Directed crystal growth of polymorphic compounds is critical for the production of pharmaceuticals and other patentable materials. To that end, surfaces may be tailored using self-assembled monolayers (SAMs) and used to selectively nucleate and grow specific polymorphs. Siloxane SAMs on glass surfaces have been previously demonstrated to direct the growth of compounds including 1,3-bis(<i>m</i>-cyanophenyl) urea (mCyPU) from a variety of solvents. Here, high-performance liquid chromatography (HPLC) using tailored stationary phases was employed in order to better understand the polymorph selection process. A library of HPLC stationary phases was prepared by functionalizing 5 μm silica particles with a variety of trimethoxysilanes. The resulting particles mimic the 2-D SAM surfaces used in bulk growth studies. After packing the particles into 25-cm columns, mCyPU retention time data were collected using a variety of mobile phase solvents over a range of temperatures. Differential interactions between mCyPU and the functionalized silica manifest as peak shifts in the chromatograms. Thermodynamic parameters calculated from the chromatograms were compared to bulk crystallization results.

Chromatographic investigation of the interaction between the polymorphic compound mCyPU and tailored surface

251st National Meeting (2016)

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