Synthesis of cyclo- and polyphosphazenes with pyridine side groups

Ursula Diefenbach, Harry R. Allcock

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

New types of cyclo- and polyphosphazenes that bear pyridine side groups have been synthesized. The reactions of 2-(2-aminoethyl)pyridine and 2-((2-aminoethyl)amino)-5-nitropyridine with (NPCl2)3 were complex, with chlorine replacement being complicated by degradation and the formation of mixtures. However, the use of electron withdrawing cosubstituents, such as phenoxy or trifluoroethoxy groups, allows straightforward chlorine replacement reactions induced by the aminoalkylpyridines to occur. The mono(alkylpyridine)-substituted cyclotriphosphazenes N3P3(OC6H5)5(NHCH 2CH2(C5H4N)) (1) and N3P3(OC6H5)5(NHCH 2CH2NH(C5H3N)NO2) (2) were synthesized as model compounds for high polymers. Polyphosphazenes of the general formula [NP(OCH2CF3)x(NHCH2- CH2(C5H4N))y]n were prepared by exposing [NPCl2]n to sodium trifluorethoxide and 2-(2-aminoethyl)pyridine in a two-step reaction. All compounds were characterized by 1H, 13C, 31P NMR spectroscopy, and elemental analysis. The cyclic trimers were also identified by mass spectrometry. Molecular weight estimations of the polymers were carried out by gel permation chromatography, and glass transition temperatures were determined by differential scanning calorimetry.

Original languageEnglish (US)
Pages (from-to)4562-4565
Number of pages4
JournalInorganic Chemistry
Volume33
Issue number20
StatePublished - 1994

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Chlorine
pyridines
Polymers
chlorine
synthesis
Chromatography
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Differential scanning calorimetry
high polymers
gel chromatography
Gels
Sodium
Molecular weight
trimers
bears
Degradation
glass transition temperature
Electrons
molecular weight

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

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title = "Synthesis of cyclo- and polyphosphazenes with pyridine side groups",
abstract = "New types of cyclo- and polyphosphazenes that bear pyridine side groups have been synthesized. The reactions of 2-(2-aminoethyl)pyridine and 2-((2-aminoethyl)amino)-5-nitropyridine with (NPCl2)3 were complex, with chlorine replacement being complicated by degradation and the formation of mixtures. However, the use of electron withdrawing cosubstituents, such as phenoxy or trifluoroethoxy groups, allows straightforward chlorine replacement reactions induced by the aminoalkylpyridines to occur. The mono(alkylpyridine)-substituted cyclotriphosphazenes N3P3(OC6H5)5(NHCH 2CH2(C5H4N)) (1) and N3P3(OC6H5)5(NHCH 2CH2NH(C5H3N)NO2) (2) were synthesized as model compounds for high polymers. Polyphosphazenes of the general formula [NP(OCH2CF3)x(NHCH2- CH2(C5H4N))y]n were prepared by exposing [NPCl2]n to sodium trifluorethoxide and 2-(2-aminoethyl)pyridine in a two-step reaction. All compounds were characterized by 1H, 13C, 31P NMR spectroscopy, and elemental analysis. The cyclic trimers were also identified by mass spectrometry. Molecular weight estimations of the polymers were carried out by gel permation chromatography, and glass transition temperatures were determined by differential scanning calorimetry.",
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Synthesis of cyclo- and polyphosphazenes with pyridine side groups. / Diefenbach, Ursula; Allcock, Harry R.

In: Inorganic Chemistry, Vol. 33, No. 20, 1994, p. 4562-4565.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of cyclo- and polyphosphazenes with pyridine side groups

AU - Diefenbach, Ursula

AU - Allcock, Harry R.

PY - 1994

Y1 - 1994

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AB - New types of cyclo- and polyphosphazenes that bear pyridine side groups have been synthesized. The reactions of 2-(2-aminoethyl)pyridine and 2-((2-aminoethyl)amino)-5-nitropyridine with (NPCl2)3 were complex, with chlorine replacement being complicated by degradation and the formation of mixtures. However, the use of electron withdrawing cosubstituents, such as phenoxy or trifluoroethoxy groups, allows straightforward chlorine replacement reactions induced by the aminoalkylpyridines to occur. The mono(alkylpyridine)-substituted cyclotriphosphazenes N3P3(OC6H5)5(NHCH 2CH2(C5H4N)) (1) and N3P3(OC6H5)5(NHCH 2CH2NH(C5H3N)NO2) (2) were synthesized as model compounds for high polymers. Polyphosphazenes of the general formula [NP(OCH2CF3)x(NHCH2- CH2(C5H4N))y]n were prepared by exposing [NPCl2]n to sodium trifluorethoxide and 2-(2-aminoethyl)pyridine in a two-step reaction. All compounds were characterized by 1H, 13C, 31P NMR spectroscopy, and elemental analysis. The cyclic trimers were also identified by mass spectrometry. Molecular weight estimations of the polymers were carried out by gel permation chromatography, and glass transition temperatures were determined by differential scanning calorimetry.

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