新型α,β位稠环Aza-BODIPY近红外染料的合成及性能研究

Near-infared dyes have important applications in the areas of biomedical and material science. In recent years, Aza-BODIPY has been attracted high attention due to their excellent photochemical and photophysical properties, such as long excitation wavelength and good photostability. In this project, we will synthesize a series of novel near-infared α,β aromatic ring-fused Aza-BODIPY dyes by explioting C-C coupling and C-N coupling on Aza-BODIPY core and then cyclizing by oxidative coupling using FeCl3, study their spectral properties, photostabilities, electrochemical properties and potential applications in cell imaging, and analyze the influence from the position of substituents, sterical hendrance and electron distribution and water solubility on properties of these novel near-infared dyes. Based on this, the project will optimize the target molecules and expliot a novel efficiently synthetic method for longer Aza-BODIPY dyes and develop a new type of these dyes, featured with good water-solubility and good stabilities. The project will produce a good reference for designing and synthsizing longer near-infared dyes, especially for near-infared Aza-BODIPY dyes.

近红外染料在生物医学和材料科学等领域具有重要的应用。近年来Aza-BODIPY由于具有长波激发、稳定性高等优异性能备受关注。本课题拟通过在Aza-BODIPY骨架上发展C-C、C-N耦联反应继而用FeCl3氧化耦联环化，合成一类新型α,β位芳环稠合修饰的Aza-BODIPY近红外染料；研究所合成染料的光谱性质、光稳定性、电化学性质及其在细胞成像的应用，并分析比较取代基的位置、位阻、电子效应以及水溶性对于上述性能的影响。在此基础上，进一步优化目标分子。以期开发一种构建该类近红外染料的高效合成方法，发展一类具良好溶解性和稳定性的更长波Aza-BODIPY近红外染料分子。该课题的成功实施将为进一步有效设计新型近红外染料分子（尤其是更长波近红外Aza-BODIPY染料）提供参考。

近红外染料分子在生物医学和材料科学等领域具有重要应用，例如已广泛应用在非侵入性活体荧光成像、荧光标记以及生物传感等领域。目前限制其进一步应用的主要因素来自有限的近红外染料种类，尤其是具有良好光谱选择性和稳定性的近红外染料分子。本项目研究了一系列α,β芳环稠合修饰的Aza-BODIPY近红外染料，发展了利用无水三氯化铁实现的分子内氧化关环反应或钯催化的C-H活化构建这些α,β芳环稠合Aza-BODIPY染料骨架的高效方法。我们接着研究了这些染料的光谱性能、光化学稳定性、电化学性能及在细胞成像中的应用光学性能；我们还合成了系列氟硼吡咯染料及其类似物并通过化学修饰调控其光谱性能；这些新型近红外染料分子和我们所发展的该些合成方法将有望进一步推动新型近红外染料在生物医学和材料科学等领域的应用。