Laser Desorption Ionization of Arylene Phenylphosphonites Formed by Condensation of Dihydric Phenols with Phenylphosphonous Bis(diethylamide)

Teleshev, A. T.; Maksimov, B. I.; Mishina, V. Yu.; Abrashina, I. V.; Grinberg, V. Ya.; Нифантьев, Э. Е.

doi:10.1007/s11176-005-0432-6

Cited by 5 publications

(5 citation statements)

References 5 publications

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“…In spite of the potential difficulties described above, the

{\overset{M}{true}}_{n}

s determined by SEC are in good agreement with those calculated from the 31 P{ 1 H} NMR integrations, with all values being greater than 10 4 Da (Table ). These molecular weights are of the same order of magnitude as reported for poly(H‐phosphonates) and are an order of magnitude greater than those reported for the similar poly(arylene phenylphosphonates) . The good agreement between

{\overset{M}{true}}_{n}

s determined by the two methods suggests that the polyphosphonates are primarily linear chains with essentially no cyclic oligomers present.…”

Section: Resultssupporting

confidence: 65%

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Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Freeman

Martin

Totsch

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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The syntheses of a series of substituted polyphosphonates of the type [OP(X)(Ar)O(CH2)12]n (X = O, S, Se; Ar = phenyl, 2,2′‐bithienyl‐5‐yl) are reported. The trueM¯ns for the polyphosphonates range from 1.1 to 4.6 × 104 Da and are significantly higher than those previously reported for polyphosphonates synthesized via polycondensation reactions. Thermal characterization indicates that all of the polymers are in the rubbery state at room temperature and have thermal stabilities as high as 290 °C. The linear absorption spectra, emission spectra, and emission quantum yields of the 2,2′‐bithenyl‐5‐yl substituted polyphosphonates show distinct trends with respect to the chalcogen attached to the phosphorus. Solutions of these polymers show emission at wavelengths ranging from 380 to 400 nm and, depending on the choice of X, the quantum yields are considerably larger than that of 2,2′‐bithiophene. Nonlinear optical measurements of the polyphosphonates with 2,2′‐bithenyl‐5‐yl substituents show that nonlinear absorbance increases with increasing molecular weight of X. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3663–3674

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“…In spite of the potential difficulties described above, the

{\overset{M}{true}}_{n}

{\overset{M}{true}}_{n}

s determined by the two methods suggests that the polyphosphonates are primarily linear chains with essentially no cyclic oligomers present.…”

Section: Resultssupporting

confidence: 65%

“…However, Nifant'ev et al . have reported that attempts to synthesize poly(phenylphosphonites) (Chart ; R = Ph, R′ = arylene, X = ··) using either this method or a slightly modified sonochemical method gave relatively low molecular weights of 6 − 9 kDa presumably due to side reactions that terminated the polymerization …”

Section: Introductionmentioning

confidence: 99%

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Freeman

Martin

Totsch

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…This behavior suggested that BDM was heat sensitive. This result is similar to those of Nifant'ev et al in which thermal decomposition of a polyphosphonite derived from bisphenol‐A, which has a higher melting point than does 1,4‐benzenediemethanol, 19,20 was observed. To avoid thermal decomposition of the BDM polymers, the reactions conditions were altered to minimize exposure to high temperatures.…”

Section: Resultssupporting

confidence: 90%

“…We previously reported that polyphosphonates with moderately high molecular weights could be prepared by the polycondensations of 1,12‐dodecanediol with bis(diethylamino)arylphosphines (aryl=phenyl, 2,2′‐bithiophenyl) followed by oxidation with a chalcogen 21 . While this result was extremely promising for the synthesis of these highly modular polymers, some literature suggested that the polycondensation might not work with all diols 19,20 …”

Section: Discussionmentioning

confidence: 99%

“…Nifant'ev et al was able to prepare polyphosphonites, a P(III) analog of polyphosphonates in which the lone pair on the phosphorus remains available for reaction, through a polycondensation reaction between bis(diethylamino)phenylphosphine (P(Ph)(NEt 2 ) 2 ) and an organic diol 19,20 . Unfortunately, higher molecular weight polymers (≥1 × 10 4 Da) could not be prepared without significant side product formation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of modular polyphosphonate homopolymers and copolymers

Totsch

Stanford

Klep

et al. 2020

Journal of Polymer Science

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Linear polyphosphonates with the generic formula –[P(Ph)(X)OR′O]n– (X = S or Se) have been synthesized by polycondensations of P(Ph)(NEt2)2 and a diol (HOR′OH = 1,4‐cyclohexanedimethanol, 1,4‐benzenedimethanol, tetraethylene glycol, or 1,12‐dodecanediol) followed by reaction with a chalcogen. Random copolymers have been synthesized by polycondensations of P(Ph)(NEt2)2 and mixture of two of the diols in a 2:1:1 mol ratio followed by reaction with a chalcogen. Block copolymers with the generic formula –[P(Ph)(X)OR′O](x + 2) –[P(Ph)(X)OR′O](x + 3)– (X = S or Se) have been synthesized by the polycondensations of Et2N[P(Ph)(X)OR′O](x + 2)P(Ph)NEt2 oligomers with HOR′O[P(Ph)(X)OR′O](x + 3)H oligomers followed by reaction with a chalcogen. The Et2N[P(Ph)(X)OR′O](x + 2)P(Ph)NEt2 oligomers are prepared by the reaction of an excess of P(Ph)(NEt2)2 with a diol while the HOR′O[P(Ph)(X)OR′O](x + 3)H oligomers are prepared by the reaction of P(Ph)(NEt2)2 with an excess of the diol. In each case the excess, x is the same and determines the average block sizes. All of the polymers were characterized using 1H, 13C{1H}, and 31P{1H} NMR spectroscopy, TGA, DSC, and SEC. 31P{1H} NMR spectroscopy demonstrates that the random and block copolymers have the expected arrangements of monomers and, in the case of block copolymers, verifies the block sizes. All polymers are thermally stable up to ~300°C, and the arrangements of monomers in the copolymers (block vs. random) affect their degradation temperatures and Tg profiles. The polymers have weight average MWs of up to 3.8 × 104 Da.

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N,N,N′,N′-Tetraethyl-P-phenylphosphonous Diamide

Tapu

2009

Encyclopedia of Reagents for Organic Synthesis

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Laser Desorption Ionization of Arylene Phenylphosphonites Formed by Condensation of Dihydric Phenols with Phenylphosphonous Bis(diethylamide)

Cited by 5 publications

References 5 publications

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

Synthesis and characterization of modular polyphosphonate homopolymers and copolymers

N,N,N′,N′-Tetraethyl-P-phenylphosphonous Diamide

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