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Molecules 2017, 22(12), 2148; doi:10.3390/molecules22122148

9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications

1
Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
2
School of Chemistry, The University of Melbourne, Parkville, VIC 3010, Australia
These authors contributed equally to this work.
Current address: Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
*
Author to whom correspondence should be addressed.
Received: 1 September 2017 / Revised: 24 November 2017 / Accepted: 1 December 2017 / Published: 4 December 2017
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Abstract

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. View Full-Text
Keywords: aggregation-induced emission; anthracene; solvatochromism aggregation-induced emission; anthracene; solvatochromism
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Liu, M.; Onchaiya, S.; Tan, L.Y.F.; Haghighatbin, M.A.; Luu, T.; Owyong, T.C.; Hushiarian, R.; Hogan, C.F.; Smith, T.A.; Hong, Y. 9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications. Molecules 2017, 22, 2148.

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