《厦门大学学报（自然科学版）》

自从作为富勒烯片段的心环烯分子被合成以来,大量具有C5对称性的碳—碳、碳—卤、碳—硼、碳—氧和碳—硫键修饰的心环烯衍生物陆续被合成,然而具有C5对称性的碳—氮键修饰的心环烯衍生物至今还没有报道.该研究通过五咔唑氮负离子对1,3,5,7,9-五氯心环烯的亲核取代反应实现了碳—氮键偶联,并得到具有C5对称性的心环烯衍生物1,3,5,7,9-五咔唑基心环烯.采用核磁共振波谱和高分辨质谱进行表征证实其具有C5对称结构,并采用密度泛函理论(DFT)计算模拟了其立体结构.作为一类富电子的含氮杂环,咔唑基团及其衍生物表现出许多优异的光电性能和生物活性,因此1,3,5,7,9-五咔唑基心环烯分子的成功合成不仅提供了一类新型的碳—氮键修饰的心环烯衍生物,而且该分子可能在超分子自组装、光电材料、生物方面具有重要的潜在应用价值.

Since the synthesis of corannulene, a subunit of fullerene, a large number of C5-symmetric carbon-carbon,carbon-halogen,carbon-boron,carbon-oxygen and carbon-sulfur bond-modified corannulene derivatives have been successively synthesized.However, a carbon-nitrogen bond-modified corannulene derivative has not been reported so far.In this work,a C5-symmetric corannulene derivative 1,3,5,7,9-pentacarbazolylcorannulene was synthesized through a carbon-nitrogen bond coupling reaction and a nucleophilic substitution reaction of carbazole nitrogen anion to 1,3,5,7,9-pentachlorocorannulene.The C5-symmetric molecular structure was confirmed using nulcear magnetic resonance spectroscopy and high resolution mass spectrometry.The spatial structure was calculated based on density functional theory(DFT).As a class of electron-rich nitrogen heterocycles,carbazole and its derivatives exhibited excellent photoelectric properties and biological activities.Therefore, the successful synthesis of the 1,3,5,7,9-pentacarbazolylcorannulene provides a new class of carbon-nitrogen bond-modified corannulene derivatives, which may show important potential application value in supramolecular self-assembly,optoelectronic materials and biological aspects.

引言
1 实验部分
2 结果与讨论
3 结论

图1 1,3,5,7,9-五取代心环烯衍生物的代表性例子<br/>Fig.1 Examples of 1,3,5,7,9-penta-substituted corannulene derivatives

图1 1,3,5,7,9-五取代心环烯衍生物的代表性例子
Fig.1 Examples of 1,3,5,7,9-penta-substituted corannulene derivatives

图2 1,3,5,7,9-五咔唑基心环烯(8)的合成路线<br/>Fig.2 Synthetic route for 1,3,5,7,9-pentacarbazolylcorannulene(8)

图2 1,3,5,7,9-五咔唑基心环烯(8)的合成路线
Fig.2 Synthetic route for 1,3,5,7,9-pentacarbazolylcorannulene(8)

图3 化合物8的1H-NMR(a)和13C-NMR(b)谱图<br/>Fig.3 1H-NMR(a)and 13C-NMR(b)spectra of compound 8

图3 化合物8的1H-NMR(a)和13C-NMR(b)谱图
Fig.3 1H-NMR(a)and 13C-NMR(b)spectra of compound 8

图4 化合物8的液态(a)和固态(b)紫外-可见吸收光谱<br/>Fig.4 Liquid(a)and solid(b)UV-Vis absorption spectra of compound 8

图4 化合物8的液态(a)和固态(b)紫外-可见吸收光谱
Fig.4 Liquid(a)and solid(b)UV-Vis absorption spectra of compound 8

图5 1,3,5,7,9-五咔唑基心环烯分子的理论计算结构及轨道<br/>Fig.5 Calculated molecular structure and orbital of 1,3,5,7,9-pentacarbazolylcorannulene

图5 1,3,5,7,9-五咔唑基心环烯分子的理论计算结构及轨道
Fig.5 Calculated molecular structure and orbital of 1,3,5,7,9-pentacarbazolylcorannulene

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备注

引言

1 实验部分

2 结果与讨论

3 结论

学报简介

备注

引言

1 实验部分

2 结果与讨论

3 结 论

学报简介

3 结论