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[1]朱正钟,李姝慧,陈佐长,等.1,3,5,7,9-五咔唑基心环烯的合成与表征[J].厦门大学学报(自然科学版),2019,58(04):485-490.[doi:10.6043/j.issn.0438-0479.201810018]
 ZHU Zhengzhong,LI Shuhui,CHEN Zuochang,et al.Synthesis and characterization of 1,3,5,7,9-pentacarbazolylcorannulene[J].Journal of Xiamen University(Natural Science),2019,58(04):485-490.[doi:10.6043/j.issn.0438-0479.201810018]
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《厦门大学学报(自然科学版)》[ISSN:0438-0479/CN:35-1070/N]

卷:
58卷
期数:
2019年04期
页码:
485-490
栏目:
研究论文
出版日期:
2019-07-28

文章信息/Info

Title:
Synthesis and characterization of 1,3,5,7,9-pentacarbazolylcorannulene
文章编号:
0438-0479(2019)04-0485-06
作者:
朱正钟李姝慧陈佐长徐云彦张前炎谢素原*黄荣彬郑兰荪
厦门大学化学化工学院,固体表面物理化学国家重点实验室,福建 厦门 361005
Author(s):
ZHU ZhengzhongLI ShuhuiCHEN ZuochangXU YunyanZHANG QianyanXIE Suyuan*HUANG RongbinZHENG Lansun
State Key Laboratory of Physical Chemistry of Solid Surfaces,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China
关键词:
心环烯 咔唑 13579-五咔唑基心环烯 亲核取代反应
Keywords:
corannulene carbazole 13579-pentacarbazolylcorannulene nucleophilic substitution reaction
分类号:
O 613.42; O 613.71
DOI:
10.6043/j.issn.0438-0479.201810018
文献标志码:
A
摘要:
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.
Abstract:
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.

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备注/Memo

备注/Memo:
收稿日期:2018-10-22录用日期:2018-11-27
基金项目:国家自然科学基金(21771152,21721001,21390390,51572231,21701134); 福建省科技厅高校产学合作项目(2016H6023); 中央高校基本科研业务费专项(20720170028,20720160084)
*通信作者:syxie@xmu.edu.cn
更新日期/Last Update: 1900-01-01