二胺与二酮环聚合反应的不同途径与产物

Translated title of the contribution: Different Pathways for the Cyclocondensation Reactions of 1,2-Diamine and 1,2-Diketone

Lei Zhu, Junyan Han, Haizhen Chang, Yuyuan Qiu, Yanan Zhang, Danni Peng, Wei Hu, Shaobin Miao

Research output: Contribution to journalArticle

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.

Original languageChinese
Pages (from-to)2686-2692
Number of pages7
JournalGaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities
Volume39
Issue number12
DOIs
StatePublished - Dec 1 2018

Fingerprint

Diamines
Derivatives
Pyrazines
Condensation reactions
Aromatic compounds
Spectrophotometry
Organic solvents
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Protons
Carbon
Single crystals
X ray diffraction

Keywords

  • Azacene
  • Cyclo-condensation reaction
  • Organic semiconductor
  • Ring expansion
  • Single-crystal structure

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

二胺与二酮环聚合反应的不同途径与产物. / Zhu, Lei; Han, Junyan; Chang, Haizhen; Qiu, Yuyuan; Zhang, Yanan; Peng, Danni; Hu, Wei; Miao, Shaobin.

In: Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities, Vol. 39, No. 12, 01.12.2018, p. 2686-2692.

Research output: Contribution to journalArticle

Zhu, Lei ; Han, Junyan ; Chang, Haizhen ; Qiu, Yuyuan ; Zhang, Yanan ; Peng, Danni ; Hu, Wei ; Miao, Shaobin. / 二胺与二酮环聚合反应的不同途径与产物. In: Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities. 2018 ; Vol. 39, No. 12. pp. 2686-2692.
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