interactions with guest DMSO molecules. However, bimolecular hydrogen-bonded adducts have successfully been prepared exploiting the complementary triple hydrogen-bonding interactions between 1, or 2, and melamine to give two-dimensional hydrogen-bonded sheets.

Graphical abstract: Hydrogen-bonding tectons for the construction of bimolecular framework materials

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Article information


Submitted
07 Jul 2008
Accepted
31 Jul 2008
First published
02 Sep 2008

CrystEngComm, 2008,10, 1782-1789
Article type
Paper

Hydrogen-bonding tectons for the construction of bimolecular framework materials

J. Hamblin, S. P. Argent, A. J. Blake, C. Wilson and N. R. Champness, CrystEngComm, 2008, 10, 1782
DOI: 10.1039/B811462E

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