Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor)
Structurally interesting chromeno-quinolines were constructed via the cyclization reaction of O-propargylated naphthaldehyde and substituted anilines in good yields. We explored compound methyl-chromenoquinoline (MCQ) in detail for its optical properties using Time-dependent density-functional theor...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-10-01
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| Series: | Journal of King Saud University: Science |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1018364722004414 |
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| author | Saradh Prasad Mohamad S. Alsalhi Raju Suresh Kumar Abdulrahman I. Almansour Natarajan Arumugam Manal Fahad Alkaltham Khloud Ibrahim Al-Shemaimari Haya bint Abdulaziz Al-Tamimi |
| author_facet | Saradh Prasad Mohamad S. Alsalhi Raju Suresh Kumar Abdulrahman I. Almansour Natarajan Arumugam Manal Fahad Alkaltham Khloud Ibrahim Al-Shemaimari Haya bint Abdulaziz Al-Tamimi |
| author_sort | Saradh Prasad |
| collection | DOAJ |
| description | Structurally interesting chromeno-quinolines were constructed via the cyclization reaction of O-propargylated naphthaldehyde and substituted anilines in good yields. We explored compound methyl-chromenoquinoline (MCQ) in detail for its optical properties using Time-dependent density-functional theory (TD-DFT) and experimental studies. The conjugated-polymer (CP) Poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(2,5-p-xylene)] or [(ADS145UV or PFOPX)] was studied as donor. The TD-DFT implied that MCQ is a fluorescent compound with well-defined highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) structure at −5.327 eV and −1.836 eV, respectively, with an energy gap of 3.49 eV in toluene captivity. The TD-DFT-based model and experimental study showed an energy gap of 3.326 eV and 3.351 eV, respectively, and the deviation was 0.025 eV. The experimental studies of MCQ showed solvent-dependent fluorescence peak shifted from 445 ± 2 nm to 538 ± 2 nm for dielectric constant ranging from 0.01 (hexane) to 10.2 (water). Despite the good optical properties, MCQ produced a weak laser-induced fluorescence (LIF) and not produce amplified spontaneous emission (ASE) to any pump energy of 3rd harmonic from Nd:YAG laser (5 ns, 355 nm). When PFOPX of concentration 500 nM (500 μL) was added to MCQ of 506 mM (3.5 mL) concentration, the LIF suddenly improved tenfold due to efficient Fluorescence resonance energy transfer (FRET) process. At the optimal concentration of PFOPX (670 nM) in MCQ solution, the spectrum changed dramatically. The spectrum has five peaks with a LIF in the background, where peaks around 393.5 nm and 417.3 nm attribute to the oligomer; 438.7 nm attributed to a combined fluorescence of PFOPX and MCQ; 466.4 nm, and 493.1 nm corresponding to MCQ. Analysis shows that the peaks at 440 nm (partly) and 493 nm were ASE from MCQ. |
| first_indexed | 2024-04-11T21:12:59Z |
| format | Article |
| id | doaj.art-63db94b6b5f44c6bb24124b189a35787 |
| institution | Directory Open Access Journal |
| issn | 1018-3647 |
| language | English |
| last_indexed | 2024-04-11T21:12:59Z |
| publishDate | 2022-10-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of King Saud University: Science |
| spelling | doaj.art-63db94b6b5f44c6bb24124b189a357872022-12-22T04:02:58ZengElsevierJournal of King Saud University: Science1018-36472022-10-01347102260Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor)Saradh Prasad0Mohamad S. Alsalhi1Raju Suresh Kumar2Abdulrahman I. Almansour3Natarajan Arumugam4Manal Fahad Alkaltham5Khloud Ibrahim Al-Shemaimari6Haya bint Abdulaziz Al-Tamimi7Department of Physics and Astronomy, College of Science, King Saud University, 11451 Riyadh, Saudi Arabia; Research Chair on Laser Diagnosis of Cancers, Department of Physics and Astronomy, College of Science, King Saud University, 11451 Riyadh, Saudi ArabiaDepartment of Physics and Astronomy, College of Science, King Saud University, 11451 Riyadh, Saudi Arabia; Research Chair on Laser Diagnosis of Cancers, Department of Physics and Astronomy, College of Science, King Saud University, 11451 Riyadh, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi Arabia; Corresponding author.Department of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Physics and Astronomy, College of Science, King Saud University, 11451 Riyadh, Saudi ArabiaStructurally interesting chromeno-quinolines were constructed via the cyclization reaction of O-propargylated naphthaldehyde and substituted anilines in good yields. We explored compound methyl-chromenoquinoline (MCQ) in detail for its optical properties using Time-dependent density-functional theory (TD-DFT) and experimental studies. The conjugated-polymer (CP) Poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(2,5-p-xylene)] or [(ADS145UV or PFOPX)] was studied as donor. The TD-DFT implied that MCQ is a fluorescent compound with well-defined highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) structure at −5.327 eV and −1.836 eV, respectively, with an energy gap of 3.49 eV in toluene captivity. The TD-DFT-based model and experimental study showed an energy gap of 3.326 eV and 3.351 eV, respectively, and the deviation was 0.025 eV. The experimental studies of MCQ showed solvent-dependent fluorescence peak shifted from 445 ± 2 nm to 538 ± 2 nm for dielectric constant ranging from 0.01 (hexane) to 10.2 (water). Despite the good optical properties, MCQ produced a weak laser-induced fluorescence (LIF) and not produce amplified spontaneous emission (ASE) to any pump energy of 3rd harmonic from Nd:YAG laser (5 ns, 355 nm). When PFOPX of concentration 500 nM (500 μL) was added to MCQ of 506 mM (3.5 mL) concentration, the LIF suddenly improved tenfold due to efficient Fluorescence resonance energy transfer (FRET) process. At the optimal concentration of PFOPX (670 nM) in MCQ solution, the spectrum changed dramatically. The spectrum has five peaks with a LIF in the background, where peaks around 393.5 nm and 417.3 nm attribute to the oligomer; 438.7 nm attributed to a combined fluorescence of PFOPX and MCQ; 466.4 nm, and 493.1 nm corresponding to MCQ. Analysis shows that the peaks at 440 nm (partly) and 493 nm were ASE from MCQ.http://www.sciencedirect.com/science/article/pii/S1018364722004414ChromenoquinolinesMCQPFOPXEnergy transferFRETASE |
| spellingShingle | Saradh Prasad Mohamad S. Alsalhi Raju Suresh Kumar Abdulrahman I. Almansour Natarajan Arumugam Manal Fahad Alkaltham Khloud Ibrahim Al-Shemaimari Haya bint Abdulaziz Al-Tamimi Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) Journal of King Saud University: Science Chromenoquinolines MCQ PFOPX Energy transfer FRET ASE |
| title | Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) |
| title_full | Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) |
| title_fullStr | Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) |
| title_full_unstemmed | Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) |
| title_short | Synthesis, TD-DFT, and optical properties study of a chromeno-quinoline (acceptor) and mirror-less laser action enabled by energy transfer from a conjugated-polymer (Donor) |
| title_sort | synthesis td dft and optical properties study of a chromeno quinoline acceptor and mirror less laser action enabled by energy transfer from a conjugated polymer donor |
| topic | Chromenoquinolines MCQ PFOPX Energy transfer FRET ASE |
| url | http://www.sciencedirect.com/science/article/pii/S1018364722004414 |
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