Synthesis, Properties and Dynamics of Near-IR BODIPY Fluorophores

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In this project funded by the Chemical Structure, Dynamic & Mechanism B Program of the Chemistry Division, Professor Maria da Graça H. Vicente of the Department of Chemistry at Louisiana State University, in collaboration with Associate Professor Petia Bobadova-Parvanova of the Department of Chemistry at Rockhurst University, will develop a new class of fluorescent dyes for use in biological applications, such as in bioimaging, biosensing, and bioanalyses. The goal of this research is to design, synthesize and then investigate the photophysical 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 the new fluorescent dyes and their conjugates, involving 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; reactions of the basic BODIPY core can be used for the tuning of the absorption and emission wavelengths, Stokes' shifts, photostability, quantum yields, water-solubility, and for introduction of functionality for conjugation. The proposed syntheses will afford pi-extended, beta, beta'-benzo-fuzed and 8-substituted BODIPYs. In this project, the main strategies are 1) to develop the use of benzo-annelation at the beta, beta'-pyrrolic positions of the BODIPY, as well as functionalizations of the 3,5-positions to increase the conjugated pi-system, rigidity, and water-solubility of the BODIPY core, 2) to investigate the introduction of a nitrogen atom at the 8-position via computational modeling and the synthesis of aza-BODIPYs, and 3) investigate the functionalization at the boron center via substitutions using various nucleophiles. 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 functionalizations of BODIPYs and aza-BODIPYs.