TY - JOUR
T1 - 二胺与二酮环聚合反应的不同途径与产物
AU - Zhu, Lei
AU - Han, Junyan
AU - Chang, Haizhen
AU - Qiu, Yuyuan
AU - Zhang, Yanan
AU - Peng, Danni
AU - Hu, Wei
AU - Miao, Shaobin
N1 - Funding Information:
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.
Publisher Copyright:
© 2018, Higher Education Press. All right reserved.
Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.
PY - 2018/12/1
Y1 - 2018/12/1
N2 - 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.
AB - 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.
KW - Azacene
KW - Cyclo-condensation reaction
KW - Organic semiconductor
KW - Ring expansion
KW - Single-crystal structure
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U2 - 10.7503/cjcu20180302
DO - 10.7503/cjcu20180302
M3 - Article
AN - SCOPUS:85061741705
SN - 0251-0790
VL - 39
SP - 2686
EP - 2692
JO - Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities
JF - Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities
IS - 12
ER -