Synthesis, Properties and Dynamics of BODIPY-based Fluorophores

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In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor Maria G Vicente of the Department of Chemistry at Louisiana State University, in collaboration with Professor Petia N Bobadova-Parvanova of the Department of Chemistry at Rockhurst University, are developing fluorescent dyes for use in biological and material applications, including in bioimaging, and chemosensing. The goal of this research is to design, synthesize and then investigate the photophysical, electrochemical, and cellular properties of the new dyes toward the development of near-infrared absorbing and emitting fluorophores that can be conjugated with proteins and other biomolecules. The project involves both computational and experimental methods to design, synthesize and evaluate new fluorescent dyes and their conjugates, of enhanced stability, biocompatibility and performance for practical applications. This project involves 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 underrepresented in science. Outreach activities involving K-12 students will also be part of the funded project. 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. Previous work demonstrated that reactions of the basic BODIPY core can be used for the tuning of the absorption and emission wavelengths, Stokes shifts, stability, quantum yields, water-solubility, and for introduction of functionality for conjugation. The proposed syntheses will afford BODIPY-based systems with enhanced stability, solubility, and photophysical properties for practical applications in bioimaging and biosensing. In this project, the main strategies are 1) use of benzo-annelation via efficient intramolecular cyclizations to produce fused BODIPY systems with enhanced rigidity, and near-IR absorptions/emissions, 2) regioselective functionalizations to create push-pull BODIPY systems and BODIPY dyads with enhanced molar extinction coefficients, fluorescence emissions, Stokes shifts, as well as with increased oxidation potentials and solubility, and 3) use of polyfluorination for enhancement of cellular permeability, stability, and biocompatibility. The project takes advantage of computational methods to assist the target design and to model BODIPY mechanisms and properties, and explores new methodologies for the synthesis and functionalization of BODIPYs.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.