Hydrogen-bonding tectons for the construction of bimolecular framework materials

Hamblin, J., Argent, S. P., Blake, A. J., Wilson, C. and Champness, N. R. (2008) Hydrogen-bonding tectons for the construction of bimolecular framework materials. CrystEngComm, 10(12), pp. 1782-1789. (doi: 10.1039/B811462E)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Wilson, Dr Claire
Authors: Hamblin, J., Argent, S. P., Blake, A. J., Wilson, C., and Champness, N. R.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:CrystEngComm
Publisher:Royal Society of Chemistry
ISSN:1466-8033
Published Online:02 September 2008

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