Synthesis, Properties and Dynamics of BODIPY-based Fluorophores

In this project, funded by the Chemical Structure, Dynamics and Mechanism-B program of the NSF Chemistry Division, Professor Maria da Graça H. Vicente of the Department of Chemistry at Louisiana State University, in collaboration with Professor Petia Bobadova of the Department of Chemistry and Fermentation Sciences at Appalachian State University, will develop new fluorescent dyes for use in biology and materials science.

The main goals are to design and synthesize new fluorinated boron dipyrromethene (BODIPY) dyes and their derivatives, followed by investigation of their photophysical and chemical properties, and their potential applications. This research is directed toward the development of near-infrared absorbing and emitting fluorophores that can find applications in sensing and/or be conjugated with biomolecules for bioimaging applications.

Computational and experimental methods will be used to design, synthesize and evaluate new fluorescent dyes and their conjugates, seeking enhanced stability, biocompatibility and performance for practical applications. This project encompasses organic and inorganic chemistry, spectroscopy, chemical kinetics, computational modeling, cell and molecular biology, molecular recognition, and biomedical imaging, and is therefore well suited to the education of scientists at all levels.

This group is also well-positioned to provide the highest level of education and training for students at all levels, including those underrepresented in science. Dr. Vicente leads programs at LSU that will enhance student learning and professional skills, enrich their educational experiences, and encourage them to pursue research careers.

Outreach activities involving K-12 students will also be part of the funded project, both at LSU and at Appalachian State University.

Boron dipyrromethene (BODIPY) dyes display a rich array of photophysical and optoelectronic properties, including intense absorption and emission profiles, high molar extinction coefficients, high fluorescence quantum yields and long fluorescence lifetimes. Chemical modifications of the BODIPY core can be used to tune the absorption and emission wavelengths, Stokes shifts, stability, quantum yields, water-solubility, and to introduce functionality suitable for conjugation to biomolecules.

This project aims to provide new BODIPY-based systems with enhanced stability, solubility, and photophysical properties for practical applications in bioimaging and biosensing, including bis-boron derivatives designated as BOPHY, BOPYPY, BOPYPY and BOAPY. The main strategies are: 1) Regioselective functionalization to create push-pull BODIPY systems and dyads with enhanced molar extinction coefficients, fluorescence emission and Stokes shifts, increased oxidative stability and solubility. 2) Synthesis and investigation of unsymmetric BODIPY-based fluorophores bearing two electron-deficient boron centers and their investigation as solid-state emissive organic materials. 3) Use of poly-fluorination for enhancement of cellular permeability, stability, and biocompatibility, and to allow sites for conjugation with bio-thiols.

Computational methods will be used to assist the target design by modeling BODIPY properties and mechanisms, thus facilitating the development of new methodologies for the synthesis and functionalization of BODIPY-based systems. This project encompasses a broad range of science and techniques, which will provide the highest level of education and training for students at all levels underrepresented in science.

This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.