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Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-09-09 , DOI: 10.3762/bjoc.16.186
Shakeel Alvi , Rashid Ali

Since the first synthetic report in 2003 by Sakurai et al., sumanene (derived from the Indian ‘Hindi as well as Sanskrit word’ “Suman”, which means “Sunflower”), a beautifully simple yet much effective bowl-shaped C3-symmetric polycyclic aromatic hydrocarbon having three benzylic positions clipped between three phenyl rings in the triphenylene framework has attracted a tremendous attention of researchers worldwide. Therefore, since its first successful synthesis, a variety of functionalized sumanenes as well as heterosumanenes have been developed because of their unique physiochemical properties. For example, bowl-to-bowl inversion, bowl depth, facial selectivity, crystal packing, metal complexes, intermolecular charge transfer systems, cation–π complexation, electron conductivity, optical properties and so on. Keeping the importance of this beautiful scaffold in mind, we compiled all the synthetic routes available for the construction of sumanene and its heteroatom derivatives including Mehta’s first unsuccessful effort up to the latest achievements. Our major goal to write this review article was to provide a quick summary of where the field has been, where it stands at present, and where it might be going in near future. Although several reviews have been published on sumanene chemistry dealing with different aspects but this is the first report that comprehensively describes the ‘all-in-one’ chemistry of the sumanene architecture since its invention to till date. We feel that this attractive review article will definitely help the scientific community working not only in the area of organic synthesis but also in materials science and technology.

中文翻译:

碗状π共轭苏南烯及其同类物的合成方法

自Sakurai等人于2003年首次发表综合报告以来,sumanene(源自印度的“印地语”和梵语“ Suman”,意为“向日葵”),是一种精美而有效的碗形C 3在三亚苯基骨架中的三个苯环之间夹有三个苄基的不对称多环芳烃引起了全世界研究者的极大关注。因此,自其首次成功合成以来,由于其独特的理化性质,已开发出多种功能化的苏烷以及杂sum烷。例如,碗对碗的倒置,碗深度,面部选择性,晶体堆积,金属络合物,分子间电荷转移系统,阳离子-π络合物,电子电导率,光学性质等。牢记这个美丽的支架的重要性,我们汇总了可用于构建苏南烯及其杂原子衍生物的所有合成路线,包括Mehta的首次失败努力直至最新成就。我们写这篇评论文章的主要目的是提供一个简短的摘要,说明该领域的现状,当前的现状以及不久的将来。尽管已经发表了有关舒马烯化学的不同方面的一些评论,但是这是自迄今为止发明以来,第一份全面描述舒马烯结构的“多合一”化学的报告。我们认为这篇引人入胜的评论文章必将帮助科学界不仅在有机合成领域而且在材料科学和技术领域开展工作。尽管已经发表了有关舒马烯化学的不同方面的一些评论,但是这是自迄今为止发明以来,第一份全面描述舒马烯结构的“多合一”化学的报告。我们认为这篇引人入胜的评论文章必将帮助科学界不仅在有机合成领域而且在材料科学和技术领域开展工作。尽管已经发表了有关舒马烯化学的不同方面的一些评论,但是这是自迄今为止发明以来,第一份全面描述舒马烯结构的“多合一”化学的报告。我们认为这篇引人入胜的评论文章必将帮助科学界不仅在有机合成领域而且在材料科学和技术领域开展工作。
更新日期:2020-09-10
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