二聚型罗丹明类荧光探针的设计

The Design of Fluorescent Probe Based on Dimer-rhodamine Derivatives

向威

11749051

硕士

化学

黄文忠

2019-05-20

2019-07-10

哈尔滨工业大学

深圳

生物体内的各种阴、阳离子，氨基酸以及蛋白质等的含量对生命健康的维持起到了重要作用，如果能便捷地检测这些物质在生物体内的分布及浓度变化，则对于它们能引起的疾病的预防和控制起到非常重要的作用。因此，发展能快速、准确、无损、原位地检测这些物质的分析方法便成为研究者们关注的重点。小分子荧光探针技术作为一种新兴的分析检测技术，因其反应灵敏，准确度高，检出限较低且能运用于生物体荧光成像等优点，吸引了众多研究者们的目光并发展成为一项独立的分析技术。罗丹明是一种常见的生物荧光染色剂，具有许多优良的光学性质，如：较大的摩尔吸收系数和荧光量子产率，较好的光稳定性等。因此，罗丹明常常作为荧光母体被运用于荧光探针的设计及构建中。由于基于罗丹明衍生物的荧光探针有固定的氧杂蒽发色团，因此吸收和发射光的波长变化并不大，吸收光波长通常在550nm附近，发射光波长通常在570nm附近。但是在荧光探针运用于生物成像中时，较大的吸收光波长能有效地降低生物自发光带来的影响且能提高信噪比。理论上，更大的共轭结构能使得荧光探针的吸收光波长更大，即红移。基于此，本论文在前人的基础上，设计开发了一对基于二聚罗丹明衍生物的荧光探针，它们是一对顺反异构体，都以二聚形式的氧杂蒽为其发色主体。实验数据表明，这对顺反异构体在光物理、光化学性质方面存在较大差别，反式的荧光探针显示出对钯离子具有很好的选择性，而且由于这对荧光探针的荧光团具有更大刚性平面结构，使得荧光探针开环时产生的最大吸收波长红移，达到603 nm，荧光发射峰的位置达到625 nm，相比于普通罗丹明的吸收和发射峰的位置红移达50 nm左右，具有更好的应用前景。

The content of various anion, cation, amino acids and proteins in organisms plays an important role in the maintenance of life and health. If the distribution and concentration of these substances in organisms can be easily detected, it will play a very important role in the prevention and control of the diseases they can cause. Therefore, the development of rapid, accurate, non-destructive, in situ detection of these substances analysis methods have become the focus of researchers' attention. Small molecule fluorescence probe technology, as a new analytical and detection technology, has attracted the attention of many researchers and developed into an independent analytical technique because of its sensitive, high accuracy, low detection limit and its ability to be used in fluorescent imaging of organisms.Rhodamine is a common biological fluorescence dyes with many excellent optical properties, such as: larger molar absorption coefficient and fluorescence quantum yield, better photo stability and so on. Therefore, rhodamine is often used as a fluorescent matrix in the design of fluorescent probes. Because fluorescent probes based on rhodamine derivatives contain inherent xanthene, the wavelength of absorption and emitting varies little, the wavelength of absorption is usually near 550 nm, and the wavelength of emitting is usually near 570 nm. However, when fluorescent probes are used in biological imaging, the large absorption wavelength can effectively reduce the effect of biological spontaneous light and improve the signal-to-noise ratio. Theoretically, an extended conjugate structure can make the absorption wavelength of a fluorescent probe shift to red. Based on this, On the basis of the predecessors, this paper designs and develops a pair of fluorescent probes based on dimer rhodamine derivatives, which are a pair of cis and trans isomers, the fluorophore of them are dimer-oxanthone. The experimental data show that there are great differences in the photophysical and photochemical properties of the isomers, the trans fluorescence probe shows a good selectivity to palladium ions, and as the fluorescent probe has a larger rigid plane fluorophore, which makes the maximum absorption wavelength red shift, reaching 603 nm, The position of the fluorescence emission peak reaches 625 nm, and the position of the absorption and emission peaks of the normal rhodamine is about a red shift of about 50 nm.

罗丹明 荧光探针 钯离子检测 红移

rhodamine fluorescent probe sensing of palladium ions red shift

中文

联合培养

南方科技大学

向威. 二聚型罗丹明类荧光探针的设计[D]. 深圳. 哈尔滨工业大学,2019.