Novel Imidazole Liquid Crystals; Experimental and Computational Approaches
The liquid crystalline materials named (<i>E</i>)-4-(2-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)phenyl and 4-(alkoxy)benzoate, <b>In</b>, were synthesized and their mesomorphic behaviors were examined. The chemical structures of the produced co...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/14/4607 |
| _version_ | 1797444756280705024 |
|---|---|
| author | Nada S. Al-Kadhi Fowzia S. Alamro Saheed A. Popoola Sobhi M. Gomha Noha S. Bedowr Shahd S. Al-Juhani Hoda A. Ahmed |
| author_facet | Nada S. Al-Kadhi Fowzia S. Alamro Saheed A. Popoola Sobhi M. Gomha Noha S. Bedowr Shahd S. Al-Juhani Hoda A. Ahmed |
| author_sort | Nada S. Al-Kadhi |
| collection | DOAJ |
| description | The liquid crystalline materials named (<i>E</i>)-4-(2-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)phenyl and 4-(alkoxy)benzoate, <b>In</b>, were synthesized and their mesomorphic behaviors were examined. The chemical structures of the produced compounds were confirmed by Fourier-transform infrared spectroscopy (FT-IR), NMR, and elemental analysis. Differential scanning calorimetry (DSC) and polarized optical microscopy were used to investigate the mesomorphic properties of designed heterocyclic derivatives. All the compounds tested had suitable thermal stability and enantiotropic behavior of smectogenic temperature ranges. Furthermore, the enantiotropic smectic C phases were observed to cover all the homologues. Moreover, computational investigations corroborated the experimental findings of the mesomorphic behavior. The reactivity parameters were computed for the derivatives and linked with the experimental data. Theoretical calculations revealed that the polarizability of the studied series increases with the chain length, whereas the HOMO–LUMO energy gap or other reactivity descriptors were less sensitive to the size of the system. On the other hand, the predicted thermodynamic parameters revealed the size dependence of thermal stability of the compounds. |
| first_indexed | 2024-03-09T13:17:07Z |
| format | Article |
| id | doaj.art-0f15fde4ed7b45eaa33e6ca1940e9aa0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T13:17:07Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0f15fde4ed7b45eaa33e6ca1940e9aa02023-11-30T21:34:34ZengMDPI AGMolecules1420-30492022-07-012714460710.3390/molecules27144607Novel Imidazole Liquid Crystals; Experimental and Computational ApproachesNada S. Al-Kadhi0Fowzia S. Alamro1Saheed A. Popoola2Sobhi M. Gomha3Noha S. Bedowr4Shahd S. Al-Juhani5Hoda A. Ahmed6Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaChemistry Department, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi ArabiaChemistry Department, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi ArabiaChemistry Department, College of Sciences, Taibah University, Yanbu 30799, Saudi ArabiaChemistry Department, College of Sciences, Taibah University, Yanbu 30799, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Cairo University, Cairo 12613, EgyptThe liquid crystalline materials named (<i>E</i>)-4-(2-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)phenyl and 4-(alkoxy)benzoate, <b>In</b>, were synthesized and their mesomorphic behaviors were examined. The chemical structures of the produced compounds were confirmed by Fourier-transform infrared spectroscopy (FT-IR), NMR, and elemental analysis. Differential scanning calorimetry (DSC) and polarized optical microscopy were used to investigate the mesomorphic properties of designed heterocyclic derivatives. All the compounds tested had suitable thermal stability and enantiotropic behavior of smectogenic temperature ranges. Furthermore, the enantiotropic smectic C phases were observed to cover all the homologues. Moreover, computational investigations corroborated the experimental findings of the mesomorphic behavior. The reactivity parameters were computed for the derivatives and linked with the experimental data. Theoretical calculations revealed that the polarizability of the studied series increases with the chain length, whereas the HOMO–LUMO energy gap or other reactivity descriptors were less sensitive to the size of the system. On the other hand, the predicted thermodynamic parameters revealed the size dependence of thermal stability of the compounds.https://www.mdpi.com/1420-3049/27/14/4607imidazole liquid crystalsmesomorphic propertiessmectic phaseDFToptimized structures |
| spellingShingle | Nada S. Al-Kadhi Fowzia S. Alamro Saheed A. Popoola Sobhi M. Gomha Noha S. Bedowr Shahd S. Al-Juhani Hoda A. Ahmed Novel Imidazole Liquid Crystals; Experimental and Computational Approaches Molecules imidazole liquid crystals mesomorphic properties smectic phase DFT optimized structures |
| title | Novel Imidazole Liquid Crystals; Experimental and Computational Approaches |
| title_full | Novel Imidazole Liquid Crystals; Experimental and Computational Approaches |
| title_fullStr | Novel Imidazole Liquid Crystals; Experimental and Computational Approaches |
| title_full_unstemmed | Novel Imidazole Liquid Crystals; Experimental and Computational Approaches |
| title_short | Novel Imidazole Liquid Crystals; Experimental and Computational Approaches |
| title_sort | novel imidazole liquid crystals experimental and computational approaches |
| topic | imidazole liquid crystals mesomorphic properties smectic phase DFT optimized structures |
| url | https://www.mdpi.com/1420-3049/27/14/4607 |
| work_keys_str_mv | AT nadasalkadhi novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT fowziasalamro novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT saheedapopoola novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT sobhimgomha novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT nohasbedowr novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT shahdsaljuhani novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches AT hodaaahmed novelimidazoleliquidcrystalsexperimentalandcomputationalapproaches |