芳炔基化合物的化学发光和圆偏振发光研究

化学发光种类繁多，常见的有二氧杂环丁烷类、草酸酯类、鲁米诺和吖啶酯等。化学发光不需要激发光源，因此其在生物成像中有着巨大的应用潜力。而在探针的应用中，除了发光强度、发光波长和发光寿命，圆偏振程度也可以作为信号维度。本文制备了一系列结构各异但基本以炔键为联结单元的分子，研究了这些分子的化学发光、圆偏振发光或者圆偏振化学发光性质，探索分子的化学结构对发光性质的影响。结合对环芳烷骨架成功制备了手性二氧杂环丁烷分子，实现了化学触发型圆偏振化学发光，研究化学发光的动力学和激发态性质，以“看到化学发光的中间体”；制备了平面手性大环荧光分子，将其作为激活剂成功实现了草酸酯的圆偏振化学发光，研究激活剂的氧化还原性质以提高化学发光效率。引入金属制备了新型二氧杂环丁烷分子，研究炔键和金属对化学发光的影响，实现了化学发光效率和速率的调节。制备了平面手性金配合物，探索分子结构、激发态性质和磁场对圆偏振发光的影响。具体研究内容如下：

通过炔键或者双键将手性对环芳烷骨架引入Schaap二氧杂环丁烷，制备了具有光学活性的二氧杂环丁烷C1R/C1S-C4R/C4S。经TBAF脱除TBS保护基触发后，C1R和C3R发出绿光和黄光，其化学发光峰和发光效率分别为497 nm/537 nm和7%/1.5%。完整地记录了化学发光圆偏振信号随波长和时间变化的谱图，双取代的C1R/C1S和C3R/C3S的圆偏振化学发光不对称因子分别为+1.1´10^‒3/-1.0´10^‒3和+6.0´10^‒4/-5.0´10^‒4。动力学研究显示，圆偏振化学发光信号随着时间而衰减，但其不对称因子一直保持不变，在将来的分析应用中，这一性质可以作为新的内标参数。研究了光致激发态和化学激发态的紫外-可见吸收、圆二色、光致/化学发光和圆偏振光致/化学发光光谱，在本例中，实验表明可以通过光致激发态来模拟研究化学激发态的性质。手性结构相似的C12R和C14R分别具有两个和一个苯酚生色团，但其圆二色吸收和圆偏振发光光谱展现出明显的差异，TDDFT计算很好地复现了实验结果，而且表明C12R存在激子耦合现象，这对于将来设计更优秀的圆偏振光致/化学发光分子具有指导意义。

以手性对环芳烷为骨架，以炔基为支臂制备了带有给电子取代基的大环分子（D1R/D1S-D4R/D4S）以及手性螺烯分子（D5P/D5M），这些分子的光致发光量子效率在17%—41%之间，圆二色吸收不对称因子和圆偏振发光不对称因子分别在5.0´10^‒3和4.0´10^‒3左右。将其作为荧光受体（激活剂）应用于草酸酯化学发光体系中，观察到了强度不等的草酸酯化学发光，通过调整催化剂和荧光分子的种类和浓度，草酸酯和过氧化氢的浓度，可以调节化学发光的瞬时强度、总强度和持续时间。通过比较法测定了其化学发光量子效率（F_CL），D1R, D2R, D3R, D4R和D5P 在浓度为1.0´10^‒4 mol dm^-3时的F_CL分别为8.2´10^‒5, 2.1´10^‒3, 5.5´10^‒6, 2.7´10^‒4和2.8´10^‒4。结果发现，在一定的激活剂浓度下，ln(F_S)（F_S为单线态量子效率）和E_p/2（半峰氧化电位）呈负相关关系，氧化电位越低，化学发光效率越高。研究了这些手性激活剂的圆偏振化学发光性质，记录到了明确且镜像对称的圆偏振信号，这是第一次观察到了草酸酯化学发光的圆偏振信号，其不对称因子g_CL稍小于光致圆偏振发光不对称因子（g_PL），且不随时间改变，这些发现对于设计更优秀的草酸酯圆偏振化学发光分子以及将其应用于实践中有借鉴意义。

