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| 基于联苯构建多环芳烃的合成与表征 |
| Synthesis and characterization of polycyclic aromatic hydrocarbons based on biphenyls |
| 投稿时间：2024-03-26 修订日期：2024-05-09 |
| DOI： |
| 中文关键词: 多环芳烃 庚搭烯结构 联苯结构 |
| 英文关键词: Polycyclic aromatic hydrocarbons Heptadiene structure biphenyl structure |
| 基金项目:国家自然科学基金项目（面上项目，重点项目，重大项目）,湖南省重点研发项目，湖南省杰出青年基金，新型有机光电磁性碳材料，湖湘高层次人才聚集工程-创新人才 |
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| 中文摘要: |
| 多环芳烃一直是科学家们研究的热点,其中庚搭烯结构的多环芳烃更是其中一个有趣的体系,由于其高反应活性而导致其制备与表征极具挑战,本文设计了一类基于联苯具有庚搭烯结构的多环芳烃,拟通过区域性溴代、亲核取代、格氏反应、分子内关环、脱氢氧化等反应得到目标产物。然而,在分子内关环时,分子发生重排,得到重排产物：4-(1H-茚-3-基)-9H-芴(Y-1),结构用X-射线单晶衍射进行了确认。对Y-1的重排原因进行了分析,提出了重排机理,并通过紫外吸收光谱和电化学对Y-1的光电性质进行分析。该分子的重排反应将有助于我们对于分子内关环策略的理解。 |
| 英文摘要: |
| Polycyclic aromatic hydrocarbons (PAHs) have always been the focus of research by scientists, among which the PAHs with heptaene structure are one of the interesting systems. Due to their high reactivity, their preparation and characterization are very challenging. In this paper, a class of PAHs with heptaene structure based on biphenyl is designed. The target product is obtained by regional bromination, nucleophilic substitution, grignard reaction, intramolecular ring closure, dehydrogenation and other reactions. However, the molecular rearrangement occurred during intramolecular closure, and the rearrangement product was 4- (1h-indene-3-yl) -9h-fluorene (Y-1). The structure was confirmed by single crystal X-ray diffraction. The reason of Y-1 rearrangement was analyzed, the mechanism of rearrangement was proposed, and the photoelectric properties of Y-1 were analyzed by UV absorption spectrum and electrochemistry. This molecular rearrangement will contribute to our understanding of intramolecular loop closure strategies. |
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