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化学学报
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化学学报 ›› 2012, Vol. 70 ›› Issue (17): 1791-1797.DOI: 10.6023/A12050262 上一篇    下一篇

研究论文

手性酞菁的合成及其绝对构型

王康a, 王海龙a, 约翰·马克b, 李文军a, 小林长夫b, 姜建壮a   

  1. a 北京科技大学化学与生物工程学院 功能分子与晶态材料科学与应用北京市重点实验室 北京 100083;
    b 日本东北大学理学院化学系 仙台 980-8578
  • 投稿日期:2012-05-31 发布日期:2012-07-18
  • 通讯作者: 小林长夫, 姜建壮
  • 基金资助:

    项目受国家自然科学基金(No. 2012CB224801)、教育部重点学校基础研究基金、北京市教育委员会和日本教育部科学创新基金(No. 20108007)及科学研究基金(B)(No. 23350095)的资助.

Chiral Phthalocyanine with Unambiguous Absolute Molecular Structures for Both Enantiomers

Wang Kanga, Wang Hailonga, Mack Johnb, Li Wenjuna, Kobayashi Nagaob, Jiang Jianzhuanga   

  1. a Beijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, China;
    b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
  • Received:2012-05-31 Published:2012-07-18
  • Supported by:

    Project supported by the National Natural Science Foundation of China, the National Ministry of Science and Technology of China (No. 2012CB224801), Fundamental Research Funds for the Central universities of Ministry of Education of China, Beijing Municipal Commission of Education, Grant-in-Aid for Scientific Research on Innovative areas (No. 20108007, “pi-Space”), Scientific Research (B) (No. 23350095).

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被引次数

8

在锂存在的条件下在正戊醇中回流环化四聚相应的光学活性的前驱体联二萘[2,1-e:1',2'-g][1,4]二羟基-5,6-邻苯二氰, 然后用醋酸酸化处理, 合成了一对对映的四个联二萘酚基团取代的手性自由酞菁四(联二萘[1,2-e:1',2'-g]-1,4-二羟基)[2,3-b;2',3'-k;2'',3''-t;2''',3'''-c']酞菁(1), 并利用一系列的光谱学方法以及元素分析表征了这种新型的手性酞菁化合物. 单晶X衍射分析确定了两种对映体的绝对构型, 从而阐明了自由酞菁(1)的手性分配.

关键词: 酞菁, 手性, 光学活性, 绝对构型, 单晶X衍射分析

(R)- and (S)-Enantiomers of chiral metal free tetrakis(dinaphtho[1,2-e:1',2'-g]-1,4-dioxocine)-[2,3-b;2',3'-k;2'',3''-t; 2''',3'''-c']phthalocyanine (1) were synthesized via a cyclic tetramerization of the corresponding optically active benzo[b]dinaphtho[2,1-e:1',2'-g][1,4]dioxocine-5,6-dicarbonitrile (2) in refluxing n-pentanol in the presence of lithium followed by treatment with acetic acid. This novel chiral phthalocyanine compound has been characterized by a series of spectroscopic methods in addition to elemental analysis. The absolute molecular structures of both enantiomers have been unambiguously elucidated by single crystal X-ray diffraction analysis, resulting in the direct assignment of the chirality of metal free phthalocyanine 1.

Key words: phthalocyanine, chiral, optically active, absolute molecular structure, single crystal X-ray diffraction analysis