含三嗪环的氮杂环蕃化合物的合成与研究
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摘要
超分子化学是一门研究多个分子通过非共价键作用而形成的功能体系的科学。超分子化学的发展不仅与大环化学(冠醚、穴醚、环糊精、杯芳烃等)的发展有着密切的联系,而且还与分子组装(双分子膜等)、分子器件与新兴有机材料的研究息息相关。
环蕃化合物是在主-客体化学研究中充当主体的一类重要化合物,也是人类模拟酶研究中发现的一类重要化合物。环蕃因为其自身结构的灵活多样和分子空腔的可调控性,在模拟酶、主-客体化学、分子自组装、选择性催化和材料科学等方面有着广泛的潜在应用前景。
本论文通过三聚氯氰、1,6-己二胺、4,4'-二胺基二苯甲烷、十二胺等一些简单的化合物为原料,合成出新型的含三嗪环的氮杂环蕃化合物,并对其与金属阳离子络合进行了研究。全文共分为三部分。第一部分概括的介绍了超分子化学、环蕃化学、手性化学；在介绍超分子化学时,讲述了超分子的一些基本功能、列举了超分子化学当中的一些主体化合物(如冠醚及其衍生物、杯芳烃、环糊精)；在列举杯芳烃时,又对其与中性分子、阴离子和阳离子的识别简单做了一些介绍；最后由于越来越多化学家研究手性化合物,因此简单介绍了几类手性化合物如手性冠醚、手性杯芳烃、手性大环多胺。第二部分是实验部分,本部分主要以三聚氯氰、1,6-己二胺等一些简单原料合成几种含三嗪环的氮杂环蕃环蕃化合物；在合成含三嗪环的氮杂环蕃环蕃化合物的中间体时,发现它的溶解度非常差,因此用十二胺对其三嗪环进行了修饰,改变其溶解性,结果也证明了,合成出的三嗪环的氮杂环蕃环蕃化合物溶解性比较好,易溶于氯仿、乙酸乙酯、甲醇等有机溶剂,并用飞行质谱、红外、核磁等对产物进行了表征。第三部是用合成的含三嗪环的氮杂环蕃化合物作为受体,用Zn2+、Fe3+、Cu2+、Mn2+这几种金属进行络合的探索性试验,结果也显示了合成出的含三嗪环的氮杂环蕃环蕃化合物与这几种金属离子络合了。
Supramolecular chemistry is the study of multiple molecules to pass through the role of non-covalent bonds formed by functional system of science. The development of supramolecular chemistry is not only closely linked to macrocyclic chemistry(crown ethers, cryptands, cyclodextrins, calixarene, etc.), but also with the molecular assembly(bilayer membrane, etc.), molecular devices and the emerging organic materials research are closely related.
Cyclophane compounds in the host-guest chemistry research as an important class of compounds, the subject is human enzymes found in the simulation of an important class of compounds. Cyclophane because of its flexible structure and its molecular regulation of the cavity can be in the simulated enzyme, host-guest chemistry, molecular self-assembly, selective catalytic and materials science habnve a wide range of potential applications.
The dissertation by cyanuric chloride,1,6-hexanediamine,4,4'-diaminodiphenyl methane, laurylamine and some simple compounds have synthesized a novel azacyclophane compounds containing triazine ring, and its complexation with metal ions were studied. The dissertation is divided into three chapters. The first part describes the supramolecular chemistry, cyclophane chemistry, chiral chemistry. Some of the basic functions of supramolecular chemistry and some of the main compounds (such as crown ethers and their derivatives, calixarene, CD) was described in the introduction of supramolecular Chemistry. When the calixarene in the list, its neutral molecules, anions and cations do recognize simple introduction. Finally, as more and more chemists study chiral compounds, so a brief introduction of several classes of chiral compounds such as chiral crown ethers, chiral calixarene, chiral macrocyclic polyamine. The second part is the experimental section. This section we have synthesized several simple novel azacyclophane compounds containing triazine ring by using cyanuric chloride,1,6-hexanediamine as raw materials. When I have synthesized azacyclophane intermediate compounds containing triazine ring, I found it very poor solubility. So its triazine ring was modified to change the solubility by using the laurylamine. The results also proved that it has a better solubility. It is soluble in chloroform, ethyl acetate, methanol and other organic solvents. The products structures were characterized by MALDI-TOFMS, IR,1H NMR, etc. The third part is the synthesis of azacyclophane compounds containing triazine ring as a receptor, with Zn2+, Fe3+, Cu2+, Mn2+ complexation of these types of metals to explore the line test. The results also show that the synthesized azacyclophane compounds containing triazine ring is together by metal ions.