在苯酚基二氧杂环丁烷的羟基邻位引入炔基制备了E6，使其在二甲基亚砜溶液中的化学发光效率提高了20倍。而且，以炔基作为连接体，成功制备了含有一价金（Au）和二价铂（Pt）的二氧杂环丁烷分子E8和E10，研究具有较大自旋轨道耦合参数（SOC）的金属对化学发光的影响。实验结果发现，金属的引入使得化学发光时间缩短至原来的十分之一，化学发光由辉光型转变为闪光型。在空气氛条件下的发光效率降低，因为重原子效应促进了系间窜越过程导致较多的三线态，其被空气淬灭牺牲了化学发光效率。通过监测化学发光反应过程中吸收光谱的变化，观察到了E6分解过程中间体的吸收峰。分解产物E11的斯托克斯位移达到了10693 cm^-1，可归因于激发态分子内质子转移。

基于手性对环芳烷通过炔键的配位制备了手性多核金（Ⅰ）配合物（F2R/F2S-F6R/F6S）及其相应的模型配合物（F1A和F1B），详细的光物理性质研究表明，分子空间排列方式和与金的配位与否都能调控手性光谱的正负符号。这些金（Ⅰ）配合物展现出荧光-磷光双发射现象，通过调节核数，可以调节荧光-磷光的强度比例；荧光-磷光展现出不一样的圆偏振发光和磁圆偏振发光性质，在无外磁场存在时，荧光区有比较明显的CPL信号，磷光区没有或只有很微弱的CPL信号；在外磁场存在时，荧光区CPL信号不受影响，磷光区展现处明显的CPL信号，CPL的符号由磁场控制。实验结果表明，分子结构、激发态性质和外磁场都能影响圆偏振发光的性质，对称性的降低有利于圆偏振信号的增强。

Chemiluminescence encompasses a wide range of types, including dioxetanes, peroxyoxalates, luminol, and acridinium esters. Chemiluminescence does not require an excitation source, thus having great application potential in biological imaging. In application of the probe, the intensity, wavelength, and lifetime of the emitted light are commonly used signal dimensions. Additionally, circular polarization can serve as a valuable signal dimension. This dissertation presents the synthesis of a series of novel molecules with different structures but basically linked by alkynyl unit, which either possess both chemiluminescence and circularly polarized luminescence properties, or only one of the two, to explore the influence of molecular chemical structure on luminescent properties. By combining the [2.2]paracyclophane skeleton, chiral dioxetanes were successfully prepared, achieving chemically triggered circularly polarized luminescence. The kinetics and excited state properties of chemiluminescence were studied to "observe the intermediate of chemiluminescence. Planar chiral macrocyclic fluorescent molecules were synthesized and used as activators to achieve circularly polarized peroxyoxalate chemiluminescence. The redox properties of the activators were studied to improve the efficiency of chemiluminescence. Introduction of metals led to the preparation of new dioxetanes, and the effects of acetylene bond and metals on chemiluminescence were studied, realizing the regulation of chemiluminescence efficiency and rate. Planar chiral gold complexes were prepared to explore the influence of molecular structure, excited state properties, and magnetic field on circularly polarized luminescence. The research contents are specified as follows:

Optical-active dioxetanes, C1R/C1S-C4R/C4S, were synthesized by introducing a chiral [2.2]paracyclophane skeleton into Schaap dioxetane through triple or double bonds. Upon triggering with TBAF, C1R and C3R emitted green and yellow light, with chemiluminescent peaks at 497 nm/537 nm and efficiencies of 7%/1.5%, respectively. Circularly polarized chemiluminescence signals vs wavelength and time were completely recorded. The circular polarization asymmetry factors for C1R/C1S and C3R/C3S were determined to be +1.1´10^‒3/-1.0´10^‒3 and +6.0´10^‒4/-5.0´10^‒4, respectively. Kinetic studies revealed that while the circularly polarized chemiluminescent signal decayed over time, its asymmetry factor remained constant. This property can serve as a new internal standard parameter in future analytical applications. The UV-Vis absorption, circular dichroism, photo/chemical-luminescence, and circularly polarized photo/chemical-luminescence spectra of the photoexcited and chemically excited states were investigated, and it was found that the properties of the chemically excited state can be simulated by studying the photoexcited state. C12R and C14R, which have similar chiral structures but differ in the number of phenol chromophores (two and one, respectively), exhibited significant differences in their circular dichroism absorption and circularly polarized luminescence spectra. TDDFT calculations successfully reproduced the experimental results and indicated the presence of exciton coupling in C12R, which provides guidelines for the future design of circularly polarized photo/chemical-luminescent molecules.

