Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold
A series of novel styrylquinolines with the benzylidene imine moiety were synthesized and spectroscopically characterized for their applicability in cellular staining. The spectroscopic study revealed absorption in the ultraviolet–visible region (360–380 nm) and emission that covered the blue-green...
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/11/2488 |
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| author | Barbara Czaplińska Katarzyna Malarz Anna Mrozek-Wilczkiewicz Aneta Slodek Mateusz Korzec Robert Musiol |
| author_facet | Barbara Czaplińska Katarzyna Malarz Anna Mrozek-Wilczkiewicz Aneta Slodek Mateusz Korzec Robert Musiol |
| author_sort | Barbara Czaplińska |
| collection | DOAJ |
| description | A series of novel styrylquinolines with the benzylidene imine moiety were synthesized and spectroscopically characterized for their applicability in cellular staining. The spectroscopic study revealed absorption in the ultraviolet–visible region (360–380 nm) and emission that covered the blue-green range of the light (above 500 nm). The fluorescence quantum yields were also determined, which amounted to 0.079 in the best-case scenario. The structural features that are behind these values are also discussed. An analysis of the spectroscopic properties and the theoretical calculations indicated the charge-transfer character of an emission, which was additionally evaluated using the Lippert–Mataga equation. Changes in geometry in the ground and excited states, which had a significant influence on the emission process, are also discussed. Additionally, the capability of the newly synthesized compounds for cellular staining was also investigated. These small molecules could effectively penetrate through the cellular membrane. Analyses of the images that were obtained with several of the tested styrylquinolines indicated their accumulation in organelles such as the mitochondria and the endoplasmic reticulum. |
| first_indexed | 2024-03-10T19:33:37Z |
| format | Article |
| id | doaj.art-53eb89672b6d4fe2b8fd15d19a4bc462 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:33:37Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-53eb89672b6d4fe2b8fd15d19a4bc4622023-11-20T01:56:19ZengMDPI AGMolecules1420-30492020-05-012511248810.3390/molecules25112488Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline ScaffoldBarbara Czaplińska0Katarzyna Malarz1Anna Mrozek-Wilczkiewicz2Aneta Slodek3Mateusz Korzec4Robert Musiol5Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pułku Piechoty 1A, 41-500 Chorzów, PolandA. Chełkowski Institute of Physics, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pułku Piechoty 1, 41-500 Chorzów, PolandA. Chełkowski Institute of Physics, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pułku Piechoty 1, 41-500 Chorzów, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, Szkolna 9, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, Szkolna 9, 40-007 Katowice, PolandInstitute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pułku Piechoty 1A, 41-500 Chorzów, PolandA series of novel styrylquinolines with the benzylidene imine moiety were synthesized and spectroscopically characterized for their applicability in cellular staining. The spectroscopic study revealed absorption in the ultraviolet–visible region (360–380 nm) and emission that covered the blue-green range of the light (above 500 nm). The fluorescence quantum yields were also determined, which amounted to 0.079 in the best-case scenario. The structural features that are behind these values are also discussed. An analysis of the spectroscopic properties and the theoretical calculations indicated the charge-transfer character of an emission, which was additionally evaluated using the Lippert–Mataga equation. Changes in geometry in the ground and excited states, which had a significant influence on the emission process, are also discussed. Additionally, the capability of the newly synthesized compounds for cellular staining was also investigated. These small molecules could effectively penetrate through the cellular membrane. Analyses of the images that were obtained with several of the tested styrylquinolines indicated their accumulation in organelles such as the mitochondria and the endoplasmic reticulum.https://www.mdpi.com/1420-3049/25/11/2488green fluorophoresquinolinelarge Stokes shiftintramolecular charge transfercell imagingDFT calculations |
| spellingShingle | Barbara Czaplińska Katarzyna Malarz Anna Mrozek-Wilczkiewicz Aneta Slodek Mateusz Korzec Robert Musiol Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold Molecules green fluorophores quinoline large Stokes shift intramolecular charge transfer cell imaging DFT calculations |
| title | Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold |
| title_full | Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold |
| title_fullStr | Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold |
| title_full_unstemmed | Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold |
| title_short | Theoretical and Experimental Investigations of Large Stokes Shift Fluorophores Based on a Quinoline Scaffold |
| title_sort | theoretical and experimental investigations of large stokes shift fluorophores based on a quinoline scaffold |
| topic | green fluorophores quinoline large Stokes shift intramolecular charge transfer cell imaging DFT calculations |
| url | https://www.mdpi.com/1420-3049/25/11/2488 |
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