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

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

doi:10.3390/molecules22122148

Molecules (Dec 2017)

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

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

Affiliations

Mengjie Liu: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Sawaros Onchaiya: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Lewis Yi Fong Tan: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Mohammad A. Haghighatbin: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Tracey Luu: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Tze Cin Owyong: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Roozbeh Hushiarian: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Conor F. Hogan: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Trevor A. Smith: School of Chemistry, The University of Melbourne, Parkville, VIC 3010, Australia
Yuning Hong: Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia

DOI: https://doi.org/10.3390/molecules22122148
Journal volume & issue: Vol. 22, no. 12
p. 2148

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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