Janah Shaya
Université de Strasbourg, France
Title: Economic syntheses of push-pull fluorene probes using air-stable Pd catalytic systems: Applications into imaging of lipid membranes
Biography
Biography: Janah Shaya
Abstract
Extensive research continues to find catalytic methods and straightforward syntheses for biological and environmental applications. In particular, the architecture of new fluorescent tools is of huge demand. Push-pull dyes exhibiting the two-photon absorption (2PA) property are of particular interest. These dyes are highly responsive to changes of environment. They constitute useful biosensors and probes for specific detections of nucleic acids. They also enable imaging and penetration into cells with reduced photo-damage. Our work presents: 1) Step-economic and concise approaches to a spectrum of push-pull fluorene dyes: As an example, a planned route involved one-pot synthesis installing both the electron-donor and acceptor. Another route comprised selective formylation followed by C-N cross coupling via air-stable palladium catalytic systems, 2) Photo-physical characterization and structure-property relationships of a library of 20 synthesized fluorene compounds and 3) Application of an optimized solvatochromic fluorene probe to imaging lipid organization in cell membranes. The presented fluorene dye outperforms the features of popular probes like Laurdan. Some of the established improvements are: red-shifted absorption that matches the 405 nm diode laser, higher brightness decreasing the used concentration for such staining by 20 folds, remarkable photo-stability, compatibility with two-photon excitation at wavelength more than 800 nm, among others.
Figure-1: Graphical abstract.
Recent Publications
1. P M Holstein, D Dailler, J Vantourout, J Shaya, A Millet, O Baudoin (2016) Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)–H Alkenylation and Application to Alkaloid Synthesis. Angew. Chem. Int. Ed.; 55: 1–6.
2. J Shaya, F Fontaine-Vive, B Y Michel, A Burger (2016) Rational design of push-pull fluorene dyes: synthesis and structure-photophysics relationship. Chem. Eur. J.; 22: 10627-10637.
References:
1. J. Shaya, F. Fontaine-Vive, B. Y. Michel, A. Burger, “Rational design of push-pull fluorene dyes: synthesis and structure-photophysics relationship”, Chem. Eur. J. 2016, 22, 10627-10637.
2. J. Shaya, M. A. Deschamps, B. Y. Michel, A. Burger, “Air-stable palladium catalytic systems for sequential one-pot synthesis of challenging unsymmetrical aminated products”, J. Org. Chem. 2016, 81, 7566-7573.
3. J. Shaya, M. Collot, F. Bénailly, N. Mahmoud, Y. Mély, B. Y. Michel, A. S. Klymchenko, A. Burger, “Turn-On Fluorene Push-Pull Probes with High Brightness and Photostability for Visualizing the Different Liquid Domains of Cell Membranes”, ACS Chemical Biology, 2016, 12, 3022-3030.
4. S. Huang, C. Chen, H. Tsai, J. Shaya, C. Lu, “Photocatalytic degradation of thiobencarb by a visible light-driven MoS2 photocatalyst”, Separation and Purification Technology, 2018, 197, 147-155