New columnar liquid crystal materials based on luminescent 2-methoxy-3-cyanopyridines

Abstract

A new series of donor–acceptor–donor (D–A–D) type luminescent mesogens carrying 2-methoxy-3-cyanopyridine as a central core linked with variable alkoxy chain lengths (m = 6 and 8) as terminal substituents was synthesized and characterized using spectral methods. The newly synthesized molecules were subjected to single-crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), differential scanning calorimetric (DSC), polarizing optical microscopy (POM), and fluorescence emission studies in order to ascertain their mesogenic and photophysical properties. The SCXRD data on 4a and 4b reveal that the presence of short intermolecular contacts, viz. C–H···N, C–H···O, C–H···π, and π···π interactions, is responsible for their crystal packing. The measured torsion angle values indicate that molecules possess distorted non-planar structure. The DSC, POM, and PXRD studies confirm that all the molecules show thermotropic liquid crystalline behaviour and exhibit rectangular columnar phase. Further, their UV–visible and fluorescence spectral studies reveal that the target molecules are luminescent displaying a strong absorption band in the range of 335–340 nm and a blue fluorescence emission band in the range of 395–425 nm (both in solution and film state) with good fluorescence quantum yields (10–49 %).