As shown by us earlier, the major diastereomer formed in the metal-mediated Barbier-allylation of D-mannose adopts a linear conformation both in solid state and in solution. Unusual for small molecular polyol, this compound spontaneously forms hydrogen-bonded networks and self-aggregates from aqueous solution upon stirring.<br/><br/>We present here a thorough study of the solid state structures of both the allylated D-mannose and its racemic form, likewise showing self-agglomerating behavior in water solution. Binary melting point diagrams were determined by differential scanning calorimetry (DSC) analysis of recrystallized samples in varying enantiomeric ratios. These results, together with powder X-ray diffraction analysis, confirm that the allylated mannose forms a true racemate. In addition, both the enantiopure and racemic allylated mannoses were subjected to polymorphism analysis by DSC, XRPD and CP MAS <sup>13</sup>C NMR spectroscopy. The results indicate polymorphism in both modifications. Single crystal X-ray structure of one of the racemic polymorphs was determined and is discussed together with the potential use of these small self-assembling molecular rods in possible material science applications.

Thermal, crystallographic and spectroscopic studies on enantiomerically pure and racemic allylated mannoses showing self-assembling properties

255th National Meeting (2018)

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