Synthesis, Properties and Dynamics of Near-IR BODIPY Fluorophores

近红外 BODIPY 荧光团的合成、性质和动力学

• 批准号: 1362641
• 负责人: Maria Vicente
• 金额: $ 39万
• 依托单位: Louisiana State University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2014
• 资助国家: 美国
• 起止时间: 2014-08-01 至 2018-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1362641&HistoricalAwards=false
• 关键词: Synthesis; Properties; Dynamics; Near; IR

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.

在化学系化学结构、动力学机制B项目资助的这一项目中，Maria da Graça H.路易斯安那州立大学化学系的Vicente与罗克赫斯特大学化学系的Petia Bobadova-Parvanova副教授合作，将开发一类新的荧光染料用于生物应用，如生物成像，生物传感和生物分析。 本研究的目标是设计，合成，然后研究新染料的生物物理和细胞特性，以开发可与蛋白质和其他生物分子缀合的近红外吸收和发射荧光团。 该项目涉及计算和实验方法来设计，合成和评估新的荧光染料及其共轭物，涉及有机和无机化学，光谱学，化学动力学，计算建模，细胞和分子生物学，分子识别和生物医学成像，因此非常适合各级科学家的教育。 该小组也有能力为科学领域代表性不足的学生提供最高水平的教育和培训。 涉及K-12学生的外联活动也将是资助项目的一部分。 硼二吡咯亚甲基（BODIPY）染料具有丰富的物理和光电性质，包括强的吸收和发射光谱、高的摩尔消光系数、高的荧光量子产率和长的荧光寿命;基本BODIPY核的反应可用于调节吸收和发射波长、斯托克斯位移、光稳定性、量子产率、水溶性以及引入用于共轭的官能团。所提出的合成将提供π-延伸的、β，β ′-苯并-稠合的和8-取代的BODIPY。 在这个项目中，主要策略是1）开发在BODIPY的β，β '-吡咯位置处的苯并-annealing的用途，以及3，5-位置的官能化，以增加BODIPY核心的共轭π-系统、刚性和水溶性，2）通过计算建模和氮杂-BODIPY的合成来研究在8-位置处引入氮原子，和3）研究通过使用各种亲核试剂的取代在硼中心处的官能化。该项目利用计算方法来辅助目标设计和建模BODIPY机制和性质，并探索BODIPY和aza-BODIPY合成和功能化的新方法。