氟硼二吡咯（BODIPY）荧光染料从发现以来，凭借其优良的光物理性质广泛应用于离子检测、小分子化合物的识别、pH 的检测以及生物体细胞器定位等方面。但是，传统BODIPY 探针的聚集诱导淬灭效应（ACQ）以及其窄的吸收和发射波长（一般在 480-530 nm之间），在一定程度上限制了 BODIPY 探针的实际应用。为了避免 BODIPY 的聚集诱导淬灭效应和光散射引起的荧光检测不足，一些研究者将研究重点放在了多荧光团荧光探针分子的设计与合成上，期望合成出在近红外波长范围内发光的化合物，由此罗丹明、香豆素、卟啉等发光团修饰的 BODIPY 类化合物得到了发展。但是，目前多荧光团探针分子设计仍有待深入，其应用范围远没有单荧光团 BODIPY 探针的应用范围广。基于本课题组前期系列咔唑类化合物和水溶性四苯乙烯探针的设计与研究，我们以咔唑、四苯乙烯分别修饰BODIPY 得到多荧光团的 BODIPY 化合物。本论文分为下面两部分：
第一部分：合成了 BODIPY-咔唑衍生的探针分子，BDP-Zn 2+ ,该化合物是以 BODIPY和咔唑为荧光团，N,N-双（2-吡啶甲基）乙基胺（BPEA）为 Zn 2+ 识别基团，络合 Zn 2+ 后得到的。基于四种类型表面活性剂 SDS、DTAB、BS-12 和 Triton X-100 在溶液中形成的微环境不同，在一定浓度下探针分子 BDP-Zn 2+ 实现了对这四种表面活性剂的区分，并且肉眼即可观测到荧光颜色的差异。另外，利用表面活性剂加入后探针荧光强度的增加以及在514 nm 和 607 nm 波长下荧光强度的比值变化两种方法，实现了对四种表面活性剂临界胶束浓度（CMC）的测定。该工作提供了一种可以有效区分四种表面活性剂并研究其相关物理化学性质的高效检测方法。
第二部分：采用模块化合成策略，通过经典的 Suzuki 反应或 Knoevenagel 反应将糖基四苯乙烯（TPE）单元引入到 BODIPY 中，增大其共轭体系，合成了乳糖修饰的水溶性BODIPY-TPE 探针分子，4B2OT 和 2B3OT。基于羧酸酯和羧酸根对荧光团推拉电子能力的差异，在水溶液中，酯酶可以将 BODIPY 的 meso 位的羧酸酯（具有较强的拉电子能力）水解为羧酸根离子（具有给电子能力），从而使得整个探针分子的荧光光谱发生蓝移。初步测试显示，2B3OT 有望实现对猪肝酯酶（PLE）的比率型响应，下一步将继续深入研究其性质与应用。

 Since the discovery of BODIPY fluorescence dyes, it has been widely used in many fields, such as detecting ions, recognizing small molecule compounds, measuring pH and locating organelles due to its excellent photophysical properties. However, the aggregation induced quenching (ACQ) effect of traditional BODIPY dye and its short absorption and emission wavelengths (generally between 480 nm to 530 nm) limited its practical applications. In order to avoid the shortages of fluorescence detection caused by aggregation induced quenching effect of BODIPY and light scattering, some researchers focused on the design and synthesis of multi-fluorophore containing fluorescent probe molecules. It is expected to synthesize probes with near-infrared wavelength range, as a result, a series of BODIPY compounds modified by luminescent groups such as rhodamine, coumarin, and porphyrin have been developed. However, the molecular design of multi-fluorophore probes still needs to be explored deeply, their application range was far less than that of single fluorophore BODIPY probes. Based on the previous works of our group on carbazoles and water-soluble tetraphenylethylene, we designed and synthesized BODIPY compounds modified by carbazole and tetraphenylethylene (TPE) respectively. The content in this thesis can be divided into the following two parts:
In the first part, we synthesized a BODIPY-carbazole probe, named as BDP-Zn 2+ . It was composed of covalently linked BODIPY, carbazole, N,N-bis(2-pyridylmethyl)ethylenediamine (BPEA) and zinc ion to fabricate a novel push-pull molecular structure. BDP-Zn 2+ could be used to discriminate four different types of surfactants (SDS, DTAB, BS-12, Triton X-100) based on the different micro-environments formed by the four types of surfactant in aqueous solution, and the naked eye can observe the different colors changes. Besides, the CMC of surfactants could be identified by the fluorescence enhancement and the ratio of fluorescence intensity at 607 nm to 514 nm of BDP-Zn 2+ . This work offered a useful and powerful detection strategy for the further study of physical and chemical behaviors of different surfactants.

In the second part, we designed and synthesized water-soluble BODIPY-TPE fluorescent probes, 4B2OT and 2B3OT. The molecules were composed of covalently linked sugar groups, TPE and BODIPY to fabricated the large conjugated system by using modular synthesis strategy via classic Suzuki or Knoevenagel reaction. Based on the difference in the push-pull electrons III ability of carboxylic ester and carboxylate groups, the esterase catalyzed ester (strong electron pulling ability) to carboxylic acid (electron donoring ability) which led to a blue shift in the fluorescence spectrum in aqueous solution, we expected 4B2OT and 2B3OT could be used for pig liver esterase (PLE) detection. The preliminary results showed that only 2B3OT responded to PLE and could be used for ratiometric detection of PLE. Its characteristics and application in biological area will be further studied.