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Issue 25, 2014
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New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: synthesis, liquid crystalline behavior and photo physical properties

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Abstract

A new series of luminescent 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles containing three ring systems, viz. methoxy pyridine, benzonitrile and alkoxy benzene with variable alkoxy chain length, with bent-core structures were synthesized as potential mesogens and characterized by spectral techniques. Their liquid crystalline behavior was investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and variable temperature powder X-ray diffraction (PXRD) measurements. The study reveals that compounds with shorter chain lengths [i.e. m = 4] exclusively exhibit the nematic phase while compounds with longer chain lengths [i.e. m = 6–14 (only even)] show predominantly the orthorhombic columnar phase. Single crystal X-ray analysis of 4-(2-(4-butyloxy/octyloxyphenyl)-6-methoxypyridin-4-yl)benzonitriles reveals that they possess slightly non-planar unsymmetrical bent structures and their molecular packing consists of nonconventional H-bond interactions; it also explains the observed liquid crystalline phase. An optical study indicates that the title compounds are good blue emitting materials showing absorption and emission bands in the range 335–345 nm and 415–460 nm, respectively. An electrochemical study of 4-(2-(4-octyloxyphenyl)-6-methoxypyridin-4-yl)benzonitrile shows a band gap of 1.89 eV with HOMO and LUMO energy levels of −5.06 and −3.17 eV, respectively. Also, density functional theory (DFT) calculations confirm its optimized geometry, electronic absorption and frontier molecular orbital distributions.

Graphical abstract: New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: synthesis, liquid crystalline behavior and photo physical properties

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The article was received on 17 Jan 2014, accepted on 09 Mar 2014 and first published on 10 Mar 2014


Article type: Paper
DOI: 10.1039/C4CE00128A
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CrystEngComm, 2014,16, 5573-5582

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    New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: synthesis, liquid crystalline behavior and photo physical properties

    T. N. Ahipa, V. Kumar, D. S. Shankar Rao, S. K. Prasad and A. V. Adhikari, CrystEngComm, 2014, 16, 5573
    DOI: 10.1039/C4CE00128A

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