9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications
Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized...
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| Format: | Article |
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MDPI AG
2017-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/12/2148 |
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| author | Mengjie Liu Sawaros Onchaiya Lewis Yi Fong Tan Mohammad A. Haghighatbin Tracey Luu Tze Cin Owyong Roozbeh Hushiarian Conor F. Hogan Trevor A. Smith Yuning Hong |
| author_facet | Mengjie Liu Sawaros Onchaiya Lewis Yi Fong Tan Mohammad A. Haghighatbin Tracey Luu Tze Cin Owyong Roozbeh Hushiarian Conor F. Hogan Trevor A. Smith Yuning Hong |
| author_sort | Mengjie Liu |
| collection | DOAJ |
| description | Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using fluorometric analyses, these dyes were confirmed to show AIE behavior upon forming aggregates at high concentrations, in viscous solvents, and when poorly solubilized. Their photophysical properties were then further correlated with their structural features, using density functional theory (DFT) calculation. Finally, we demonstrated their potential applications in monitoring pH changes, quantifying globular proteins, as well as cell imaging with confocal microscopy. |
| first_indexed | 2024-04-13T10:53:44Z |
| format | Article |
| id | doaj.art-c8e29e8c22024654a6725912d0c0a188 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T10:53:44Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c8e29e8c22024654a6725912d0c0a1882022-12-22T02:49:34ZengMDPI AGMolecules1420-30492017-12-012212214810.3390/molecules22122148molecules221221489-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and ApplicationsMengjie Liu0Sawaros Onchaiya1Lewis Yi Fong Tan2Mohammad A. Haghighatbin3Tracey Luu4Tze Cin Owyong5Roozbeh Hushiarian6Conor F. Hogan7Trevor A. Smith8Yuning Hong9Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaSchool of Chemistry, The University of Melbourne, Parkville, VIC 3010, AustraliaDepartment of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, AustraliaFluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using fluorometric analyses, these dyes were confirmed to show AIE behavior upon forming aggregates at high concentrations, in viscous solvents, and when poorly solubilized. Their photophysical properties were then further correlated with their structural features, using density functional theory (DFT) calculation. Finally, we demonstrated their potential applications in monitoring pH changes, quantifying globular proteins, as well as cell imaging with confocal microscopy.https://www.mdpi.com/1420-3049/22/12/2148aggregation-induced emissionanthracenesolvatochromism |
| spellingShingle | Mengjie Liu Sawaros Onchaiya Lewis Yi Fong Tan Mohammad A. Haghighatbin Tracey Luu Tze Cin Owyong Roozbeh Hushiarian Conor F. Hogan Trevor A. Smith Yuning Hong 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications Molecules aggregation-induced emission anthracene solvatochromism |
| title | 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications |
| title_full | 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications |
| title_fullStr | 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications |
| title_full_unstemmed | 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications |
| title_short | 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications |
| title_sort | 9 vinylanthracene based fluorogens synthesis structure property relationships and applications |
| topic | aggregation-induced emission anthracene solvatochromism |
| url | https://www.mdpi.com/1420-3049/22/12/2148 |
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