【作者】 王佳；

【导师】 高保祥；

【作者基本信息】 河北大学 ， 高分子化学与物理， 2015， 硕士

【摘要】 苝酰亚胺是一类光、热、化学稳定性优异,具有高的吸光系数和荧光量子产率的有机发光染料,在有机光电材料、生物标记和单分子光谱学等领域具有重要应用价值。氟原子具有强的电负性和较小的原子半径,其结构上的这些特点,赋予了氟修饰化合物许多优良的性质:热、化学稳定性和生物相容性。因此,含氟化合物的研究受到人们广泛的关注。本论文主要研究了氟原子的引入,对苝酰亚胺光电性质的影响以及氟化苝类探针在活细胞荧光成像中的应用。具体工作如下:1、在苝酰亚胺的海湾部位分别引入氟取代基和苯取代基,合成了FPDI-1、FPDI-2和PPDI,对其光电性质进行了表征。三种化合物在氯仿溶液中均具有较高的荧光量子产率(59%-63%)和良好的光稳定性。随着氟原子的引入,FPDI-1和FPDI-2的最大吸收和发射波长均出现蓝移。随着引入氟原子个数的增多,PPDI、FPDI-1和FPDI-2的最低未占据轨道(LUMO)能级逐渐降低,由-3.82e V降低至-3.96e V。同时,其最高占据轨道(HOMO)能级,随着氟原子个数的增多,也呈现出逐渐降低的趋势,由-5.89e V降低至-6.12e V。2、在苝酰亚胺N位置上引入亲水性的支化PEG结构单元,合成了一类具有良好水溶性的苝类探针BPPDI、BFPDI-1和BFPDI-2,对其光电性质和活细胞荧光成像进行了研究。随着海湾部位氟原子个数的增多,三种探针在水溶液中的荧光量子产率逐渐提高,由15%升高至36%。三种化合物均具有良好的水溶性、生物相容性和pH稳定性。随着氟原子个数的增多,其荧光图像的亮度和细胞内的荧光稳定性逐渐升高,其中BFPDI-2的活细胞荧光成像效果最佳。更多还原

【Abstract】 Perylene diimides(PDIs) represent a class of organic chromophores with photochemical stabilities, high extinction coefficients, and high quantum yields. PDIs are key chromophores for high-tech applications, such as organic optoelectronic devices, biolabeling, and single molecular spectroscopy. Electronegativity of fluorine atom is strong and atomic radius of it was small. Fluorinated compounds display a variety of excellent properties, such as thermal stability, chemical stability, and cytocompatibility. Therefore, the study of fluorinated compounds has attracted more and more attention. In this thesis, we mainly studied the electrochemical-photophysical properties of PDIs with fluorinated substituents on the bay, and applications for cellular imaging. The main contents are as follows.1. Fluorinated perylene diimides(FPDI-1,FPDI-2) and PPDI were obtained by introducing fluorinated substituents and benzene substituents respectively into the bay of PDI. The optical and electrochemical properties of the three compounds were investigated. In chloroform solution, they all possessed high fluorescence quantum yields(59%-63%) and excellent optical stability. With fluorinated benzene on the bay, the maximum absorption and emission of the FPDIs were both blue-shifted. With the number of fluorine atoms increased, the lowest unoccupied molecular orbital(LUMO) levels of PPDI, FPDI-1 and FPDI-2 reduced gradually from-3.82 e V to-3.96 e V. And the highest occupied molecular orbital(HOMO) levels of the three compounds decreased gradually from-5.89 e V to-6.12 e V.2. By introducing the PEG chains into the end and head of imides, we synthesized the perylene probes(BFPDI-1,BFPDI-2 and BPPDI) with good water-solubility. We investigated their electrochemical-photophysical properties and applications for cellular imaging. With the number of fluorine atoms increased, the fluorescence quantum yields of the three compounds in water were gradually improved from 15% to 36%. They all possessed good water solubility, biocompatibility and pH stability. The brightness of fluorescence images and fluorescence stability in cells were gradually improved with the number of fluorine atoms increased. Among the three probes, the performance of BFPDI-2 was the best.更多还原