Chiral macrocyclic molecules (D1R/D1S-D4R/D4S) based on chiral [2.2]paracyclophane and alkynyl unit with electron-donating substituents and chiral helicenes (D5P/D5M) were synthesized. These molecules exhibited moderate photoluminescence quantum efficiency (17%-41%) and relatively high chiroptical properties, with circular dichroism absorption asymmetry factors around 5.0×10^‒3 and circularly polarized luminescence factors around 4.0×10^‒3. When applied as fluorescent receptors (activators) in peroxyoxalate chemiluminescent systems, chemiluminescence was observed. By adjusting the catalyst and fluorophore types and concentrations, as well as the concentrations of peroxyoxalate and hydrogen peroxide, the instantaneous intensity, total intensity, and duration of chemiluminescence could be modulated. The chemiluminescent quantum efficiency (Φ_CL) of D1R, D2R, D3R, D4R, and D5P at a concentration of 1.0×10^‒4 mol dm^‒3 was determined by comparative methods, resulting in values of 8.2×10‒5, 2.1×10^‒3, 5.5×10^‒6, 2.7×10^‒4, and 2.8×10^‒4, respectively. The results indicated that, at a certain activator concentration, ln(Φ_S) (Φ_S being singlet state quantum efficiency) and E_p/2 (half-wave oxidation potential) exhibited a negative correlation, where lower oxidation potentials corresponded to higher chemiluminescent efficiencies. The circularly polarized chemiluminescence of these chiral activators were studied, clear and mirror-symmetric circularly polarized signals were recorded. The asymmetry factor g_CL for circularly polarized chemiluminescence was slightly smaller than the g-factor for photoexcited circularly polarized luminescence (g_PL) and remained constant over time. These findings are of practical significance for designing better peroxyacetate circularly polarized chemiluminescent molecules and applying them in practice.

The introduction of an alkynyl moiety at the hydroxyl o-position of phenol-based dioxetane has resulted in the synthesis of E6, which exhibits a 20-fold improvement in chemiluminescent efficiency in dimethyl sulfoxide solution. Additionally, using the alkynyl group as a linker, we successfully prepared dioxetane molecules, namely E8 and E10, incorporating monovalent gold Au(Ⅰ) and divalent platinum Pt(Ⅱ), respectively, to investigate the influence of heavy metal atoms on chemiluminescence. Experimental results revealed that the introduction of metal atoms led to a significant reduction in the chemiluminescence duration to approximately one-tenth of its original value, transforming the chemiluminescence from glow-type to flash-type. The efficiency of chemiluminescence under atmospheric conditions decreased, which we attributed to the heavy atom effect resulting in the generation of more triplet states that were quenched by air, thereby sacrificing the chemiluminescent efficiency. By monitoring changes in the absorption spectra during the chemiluminescent reaction, we observed absorption peaks corresponding to intermediates involved in the decomposition process of E6. The Stokes shift of the decomposition product E11 reached 10693 cm^-1, which can be attributed to excited-state intramolecular proton transfer (ESIPT).

Chiral multinuclear gold (I) complexes (F2R/F2S-F6R/F6S) and their corresponding model complexes (F1A and F1B) were prepared based on chiral [2.2]paracyclophane and alkynyl bonds. Detailed photophysical studies revealed that the spatial arrangement of molecules and their coordination to gold could regulate the sign of chiroptical spectra. These gold (I) complexes exhibited fluorescence-phosphorescence dual emission phenomena, and the intensity ratio of fluorescence to phosphorescence could be adjusted by tuning the number of cores. Fluorescence and phosphorescence demonstrated different circularly polarized luminescence and magnetic circularly polarized luminescence. In the absence of an external magnetic field, the fluorescence region exhibited significant circularly polarized luminescence (CPL) signals, while the phosphorescence region either had no CPL signal or only a weak one. In the presence of an external magnetic field, the CPL signal in the fluorescence region remained unaffected, while the phosphorescence region showed a pronounced CPL signal. Experimental results indicated that molecular structure, excited state properties, and external magnetic fields can all influence the properties of circularly polarized luminescence, and the reduction of symmetry is beneficial for enhancing the circularly polarized signal.

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