高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (12): 2686-2692.doi: 10.7503/cjcu20180302

• 有机化学 • 上一篇    下一篇

二胺与二酮环聚合反应的不同途径与产物

朱磊1, 韩军燕1, 常海珍1, 邱宇渊1, 张雅楠1, 彭丹妮1, 胡伟2(), MiaoShaobin3()   

  1. 1. 湖南大学化学化工学院
    2. 物理与微电子科学学院, 长沙 410082
    3. 奥古斯塔大学化学与物理系, 奥古斯塔 30912, 美国
  • 收稿日期:2018-04-17 出版日期:2018-11-16 发布日期:2018-11-16
  • 作者简介:

    联系人简介: 胡 伟, 男, 博士, 助理教授, 主要从事半导体光电子器件领域的研究. E-mail: huwei@hnu.edu.cn;Miao Shaobin, 男, 博士, 副教授, 主要从事有机半导体领域的研究. E-mail: smiao@augusta.edu

  • 基金资助:
    国家自然科学基金(批准号: 21271070)、 湖南省自然科学基金(批准号: 2016JJ2028)及奥古斯塔大学化学与物理系资助.

Different Pathways for the Cyclocondensation Reactions of 1,2-Diamine and 1,2-Diketone

ZHU Lei1, HAN Junyan1, CHANG Haizhen1, QIU Yuyuan1, ZHANG Yanan1, PENG Danni1, HU Wei2,*(), MIAO Shaobin3,*()   

  1. 1. College of Chemistry and Chemical Engineering
    2. School of Physics and Electronics, Hunan University, Changsha 410082, China
    3. Department of Chemistry and Physics, Augusta University, Augusta 30912, USA
  • Received:2018-04-17 Online:2018-11-16 Published:2018-11-16
  • Contact: HU Wei,MIAO Shaobin E-mail:huwei@hnu.edu.cn;smiao@augusta.edu
  • Supported by:
    † Supported by the National Natural Science Foundation of China(No.21271070) , the Natural Science Foundation of Hunan Province, China(No.2016JJ2028) and the Department of Chemistry and Physics at Augusta University.

摘要:

在质子性溶剂中, 3,5-二叔丁基-1,2-苯醌分别与双[(三异丙基硅烷基)乙炔基]萘-2,3-二胺和双[(三异丙基硅烷基)乙炔基]蒽-2,3-二胺反应, 在不同条件下得到含有吡嗪环的缩合产物1和含有咪唑环的缩合产物2. 通过核磁共振波谱、 紫外-可见光谱、 高分辨质谱及单晶X射线衍射表征确定了产物的结构, 并提出了可能的反应机理.

关键词: 氮杂并苯, 缩合成环反应, 增环反应, 有机半导体, 单晶结构

Abstract:

It is generally acknowledged that in protic organic solvents, 1,2-diamine reacts with 1,2-diketone to form an aromatic compound containing the pyrazine ring. As expected, the condensation reactions of 1,4-bis-[(triisopropylsilyl)ethynyl]naphthalene-2,3-diamine or 1,4-bis[(triisopropylsilyl)ethynyl]anthracene-2,3-diamine with 3,5-di-tert-butyl-1,2-benzoquinone yielded diazatetracene and diazapentacene derivatives. Meanwhile, naphthoazepin and anthroazepin derivatives which contained the imidazole ring were also obtained. Naphthoazepin and anthroazepin derivatives contained a seven-membered ring. All new compounds were characterized by proton and carbon-13 nuclear magnetic resonance spectroscopy, UV-vis spectrophotometry, high resolution mass spectrometry and single crystal X-ray diffraction. The possible reaction mechanisms were proposed as well.

Key words: Azacene, Cyclo-condensation reaction, Ring expansion, Organic semiconductor, Single-crystal structure

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