2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation
A new liquid crystal series of pyridin-2-yl 4-[4-(alkylphenyl)iminomethyl]benzoate was synthesized and characterized for their mesomorphic behavior. These compounds contain Schiff base and carboxylate ester mesogenic cores, in addition to terminal alkyl chains with a different number of carbons. The...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-06-01
|
| Series: | Crystals |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4352/12/7/902 |
| _version_ | 1827597539016179712 |
|---|---|
| author | Jehan Y. Al-Humaidi Shady Nada Mariam Gerges Marwa Ehab Mariusz Jaremko Abdul-Hamid Emwas Mohamed Hagar |
| author_facet | Jehan Y. Al-Humaidi Shady Nada Mariam Gerges Marwa Ehab Mariusz Jaremko Abdul-Hamid Emwas Mohamed Hagar |
| author_sort | Jehan Y. Al-Humaidi |
| collection | DOAJ |
| description | A new liquid crystal series of pyridin-2-yl 4-[4-(alkylphenyl)iminomethyl]benzoate was synthesized and characterized for their mesomorphic behavior. These compounds contain Schiff base and carboxylate ester mesogenic cores, in addition to terminal alkyl chains with a different number of carbons. The structures were confirmed via FT-IR, and <sup>1</sup>H NMR spectroscopy. The phase transitions were studied by differential thermal analysis (DSC) and the mesophase types were identified by polarized optical microscopy (POM). A comparative study was performed between the synthesized compounds and previously reported compounds. Density functional theory (DFT) calculations were included in the study to compute the dipole moment and the polarizability, as well as the frontier molecular orbitals and the charge distribution mapping, which impact the terminal and lateral interactions of the compounds. The theoretical results were discussed to confirm the experimental data and explain the mesomorphic behavior of the compounds. Finally, the energy gap, global softness, and chemical hardness were calculated to determine the suitability of the liquid crystalline compounds to be employed in applications. |
| first_indexed | 2024-03-09T03:33:50Z |
| format | Article |
| id | doaj.art-b7a32e2177184afaa985b18b35b1ec13 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T03:33:50Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-b7a32e2177184afaa985b18b35b1ec132023-12-03T14:52:09ZengMDPI AGCrystals2073-43522022-06-0112790210.3390/cryst120709022-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT InvestigationJehan Y. Al-Humaidi0Shady Nada1Mariam Gerges2Marwa Ehab3Mariusz Jaremko4Abdul-Hamid Emwas5Mohamed Hagar6Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, EgyptDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, EgyptDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, EgyptSmart-Health Initiative (SHI) and Red Sea Research Center (RSRC), Division of Biological and Environmental Sciences and Engineering (BESE), King Abdullah University of Science and Technology (KAUST), P.O. Box 4700, Thuwal 23955-6900, Saudi ArabiaCore Labs, King Abdullah University of Science and Technology, P.O. Box 4700, Thuwal 23955-6900, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, EgyptA new liquid crystal series of pyridin-2-yl 4-[4-(alkylphenyl)iminomethyl]benzoate was synthesized and characterized for their mesomorphic behavior. These compounds contain Schiff base and carboxylate ester mesogenic cores, in addition to terminal alkyl chains with a different number of carbons. The structures were confirmed via FT-IR, and <sup>1</sup>H NMR spectroscopy. The phase transitions were studied by differential thermal analysis (DSC) and the mesophase types were identified by polarized optical microscopy (POM). A comparative study was performed between the synthesized compounds and previously reported compounds. Density functional theory (DFT) calculations were included in the study to compute the dipole moment and the polarizability, as well as the frontier molecular orbitals and the charge distribution mapping, which impact the terminal and lateral interactions of the compounds. The theoretical results were discussed to confirm the experimental data and explain the mesomorphic behavior of the compounds. Finally, the energy gap, global softness, and chemical hardness were calculated to determine the suitability of the liquid crystalline compounds to be employed in applications.https://www.mdpi.com/2073-4352/12/7/902Schiff base liquid crystalsterminal pyridine liquid crystalstype and orientation mesogenic core effectDFT |
| spellingShingle | Jehan Y. Al-Humaidi Shady Nada Mariam Gerges Marwa Ehab Mariusz Jaremko Abdul-Hamid Emwas Mohamed Hagar 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation Crystals Schiff base liquid crystals terminal pyridine liquid crystals type and orientation mesogenic core effect DFT |
| title | 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation |
| title_full | 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation |
| title_fullStr | 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation |
| title_full_unstemmed | 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation |
| title_short | 2-Pyridinyl-Terminated Iminobenzoate: Type and Orientation of Mesogenic Core Effect, Geometrical DFT Investigation |
| title_sort | 2 pyridinyl terminated iminobenzoate type and orientation of mesogenic core effect geometrical dft investigation |
| topic | Schiff base liquid crystals terminal pyridine liquid crystals type and orientation mesogenic core effect DFT |
| url | https://www.mdpi.com/2073-4352/12/7/902 |
| work_keys_str_mv | AT jehanyalhumaidi 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT shadynada 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT mariamgerges 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT marwaehab 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT mariuszjaremko 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT abdulhamidemwas 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation AT mohamedhagar 2pyridinylterminatediminobenzoatetypeandorientationofmesogeniccoreeffectgeometricaldftinvestigation |