环蕃化合物是在主-客体化学研究中充当主体的一类重要化合物,也是人类模拟酶研究中发现的一类重要化合物。环蕃因为其自身结构的灵活多样和分子空腔的可调控性,在模拟酶、主-客体化学、分子自组装、选择性催化和材料科学等方面有着广泛的潜在应用前景。
本论文通过三聚氯氰、1,6-己二胺、4,4'-二胺基二苯甲烷、十二胺等一些简单的化合物为原料,合成出新型的含三嗪环的氮杂环蕃化合物,并对其与金属阳离子络合进行了研究。全文共分为三部分。第一部分概括的介绍了超分子化学、环蕃化学、手性化学；在介绍超分子化学时,讲述了超分子的一些基本功能、列举了超分子化学当中的一些主体化合物(如冠醚及其衍生物、杯芳烃、环糊精)；在列举杯芳烃时,又对其与中性分子、阴离子和阳离子的识别简单做了一些介绍；最后由于越来越多化学家研究手性化合物,因此简单介绍了几类手性化合物如手性冠醚、手性杯芳烃、手性大环多胺。第二部分是实验部分,本部分主要以三聚氯氰、1,6-己二胺等一些简单原料合成几种含三嗪环的氮杂环蕃环蕃化合物；在合成含三嗪环的氮杂环蕃环蕃化合物的中间体时,发现它的溶解度非常差,因此用十二胺对其三嗪环进行了修饰,改变其溶解性,结果也证明了,合成出的三嗪环的氮杂环蕃环蕃化合物溶解性比较好,易溶于氯仿、乙酸乙酯、甲醇等有机溶剂,并用飞行质谱、红外、核磁等对产物进行了表征。第三部是用合成的含三嗪环的氮杂环蕃化合物作为受体,用Zn2+、Fe3+、Cu2+、Mn2+这几种金属进行络合的探索性试验,结果也显示了合成出的含三嗪环的氮杂环蕃环蕃化合物与这几种金属离子络合了。
Supramolecular chemistry is the study of multiple molecules to pass through the role of non-covalent bonds formed by functional system of science. The development of supramolecular chemistry is not only closely linked to macrocyclic chemistry(crown ethers, cryptands, cyclodextrins, calixarene, etc.), but also with the molecular assembly(bilayer membrane, etc.), molecular devices and the emerging organic materials research are closely related.
Cyclophane compounds in the host-guest chemistry research as an important class of compounds, the subject is human enzymes found in the simulation of an important class of compounds. Cyclophane because of its flexible structure and its molecular regulation of the cavity can be in the simulated enzyme, host-guest chemistry, molecular self-assembly, selective catalytic and materials science habnve a wide range of potential applications.
The dissertation by cyanuric chloride,1,6-hexanediamine,4,4'-diaminodiphenyl methane, laurylamine and some simple compounds have synthesized a novel azacyclophane compounds containing triazine ring, and its complexation with metal ions were studied. The dissertation is divided into three chapters. The first part describes the supramolecular chemistry, cyclophane chemistry, chiral chemistry. Some of the basic functions of supramolecular chemistry and some of the main compounds (such as crown ethers and their derivatives, calixarene, CD) was described in the introduction of supramolecular Chemistry. When the calixarene in the list, its neutral molecules, anions and cations do recognize simple introduction. Finally, as more and more chemists study chiral compounds, so a brief introduction of several classes of chiral compounds such as chiral crown ethers, chiral calixarene, chiral macrocyclic polyamine. The second part is the experimental section. This section we have synthesized several simple novel azacyclophane compounds containing triazine ring by using cyanuric chloride,1,6-hexanediamine as raw materials. When I have synthesized azacyclophane intermediate compounds containing triazine ring, I found it very poor solubility. So its triazine ring was modified to change the solubility by using the laurylamine. The results also proved that it has a better solubility. It is soluble in chloroform, ethyl acetate, methanol and other organic solvents. The products structures were characterized by MALDI-TOFMS, IR,1H NMR, etc. The third part is the synthesis of azacyclophane compounds containing triazine ring as a receptor, with Zn2+, Fe3+, Cu2+, Mn2+ complexation of these types of metals to explore the line test. The results also show that the synthesized azacyclophane compounds containing triazine ring is together by metal ions.
引文
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