Journal
CRYSTENGCOMM
Volume 10, Issue 12, Pages 1782-1789Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b811462e
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Funding
- UK Engineering and Physical Sciences Research Council (EPSRC) [GR/S97521/01, EP/D048761/1]
- European Union [NMP4-CT-2004-013817]
- EPSRC [EP/D048761/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/D048761/1, GR/S97521/01] Funding Source: researchfish
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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 R2/2(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 center dot center dot center dot 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.
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