This work describes the design and synthesis of a set of four organic molecules that are intended to hydrogen-bond to each other in a pairwise manner. The four hydrogen-bonding units, termed ‘A’, ‘B’, ‘C’ and ‘D’, when placed in solution together, are designed so that A binds only to B, and C binds only to D. Each unit does not bind to itself, nor to either of the other two units to which binding is not intended. For example, A binds to B, but not to A, C, or D. Each unit contains an array of four hydrogen-bonds for strong binding to its partner, is designed to be as rigid as possible, as non-tautomeric as possible, and utilises a staggered non-symmetrical architecture. Of the four intended compounds, three were successfully synthesised (A, B and D). Units B and D were soluble in CDCl<sub>3</sub>, but Unit A was not. Therefore, the design and synthesis of Unit A was amended, and two variants of Unit A that are both soluble in CDCl<sub>3</sub> were successfully synthesised. <sup>1</sup>H NMR binding experiments were performed between Unit B and each of the two variants of Unit A. Their binding behaviour was described. A binding constant could not be calculated because the units did not bind in a 1:1 fashion.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:627783 |
| Date | January 2013 |
| Creators | Pearson, Jem M. |
| Contributors | Anderson, Edward A. |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:f0630898-35b4-4c74-bc31-dfd252c2ee26 |
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