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中文题名:

 手性大环的合成及性质研究    

姓名:

 李妍静    

保密级别:

 公开    

论文语种:

 chi    

学科代码:

 070301    

学科专业:

 化学    

学生类型:

 学士    

学位:

 理学学士    

学位年度:

 2023    

校区:

 北京校区培养    

学院:

 化学学院    

研究方向:

 有机化学    

第一导师姓名:

 江华    

第一导师单位:

 化学学院    

提交日期:

 2023-06-05    

答辩日期:

 2023-05-17    

外文题名:

 Synthesis and Properties of the Chiral Macrocycle    

中文关键词:

 手性 ; 环对苯撑 ; 碳纳米环 ; Diels-Alder反应    

外文关键词:

 Chirality ; Cycloparaphenylenes ; Carbon macrocycles ; Diels-Alder reaction    

中文摘要:

碳纳米管(CNTs)具有优异的性能,被广泛应用于材料、生物、催化和电子等多个领域。由多个苯环对位连接而成的环对苯撑(Cycloparaphenylenes, CPPs)被认为是扶手椅型碳纳米管(CNTs)最简单的基元,开发手性CPP大环能为自下而上合成手性碳纳米管提供可能,因此备受科学家的关注。目前,构建手性大环主要有两种方式,一是引入非手性基元,利用空间位阻限制破坏大环本身高度对称性,形成固有手性;二是直接引入手性基元。已报道的大部分手性大环均是在CPP环进行芳构化之前就引入了构建基元。在本课题中,我们设计了一种新型手性CPP大环,选取了经典的甲氧基修饰的环己二烯单元作为前体,将氧化噻吩结构引入CPP骨架中,通过Diels-Alder后修饰反应,引入手性基元,从而制备具有R*基取代的邻苯二甲酰亚胺结构的大环,为合成多样手性基团的大环化合物提供便利,也为后续研究提供备选材料和新思路。

外文摘要:

Carbon nanotubes (CNTs) having excellent properties are widely used in many fields, such as materials, biology, catalysis and electronics. Cycloparaphenylenes (CPPs) formed by para-position connection of several benzene rings are considered as the simplest structural units of armchair carbon nanotubes. The development of chiral CPP macrocycles can provide the possibility for the bottom-up synthesis of chiral carbon nanotubes, attracting the attention of scientists. At present, there are two main ways to construct chiral macrocycles: one is to introduce achiral units, destroying the high symmetry of macrocycles by steric hindrance to construct inherent chirality; the other is to introduce chiral units directly. For many reported chiral macrocycles, building units are introduced before the aromatization reaction of CPP macrocycles. Herein, we design a new chiral macrocycle based on CPPs structures. We select the classical methoxy-modified cyclohexadiene units as precursors, introducing the thiophene 1,1-dioxide into the CPP skeleton. Then we try to introduce chiral units through Diels-Alder post-modification reaction, in order to synthesizing the macrocycle with N-R* phthalimide backbone. The research can facilitate the synthesis of macrocycles with various chiral groups and provide alternative materials and new ideas for the following research.

参考文献总数:

 39    

插图总数:

 25    

插表总数:

 0    

馆藏号:

 本070301/23112    

开放日期:

 2024-06-04    

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