9-vinylanthracene based fluorogens: Synthesis, structure-property relationships and applications

• Main Authors: 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
• Other Authors: La Trobe University
• Format: Article
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/41730
• Institution: Mahidol University

© 2017 by the authors. 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.