Tetrylenes based on 1,10-phenanthroline-containing diol: the synthesis and application as initiators of ε-caprolactone polymerization

Journal Article · Thu Mar 15 04:00:00 EDT 2018 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-018-2108-5· OSTI ID:22863355

Mankaev, B. N.; Zaitsev, K. V.; Timashova, V. S.; Zaitseva, G. S.; Egorov, M. P.

Treatment of 4,7-dichloro-2,9-dimethyl-1,10-phenanthroline with two equivalents of p-tert-butylphenol in the presence of К{sub 2}СО{sub 3} 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(SiMe{sub 3}){sub 2}]{sub 2} (M = Ge, Sn) led to the corresponding germylene 4 and stannylene 5 in moderate yields. According to {sup 1}Н, {sup 13}С, and {sup 119}Sn 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.

• OSTI ID: 22863355
• Journal Information: Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 3 Vol. 67; ISSN RCBUEY; ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
BENZOPHENONE
CARBON 13
COORDINATION NUMBER
GERMANIUM COMPOUNDS
GLYCOLS
HYDROGEN 1
LIGANDS
LITHIUM COMPOUNDS
MOLECULAR WEIGHT
NUCLEAR MAGNETIC RESONANCE
PHENANTHROLINES
POLYMERIZATION
POLYMERS
SOLUTIONS
SPECTROSCOPY
SYNTHESIS
TIN
TIN 119