First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications
New liquid crystalline hydrogen bonded 3- (or 4)-n-alkanoyloxy benzoic acids were synthesized and probed theoretically and experimentally. The molecular structures of these compounds were elucidated by proton NMR, carbon-13 NMR and elemental analyses. Differential scanning calorimetry (DSC) was used...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-09-01
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| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844023065921 |
| _version_ | 1797669914241138688 |
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| author | Mohamed A. El-Atawy Mohd Taukeer Khan Saheed A. Popoola Muna S. Khushaim Mariusz Jaremko Abdul-Hamid Emwas Fowzia S. Alamro Magdi M. Naoum Hoda A. Ahmed |
| author_facet | Mohamed A. El-Atawy Mohd Taukeer Khan Saheed A. Popoola Muna S. Khushaim Mariusz Jaremko Abdul-Hamid Emwas Fowzia S. Alamro Magdi M. Naoum Hoda A. Ahmed |
| author_sort | Mohamed A. El-Atawy |
| collection | DOAJ |
| description | New liquid crystalline hydrogen bonded 3- (or 4)-n-alkanoyloxy benzoic acids were synthesized and probed theoretically and experimentally. The molecular structures of these compounds were elucidated by proton NMR, carbon-13 NMR and elemental analyses. Differential scanning calorimetry (DSC) was used to investigate the thermal and mesomorphic properties of all the symmetrical dimers that bearing identical alkanoyloxy chains. Moreover, polarized optical microscopy (POM) was used to determine their mesophases. The findings show that all the designed symmetrical dimers exhibit the smectic mesophase with relative thermal stability that depends on the length of their terminal side chain. Additionally, the experimental findings of the mesomorphic behavior are further supported by DFT calculations. The alkanoyloxy benzoic acid para-derivatives (In) were shown to be more stable than their meta-substituted (IIn) analogues due to stronger hydrogen bonding interactions. The computed reactivity parameters showed that the position of ester moiety has a significant impact on the acids reactivity. The absorbance spectra of both the 3- (or 4)-n-alkanoyloxy benzoic acids revealed a blue shift with the increment of the of alkyl chain size; however, the energy band gaps of 3-n-alkanoyloxy benzoic derivatives were found to be slightly higher than those of the 4-n-alkanoyloxy benzoic acids. Moreover, the photoluminescence spectrum of the prepared materials is rather broad, and exhibited a red shift as the alkyl chain length increases. The fluorescence lifetime shown to rise as alkyl chain length grows longer, and 3-n-alkanoyloxy benzoic acids have slightly longer lifetime compared to their 4-n-alkanoyloxy benzoic analogues. |
| first_indexed | 2024-03-11T20:51:47Z |
| format | Article |
| id | doaj.art-8d78a094d3924717be0083d1b383b113 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-11T20:51:47Z |
| publishDate | 2023-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-8d78a094d3924717be0083d1b383b1132023-10-01T05:59:25ZengElsevierHeliyon2405-84402023-09-0199e19384First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applicationsMohamed A. El-Atawy0Mohd Taukeer Khan1Saheed A. Popoola2Muna S. Khushaim3Mariusz Jaremko4Abdul-Hamid Emwas5Fowzia S. Alamro6Magdi M. Naoum7Hoda A. Ahmed8Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahemia, Alexandria 21321, Egypt; Chemistry Department, College of Sciences, Taibah University, Yanbu 30799, Saudi ArabiaDepartment of Physics, Faculty of Science, Islamic University of Madinah, Al-Madinah Al-Munawwarah 42351, Saudi ArabiaChemistry Department, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi ArabiaDepartment of Physics, Faculty of Science, Taibah University, P.O. Box 30002, Al-Madina 41447, Saudi Arabia; Strategic Research Labs, Taibah University, P.O. Box 30002, Al-Madina 41447, Saudi ArabiaBiological and Environmental Sciences & Engineering Division (BESE), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi ArabiaCore Labs., King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi ArabiaDepartment of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Cairo University, Giza 12613, EgyptDepartment of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt; Corresponding author.New liquid crystalline hydrogen bonded 3- (or 4)-n-alkanoyloxy benzoic acids were synthesized and probed theoretically and experimentally. The molecular structures of these compounds were elucidated by proton NMR, carbon-13 NMR and elemental analyses. Differential scanning calorimetry (DSC) was used to investigate the thermal and mesomorphic properties of all the symmetrical dimers that bearing identical alkanoyloxy chains. Moreover, polarized optical microscopy (POM) was used to determine their mesophases. The findings show that all the designed symmetrical dimers exhibit the smectic mesophase with relative thermal stability that depends on the length of their terminal side chain. Additionally, the experimental findings of the mesomorphic behavior are further supported by DFT calculations. The alkanoyloxy benzoic acid para-derivatives (In) were shown to be more stable than their meta-substituted (IIn) analogues due to stronger hydrogen bonding interactions. The computed reactivity parameters showed that the position of ester moiety has a significant impact on the acids reactivity. The absorbance spectra of both the 3- (or 4)-n-alkanoyloxy benzoic acids revealed a blue shift with the increment of the of alkyl chain size; however, the energy band gaps of 3-n-alkanoyloxy benzoic derivatives were found to be slightly higher than those of the 4-n-alkanoyloxy benzoic acids. Moreover, the photoluminescence spectrum of the prepared materials is rather broad, and exhibited a red shift as the alkyl chain length increases. The fluorescence lifetime shown to rise as alkyl chain length grows longer, and 3-n-alkanoyloxy benzoic acids have slightly longer lifetime compared to their 4-n-alkanoyloxy benzoic analogues.http://www.sciencedirect.com/science/article/pii/S24058440230659213- (or 4-)-n-alkanoyloxy benzoic acidsSymmetrical supramolecular-H bondingSmectic phaseCharacterizationsMesophase stabilityDFT |
| spellingShingle | Mohamed A. El-Atawy Mohd Taukeer Khan Saheed A. Popoola Muna S. Khushaim Mariusz Jaremko Abdul-Hamid Emwas Fowzia S. Alamro Magdi M. Naoum Hoda A. Ahmed First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications Heliyon 3- (or 4-)-n-alkanoyloxy benzoic acids Symmetrical supramolecular-H bonding Smectic phase Characterizations Mesophase stability DFT |
| title | First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications |
| title_full | First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications |
| title_fullStr | First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications |
| title_full_unstemmed | First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications |
| title_short | First mesomorphic and DFT characterizations for 3- (or 4-) n-alkanoyloxy benzoic acids and their optical applications |
| title_sort | first mesomorphic and dft characterizations for 3 or 4 n alkanoyloxy benzoic acids and their optical applications |
| topic | 3- (or 4-)-n-alkanoyloxy benzoic acids Symmetrical supramolecular-H bonding Smectic phase Characterizations Mesophase stability DFT |
| url | http://www.sciencedirect.com/science/article/pii/S2405844023065921 |
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