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Synthesis, characterization, investigation of mesomorphic properties and DFT studies of a new 2,5-(dimethoxy)-2-[[(4-(dodecyloxy)phenyl)imino]methyl]benzene): a material liquid crystal for optoelectronics

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Abstract

In this article, synthesis, characterization and mesomorphic properties of a new calamitic liquid crystal, 2,5-(dimethoxy)-2-[[(4-(dodecyloxy)phenyl)imino]methyl]benzene) (DDPIMB) are described. The phase transition temperatures of the DDPIMB mesomorphic compound have been carried out by differential scanning calorimetry and optical polarizing microscopy. Geometry optimization calculations have been made for the two possible isomers as cis and trans of DDPIMB using the DFT/B3LYP/6-311++G(d,p) level of theory. According to the theoretical calculation results, trans isomerism was found more stable than cis isomerism. Therefore, all theoretical calculations were made for the trans-isomer and compared to the observed results. Vibrational assignments of the observed infrared spectra of title compound were carried out based on the calculated potential energy distributions (PEDs). The electronic properties of the DDPIMB were shown on the TD-DFT/B3LYP level. The optical behavior of the liquid crystal DDPIMB was determined through basic optical parameters, nonlinear optics (NLO) properties and dipole moments. Moreover, frontier molecular orbitals and molecular electrostatic potential (MEP) were determined to define the chemical activity of the headline molecule. The obtained results showed that this liquid crystal is a candidate material that can be used in NLO, optics and optoelectronic technology.

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Acknowledgements

This research was supported by TUBITAK. Project Number: 1919BO11602561.

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Authors and Affiliations

  1. Department of Chemical Technology, Banaz Vocational School, Usak University, Usak, Turkey

    Hülya Elmalı Gülbaş

  2. Department of Electrical Electronics Engineering, Faculty of Engineering and Architecture Kırşehir Ahi Evran University, Kırsehir, Turkey

    Emine Tanış

  3. Usak University, Usak, Turkey

    Ali Antepli

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  1. Hülya Elmalı Gülbaş
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  2. Emine Tanış
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Correspondence to Emine Tanış.

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Elmalı Gülbaş, H., Tanış, E. & Antepli, A. Synthesis, characterization, investigation of mesomorphic properties and DFT studies of a new 2,5-(dimethoxy)-2-[[(4-(dodecyloxy)phenyl)imino]methyl]benzene): a material liquid crystal for optoelectronics. J Mater Sci: Mater Electron 31, 15829–15842 (2020). https://doi.org/10.1007/s10854-020-04145-5

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