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中文题名:

 基于[5]螺烯和环对苯撑结构的[4n]莫比乌斯共轭全碳纳米环:合成、拓扑以及莫比乌斯芳香性    

姓名:

 杨惠吉    

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:

 [4n]Möbius Conjugated All-carbon Nanohoops By Hybridization of [5]helicene and Cycloparaphenylene Units: Synthesis, Topology and Möbius Aromaticity    

中文关键词:

 莫比乌斯拓扑 ; 芳香性 ; 碳纳米环 ; [5]螺烯 ; 圆偏振发光    

外文关键词:

 Möbius topology ; aromaticity ; nanohoop ; [5]helicene ; circularly polarized luminescence    

中文摘要:

具有莫比乌斯拓扑结构的全碳共轭纳米大环对于理解莫比乌斯芳香性和拓扑手性至关重要。然而,由于[4n]共轭莫比乌斯环产生强应变,使得该类合成较为困难。在本论文中,我们利用[5]螺烯隐性的扭曲和掩蔽芳环单元来克服莫比乌斯拓扑结构带来的应变,合成了单扭曲的[4n]莫比乌斯共轭全碳纳米环([5]H-[7, 8]CPPs)。X射线分析表明,[5]H-[7, 8]CPPs含有[5]螺烯部分和对苯撑单元,并显示出单扭曲莫比乌斯拓扑结构。光物理研究表明,相比于[5]螺烯和[7,8]CPPs,[5]H-[7, 8]CPPs表现出更高的荧光量子产率。手性光物理学研究表明,[5]H-[7, 8]CPPs在圆二色谱和圆偏振光谱中表现出明显的科顿效应,表明化合物具有手性,即[5]螺烯的手性有效地转移到整个大环上。理论计算表明,这种全碳纳米环是具有莫比乌斯芳香性的全共轭体系。

外文摘要:

Conjugated all-carbon nanohoops with a Möbius topology is essential for understanding Möbius aromaticity and topological chirality. However, the synthesis of Möbius aromatic all-carbon nanohoops is inherently difficult because of the challenges associated with the strong strain in an overall conjugated 4n π-electron Möbius annulene. In this work, we reported the synthesis of [4n]Möbius conjugated all-carbon nanohoops ([5]H-[7,8]CPPs) by using the [5]helicene unit as a hidden writhe and masking aromatic ring units to overcome the strain imposed by the Möbius topology. X-ray analysis revealed that [5]H-[7, 8]CPPs contain a [5]helicene moiety and an oligoparaphenylene unit, and display a Möbius topology. Photophysical investigations demonstrated that [5]H-[7, 8]CPPs exhibited moderately high fluorescence quantum yields, which are significantly higher than those of pristine [5]helicene and [7, 8]CPPs. Chiroptical studies revealed that [5]H-[7, 8]CPPs displayed an obvious Cotton effect in circular dichroism and bright circularly polarized luminescence, indicating that the compounds are chiral, which means the chirality of [5] helicene is effectively transferred to the whole macrocycle. Theoretical investigations reveal that such all-carbon nanohoops are fully conjugated systems with Möbius aromaticity.

参考文献总数:

 39    

优秀论文:

 北京市高校优秀本科毕业论文    

作者简介:

 杨惠吉,内蒙古自治区鄂尔多斯人,2019年进入北京师范大学化学学院学习,在江华教授的指导下进行拓扑手性共轭大环的研究工作。    

插图总数:

 61    

插表总数:

 17    

馆藏号:

 本070301/23055    

开放日期:

 2024-06-04    

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