近年来，聚集诱导发光（AIE）现象受到了越来越多科研工作者的关注。AIE现象于2001年被唐本忠课题组发现并报道，其与普遍存在的聚集荧光淬灭（ACQ）现象截然相反，这种特殊的光物理性质引起了研究者们的浓厚兴趣，并已被广泛地应用于发光器件和化学生物传感器。在具有AIE性质的化合物中，四苯乙烯（TPE）及其衍生物由于合成相对方便、易水溶性功能化、固态荧光量子产率高等优点而成为AIE研究中最常用的分子。目前已有大量的基于四苯乙烯的功能性AIE分子被设计合成出来，并在多个领域有重要的应用。但是，在生物应用中制约AIE研究的瓶颈之一是：如何增加AIE分子的水溶性。将疏水性的AIE分子与双亲性高聚物包裹制备成为脂质体是解决这一问题的策略之一，但是该方法没有从根本上解决AIE分子的疏水性问题。在AIE母核上引入带（正/负）电荷的基团，以增加其水溶性，但是该方法的普适性有一定的限制。基于本课题组前期糖化学的研究工作，我们设计了通过引入糖类来增加AIE分子的水溶性的新策略，并研究了分子在生物检测中的应用。本论文中采用将乳糖单元引入到TPE母核上的方法使其形成两亲性分子来增大其水溶性，并研究了其在生物检测方面到的应用。 基于烯醛可以与硫醇反应的原理以及糖基的增溶作用，我们首先合成了以TPE为母核，烯醛部分为识别基团以及乳糖基为亲水基团的两亲型荧光探针2OA。探针分子2OA能够在水溶液中自组装为纳米粒子2OA-FON进而发出荧光。2OA-FON与半胱氨酸（Cys）反应后荧光发射峰蓝移了约75 nm，伴随着发光颜色由黄色变为蓝色的显著变化。此外，细胞成像结果表明2OA-FON在活体细胞中检测Cys方面具有潜在应用价值。另外，在第一个分子的基础上，我们将识别基团改为丙二腈使其发射波长红移，设计合成出了另一个水溶性的两亲型荧光探针2CN。其发射波长为620 nm左右，处于红光且接近近红外的范围，初步探索了其生物检测中的应用。 本论文提供了一种发展水溶性AIE型荧光有机纳米粒子探针的通用设计策略，即将亲水性的糖基单元引入到疏水的TPE母核上使其水溶性增大。通过荧光团或者识别基团的改变可以发展出可以检测其他生物活性物种的水溶性纳米粒子探针。

In recent years, the phenomenon of aggregation-induced emission (AIE) has attracted great attention. AIE was discovered and reported by Tang's research group in 2001, which is completely opposite to the ubiquitous phenomenon of aggregation-induced quenching (ACQ). This special photophysical property is of great interest to researchers and has been widely used in luminescent devices and chemical biosensors. Among the compounds with AIE properties, tetraphenylethylene (TPE) and its derivatives have become the most commonly used molecules in AIE research due to their advantages of convenient synthesis, easy functionalization and high solid state fluorescence quantum yield. At present, a great number of functional AIE molecules based on tetraphenylethylene have been designed and synthesized, and have important applications in various fields. However, one of the bottlenecks restricting AIE research in biological applications is how to increase the water solubility of AIE molecules. The encapsulation of hydrophobic AIE molecules with amphiphilic polymers into liposomes is one of the strategies to solve this problem, but this method does not fundamentally solve the hydrophobic problem of AIE molecules. The group with (positive/negative) charges is introduced into the parent nucleus of AIE to increase its water solubility, but the universality of this method has some limitations. Based on the previous research work on carbohydrate chemistry in our research group, we designed a new strategy to increase the water solubility of AIE molecules by introducing sugar moiety, and studied the application of the designed molecules in biological detections. Based on the principle that alkyl aldehyde can react with mercaptan and the solubilization of sugar group, we synthesized an amphiphilic fluorescent probe 2OA with TPE as the parent nucleus, olefin aldehyde as the recognition group and lactose as the hydrophilic group. Probe 2OA can self-assemble into nanoparticle 2OA-FON in aqueous solution and then fluoresce. After the reaction of 2OA-FON with cysteine (Cys), the probe exhibited a 75 nm hypochromatic shift in emission with significant change in luminescence color from yellow to blue. In addition, cell imaging results showed that 2OA-FON had potential application values in detecting Cys in living cells. In addition, we also designed and synthesized another water-soluble amphiphilic fluorescent probe 2CN by changing the recognition group to malononitrile to make its emission wavelength red shift. Its emission wavelength is about 620 nm, which is in the range of near-infrared light. Its application in biological detection was preliminarily explored. This paper provides a general design strategy for the development of water-soluble AIE fluorescent organic nanoparticle probes, in which hydrophilic sugar units are introduced into hydrophobic TPE parent nuclus to increase their water solubility. Water-soluble nanoparticle probes that can detect other bioactive species could be developed by changing the fluorophore or recognition group.