Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator
Aromatic nucleophilic substitution (SNAr) reactions have been known to be regioselective to the para position on a variety of substituted perfluorobenzenes. In the current study, a series of fluoroaryl 1, 3, 4-oxadiazole derivatives substituted with different para terminal ethers were synthesized us...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2022-05-01
|
| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535222000879 |
| _version_ | 1811290563262021632 |
|---|---|
| author | Aisha Hossan Hana M. Abumelha Rua B. Alnoman Abrar Bayazeed Amerah Alsoliemy Ali A. Keshk Nashwa M. El-Metwaly |
| author_facet | Aisha Hossan Hana M. Abumelha Rua B. Alnoman Abrar Bayazeed Amerah Alsoliemy Ali A. Keshk Nashwa M. El-Metwaly |
| author_sort | Aisha Hossan |
| collection | DOAJ |
| description | Aromatic nucleophilic substitution (SNAr) reactions have been known to be regioselective to the para position on a variety of substituted perfluorobenzenes. In the current study, a series of fluoroaryl 1, 3, 4-oxadiazole derivatives substituted with different para terminal ethers were synthesized using SNAr chemistry to afford fluorescent and thermally reversible low molecular weight organogelators (LMWOs). SNAr was used to synthesize these highly fluorinated organogelators in high purity and good yields starting from pentafluorobenzoic acid and 4′-hydroxy-4-biphenylcarbonitrile. These fluorinated 1, 3, 4-oxadiazole derivatives were characterized by elemental analysis, FTIR, and 1H, 13C, and 19F NMR spectroscopy. The photophysical properties of those organogelators were described. Both UV–visible absorption and fluorescence spectral profiles displayed a solvatochromic and solvatofluorochromic properties. The absorption maxima for the developed organogelators were monitored in the range of 260–289 nm, whereas the emission maxima were monitored in the range of 278–305 nm. The best gelation properties were monitored for the hexyloxy-substituted 2-(biphenylyl)-5-(perflurophenyl)-1, 3, 4-oxadiazole gelator in different solvents with critical gel concentrations in the range of 1.86–5.07 mM. The self-assembly process was monitored to occur via van der Waals forces and π-π stacks to result in gelation of solvents. Scanning electron microscope (SEM) demonstrated nanofiber-like structures (350–550 nm). The thermal stability of the hexyloxy-substituted organogel was monitored at 48 °C. Both cytotoxicity and antimicrobial activity of the produced fluoroaryl 1, 3, 4-oxadiazole derivatives were explored to verify their potential use for biomedical applications, such as drug delivery and bioimaging. |
| first_indexed | 2024-04-13T04:14:53Z |
| format | Article |
| id | doaj.art-e4e3195b59334794b2026a985982be4f |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-13T04:14:53Z |
| publishDate | 2022-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-e4e3195b59334794b2026a985982be4f2022-12-22T03:03:01ZengElsevierArabian Journal of Chemistry1878-53522022-05-01155103771Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelatorAisha Hossan0Hana M. Abumelha1Rua B. Alnoman2Abrar Bayazeed3Amerah Alsoliemy4Ali A. Keshk5Nashwa M. El-Metwaly6Chemistry Department, Faculty of Science, King Khalid University, Abha, Saudi ArabiafDepartment of Chemistry ,College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, College of Science, Taibah University, Madinah, P.O. Box 344, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm-Al-Qura University, Makkah 24230, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm-Al-Qura University, Makkah 24230, Saudi ArabiaDepertment of Chemistry, Faculty of Science, Tabuk University, Tabuk-71491, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm-Al-Qura University, Makkah 24230, Saudi Arabia; Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street 35516, Egypt; Corresponding author.Aromatic nucleophilic substitution (SNAr) reactions have been known to be regioselective to the para position on a variety of substituted perfluorobenzenes. In the current study, a series of fluoroaryl 1, 3, 4-oxadiazole derivatives substituted with different para terminal ethers were synthesized using SNAr chemistry to afford fluorescent and thermally reversible low molecular weight organogelators (LMWOs). SNAr was used to synthesize these highly fluorinated organogelators in high purity and good yields starting from pentafluorobenzoic acid and 4′-hydroxy-4-biphenylcarbonitrile. These fluorinated 1, 3, 4-oxadiazole derivatives were characterized by elemental analysis, FTIR, and 1H, 13C, and 19F NMR spectroscopy. The photophysical properties of those organogelators were described. Both UV–visible absorption and fluorescence spectral profiles displayed a solvatochromic and solvatofluorochromic properties. The absorption maxima for the developed organogelators were monitored in the range of 260–289 nm, whereas the emission maxima were monitored in the range of 278–305 nm. The best gelation properties were monitored for the hexyloxy-substituted 2-(biphenylyl)-5-(perflurophenyl)-1, 3, 4-oxadiazole gelator in different solvents with critical gel concentrations in the range of 1.86–5.07 mM. The self-assembly process was monitored to occur via van der Waals forces and π-π stacks to result in gelation of solvents. Scanning electron microscope (SEM) demonstrated nanofiber-like structures (350–550 nm). The thermal stability of the hexyloxy-substituted organogel was monitored at 48 °C. Both cytotoxicity and antimicrobial activity of the produced fluoroaryl 1, 3, 4-oxadiazole derivatives were explored to verify their potential use for biomedical applications, such as drug delivery and bioimaging.http://www.sciencedirect.com/science/article/pii/S1878535222000879Aromatic nucleophilic substitutionDecarboxylation cross-coupling1, 3, 4-OxadiazoleFluorescenceOrganogelator |
| spellingShingle | Aisha Hossan Hana M. Abumelha Rua B. Alnoman Abrar Bayazeed Amerah Alsoliemy Ali A. Keshk Nashwa M. El-Metwaly Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator Arabian Journal of Chemistry Aromatic nucleophilic substitution Decarboxylation cross-coupling 1, 3, 4-Oxadiazole Fluorescence Organogelator |
| title | Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator |
| title_full | Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator |
| title_fullStr | Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator |
| title_full_unstemmed | Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator |
| title_short | Synthesis, self-assembly and optical properties of novel fluorescent alkoxy-substituted fluoroaryl 1, 3, 4-oxadiazole organogelator |
| title_sort | synthesis self assembly and optical properties of novel fluorescent alkoxy substituted fluoroaryl 1 3 4 oxadiazole organogelator |
| topic | Aromatic nucleophilic substitution Decarboxylation cross-coupling 1, 3, 4-Oxadiazole Fluorescence Organogelator |
| url | http://www.sciencedirect.com/science/article/pii/S1878535222000879 |
| work_keys_str_mv | AT aishahossan synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT hanamabumelha synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT ruabalnoman synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT abrarbayazeed synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT amerahalsoliemy synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT aliakeshk synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator AT nashwamelmetwaly synthesisselfassemblyandopticalpropertiesofnovelfluorescentalkoxysubstitutedfluoroaryl134oxadiazoleorganogelator |