噻吩稠合含硼多环芳香烃的合成及性质研究
发布时间：2019-04-04 15:46
【摘要】：本论文致力于发展新型噻吩硫硼掺杂的有机π共轭体系,主要分为两个部分:第一部分双噻吩稠合1,4-硼硫杂苯的合成及性质研究;第二部分是双苯并噻吩稠合1,4-硼硫杂苯的性质研究。我们成功地合成了上述两种含硼多环芳香烃的母体,并对其光电物理特性进行了深入地研究,探究分子结构与材料性能之间的关系。主要内容如下:在第一部分工作中,我们设计合成了噻吩稠合1,4-硫硼杂苯化合物Ⅰ-1和Ⅰ-2,起初我们采用锡硼交换反应的方法合成了目标化合物,后期为避免使用含锡的有毒试剂,我们对合成方法进行了改进,利用米基硼酸二甲酯作为亲电试剂,两步即可得到目标化合物。随后我们培养并得到了噻吩稠和1,4-硼硫杂苯的同分异构体的单晶,通过对它的单晶进行结构解析,以及结合理论计算,我们认为噻吩稠合1,4-硼硫杂苯具有弱的芳香性。我们还对其光电物理性质进行了详细的研究。研究发现,利用碱拔氢/亲电体捕捉以及Stille偶联反应可以对Ⅰ-1和Ⅰ-2的2,4-位置进行衍生化。我们也同时对部分衍生物进行了光电物理性质的研究。研究发现,Ⅰ-1和Ⅰ-2在引入取代基之后吸收和发射波长均会显示一定程度的红移。另外,对于Ⅰ-1和Ⅰ-2作为氟离子传感器也进行了初步地研究,我们发现加入F-后,Ⅰ-1和Ⅰ-2的吸收和发射受到明显的抑制,此性质表明Ⅰ-1和Ⅰ-2中的硼原子仍然具有一定的Lewis酸性。在第二部分工作中,基于第一部分工作的基础,我们设计并合成苯并噻吩稠合1,4-硫硼杂环化合物Ⅱ-1和Ⅱ-2,随后利用同样新的方法得到了目标产物,我们也对Ⅱ-1和Ⅱ-2的单晶结构进行了详细的研究,并且测试了Ⅱ-1和Ⅱ-2的紫外吸收、荧光发射、与F-络合后的吸收发射以及循环伏安曲线。研究发现,苯并噻吩稠和的1,4-硼硫杂苯的光电物理性质与硼硫的相对位置有很大的关系。此外,此类化合物在空气中非常稳定,可以作为并五苯的类似物。总之,本论文围绕噻吩稠和的含硼多环芳烃进行了研究,设计并合成了两个系列含硼的多环芳香烃,研究了其结构与性质的关系,为后续将此类多环共轭芳香烃应用到有机光电材料中去奠定了一定的基础。
[Abstract]:The present paper is devoted to the development of a new type of organosulfur-boron-doped organic carbon-benzene system, which is mainly divided into two parts: the synthesis and properties of the fused 1,4-boron-thiazene in the first part, and the properties of the 1,4-boron-thiazene fused by the second part. In this paper, we successfully synthesized the parent of the two kinds of boron-containing polycyclic aromatic hydrocarbons, and carried out in-depth study on the photoelectric physical properties of the two kinds of boron-containing polycyclic aromatic hydrocarbons, and explored the relationship between the molecular structure and the material property. The main contents are as follows: In the first part of the work, we designed the compound I-1 and I-2 of the 1,4-thiobo-benzo-benzo-azobenzene compounds I-1 and I-2, at the beginning, we synthesized the target compound by the method of the tin-boron exchange reaction, and the later period is to avoid the use of the tin-containing toxic reagent. The synthesis method is improved, and the target compound can be obtained in two steps by using the methyl-based boric acid dimethyl ester as the electrophilic reagent. The single crystals of the isomers of 1,4-boron-thiazobenzene are then cultured and obtained. By structural analysis of its single crystal and the theoretical calculation, we consider that the 1,4-boron-thiazene has a weak aromaticity. We have also studied the photoelectrical properties in detail. It is found that the 2,4-position of I-1 and I-2 can be derivatised by means of alkaline extraction of hydrogen/ electrophile capture and the Stille coupling reaction. We also study the photoelectrical properties of some of the derivatives at the same time. It was found that the absorption and emission wavelength of I-1 and I-2 after the introduction of the substituents showed a certain degree of redshift. In addition, I-1 and I-2 were also studied as a fluoride ion sensor. We found that the absorption and emission of I-1 and I-2 were significantly inhibited after F-1 and I-2, which indicated that the boron atoms in I-1 and I-2 still have a certain Lewis acidity. in that work of the second part, based on the basis of the work of the first part, we design and synthesize the benzo-1,4-thiobo-heterocyclic compound II-1 and II-2, and then using the same new method to obtain the target product, We also studied the single crystal structure of 鈪，
本文编号：2453956
[Abstract]:The present paper is devoted to the development of a new type of organosulfur-boron-doped organic carbon-benzene system, which is mainly divided into two parts: the synthesis and properties of the fused 1,4-boron-thiazene in the first part, and the properties of the 1,4-boron-thiazene fused by the second part. In this paper, we successfully synthesized the parent of the two kinds of boron-containing polycyclic aromatic hydrocarbons, and carried out in-depth study on the photoelectric physical properties of the two kinds of boron-containing polycyclic aromatic hydrocarbons, and explored the relationship between the molecular structure and the material property. The main contents are as follows: In the first part of the work, we designed the compound I-1 and I-2 of the 1,4-thiobo-benzo-benzo-azobenzene compounds I-1 and I-2, at the beginning, we synthesized the target compound by the method of the tin-boron exchange reaction, and the later period is to avoid the use of the tin-containing toxic reagent. The synthesis method is improved, and the target compound can be obtained in two steps by using the methyl-based boric acid dimethyl ester as the electrophilic reagent. The single crystals of the isomers of 1,4-boron-thiazobenzene are then cultured and obtained. By structural analysis of its single crystal and the theoretical calculation, we consider that the 1,4-boron-thiazene has a weak aromaticity. We have also studied the photoelectrical properties in detail. It is found that the 2,4-position of I-1 and I-2 can be derivatised by means of alkaline extraction of hydrogen/ electrophile capture and the Stille coupling reaction. We also study the photoelectrical properties of some of the derivatives at the same time. It was found that the absorption and emission wavelength of I-1 and I-2 after the introduction of the substituents showed a certain degree of redshift. In addition, I-1 and I-2 were also studied as a fluoride ion sensor. We found that the absorption and emission of I-1 and I-2 were significantly inhibited after F-1 and I-2, which indicated that the boron atoms in I-1 and I-2 still have a certain Lewis acidity. in that work of the second part, based on the basis of the work of the first part, we design and synthesize the benzo-1,4-thiobo-heterocyclic compound II-1 and II-2, and then using the same new method to obtain the target product, We also studied the single crystal structure of 鈪，
本文编号：2453956
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