Important role of molecular packing and intermolecular interactions in two polymorphs of (Z)-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile. Preparation, structures, and optical properties

The novel compound Z-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile (PPyPAN) was synthesized from the condensation reaction between phenylacetonitrile and 4-(pyridin-2-yl)benzaldehyde. This compound crystallizes in two forms: polymorph I (triclinic, P - 1, Z′ = 2) and polymorph II (orthorhombic, Pbc21, Z′ = 2). The molecular structures and optical properties of the two polymorphs have been characterized via 1H NMR, EI, FTIR, UV-Vis spectroscopy, DSC, single-crystal and XRPD. The molecular structure, packing properties, and intermolecular interactions were examined for both polymorphs of PPyPAN in order to interpret the emission properties. A subtle change in the molecular conformation (e.g., a rotation around single CC bonds) found for both polymorph plays an important role in their solid-state properties. The structure and optical properties of the new structures were well characterized and showed unique features for both polymorphic phases. For phase I, we observed an excitation spectrum with an λex at 325-346 nm, which is the maximum excitation or absorption wavelength for the lowest So → S1 transition, which is characteristic to the π-π∗ transition, and an emission spectrum with an λemmax at 454 nm. For phase II, the excitation spectrum showed an λexmax at 325 nm, whereas the λemmax showed a red-shift to 492 nm. © 2014 Elsevier B.V. All rights reserved.

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