Tetrylenes based on 1,10-phenanthroline-containing diol: the synthesis and application as initiators of ε-caprolactone polymerization
- Authors: Mankaev B.N.1,2, Zaitsev K.V.1,2, Timashova V.S.1,2, Zaitseva G.S.1,2, Egorov M.P.1, Karlov S.S.1,2
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Affiliations:
- Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Department of Chemistry, Lomonosov Moscow State University
- Issue: Vol 67, No 3 (2018)
- Pages: 542-547
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/242376
- DOI: https://doi.org/10.1007/s11172-018-2108-5
- ID: 242376
Cite item
Abstract
Treatment of 4,7-dichloro-2,9-dimethyl-1,10-phenanthroline with two equivalents of p-tert-butylphenol in the presence of К2СО3 afforded 4,7-di(4-tert-butylphenoxy)-2,9-dimethyl-1,10-phenanthroline (1). Monolithiation of 1 with lithium diisopropylamide followed by treatment with benzophenone resulted in 1-(4,7-bis-p-tert-butylphenoxy-9-methyl-1,10- phenanthrolin-2-yl)methyl-1,1-diphenylethanol (2). 1-(4,7-Bis-p-tert-butylphenoxy-9-hydroxy (diphenyl)methyl-1,10-phenanthrolin-2-yl)-1,1-diphenylethanol (3), a tetradentate ONNO ligand, was prepared analogously from 2. The interaction of 3 with 1 eq. of Lappert’s germylene or stannylene M[N(SiMe3)2]2 (M = Ge, Sn) led to the corresponding germylene 4 and stannylene 5 in moderate yields. According to 1Н, 13С, and 119Sn NMR spectroscopy data, stannylene 5 is monomeric in solution and the coordination number of tin atom is 4. Tetrylenes 4 and 5 demonstrated high activity as initiators of bulk polymerization of ε-caprolactone which leads to high-molecular-weight polymers with relatively narrow molecular weight distribution.
About the authors
B. N. Mankaev
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Department of Chemistry, Lomonosov Moscow State University
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 3 Build., 1 Leninskie Gory, Moscow, 119991
K. V. Zaitsev
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Department of Chemistry, Lomonosov Moscow State University
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 3 Build., 1 Leninskie Gory, Moscow, 119991
V. S. Timashova
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Department of Chemistry, Lomonosov Moscow State University
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 3 Build., 1 Leninskie Gory, Moscow, 119991
G. S. Zaitseva
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Department of Chemistry, Lomonosov Moscow State University
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 3 Build., 1 Leninskie Gory, Moscow, 119991
M. P. Egorov
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
S. S. Karlov
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences; Department of Chemistry, Lomonosov Moscow State University
Author for correspondence.
Email: sergej@org.chem.msu.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991; 3 Build., 1 Leninskie Gory, Moscow, 119991