Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure
Condensation of hexakis-2-(formylphenoxy)cyclotriphosphazene with malonic acid yielded hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP), whose structure was confirmed by <sup>31</sup>P, <sup>1</sup>H, <sup>13</sup>C NMR spectroscopy and MALDI-TOF ma...
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MDPI AG
2023-09-01
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Online Access: | https://www.mdpi.com/1420-3049/28/18/6571 |
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author | Pavel Yudaev Anastasia Konstantinova Vladimir Volkov Evgeniy Chistyakov |
author_facet | Pavel Yudaev Anastasia Konstantinova Vladimir Volkov Evgeniy Chistyakov |
author_sort | Pavel Yudaev |
collection | DOAJ |
description | Condensation of hexakis-2-(formylphenoxy)cyclotriphosphazene with malonic acid yielded hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP), whose structure was confirmed by <sup>31</sup>P, <sup>1</sup>H, <sup>13</sup>C NMR spectroscopy and MALDI-TOF mass spectrometry. A quantum-chemical calculation for the 2-CEPP molecule using the ab initio methods in the 6-311G<sup>**</sup> basis set and the DFT-PBE0/6-311g** method was performed with geometry optimization of all parameters by the standard gradient method. The acid strength of 2-CEPP was theoretically estimated. Using the small-angle X-ray scattering method, it was found that 2-CEPP is an amorphous substance, which, when heated, can transform into a crystalline state. However, when heated at 370 °C, 2-CEPP undergoes decarboxylation and polymerization to form an insoluble heat-resistant product. The occurrence of decarboxylation and polymerization reactions in the formed styrene fragments was confirmed by thermal (differential-scanning calorimetry) and spectral (solid-state <sup>13</sup>C NMR spectroscopy) analysis. |
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format | Article |
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institution | Directory Open Access Journal |
issn | 1420-3049 |
language | English |
last_indexed | 2024-03-10T22:24:45Z |
publishDate | 2023-09-01 |
publisher | MDPI AG |
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series | Molecules |
spelling | doaj.art-04f91e8533174d8781ae1db8d93209852023-11-19T12:09:19ZengMDPI AGMolecules1420-30492023-09-012818657110.3390/molecules28186571Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling StructurePavel Yudaev0Anastasia Konstantinova1Vladimir Volkov2Evgeniy Chistyakov3Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, RussiaMendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, RussiaShubnikov Institute of Crystallography, Federal Scientific Research Centre “Crystallography and Photonics”, Russian Academy of Sciences, Leninsky Prospect, 59, 119333 Moscow, RussiaMendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, RussiaCondensation of hexakis-2-(formylphenoxy)cyclotriphosphazene with malonic acid yielded hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP), whose structure was confirmed by <sup>31</sup>P, <sup>1</sup>H, <sup>13</sup>C NMR spectroscopy and MALDI-TOF mass spectrometry. A quantum-chemical calculation for the 2-CEPP molecule using the ab initio methods in the 6-311G<sup>**</sup> basis set and the DFT-PBE0/6-311g** method was performed with geometry optimization of all parameters by the standard gradient method. The acid strength of 2-CEPP was theoretically estimated. Using the small-angle X-ray scattering method, it was found that 2-CEPP is an amorphous substance, which, when heated, can transform into a crystalline state. However, when heated at 370 °C, 2-CEPP undergoes decarboxylation and polymerization to form an insoluble heat-resistant product. The occurrence of decarboxylation and polymerization reactions in the formed styrene fragments was confirmed by thermal (differential-scanning calorimetry) and spectral (solid-state <sup>13</sup>C NMR spectroscopy) analysis.https://www.mdpi.com/1420-3049/28/18/6571phosphazenemodeling structurenanoparticlequantum-chemical calculationthermal crystallizationheat-resistant polymer |
spellingShingle | Pavel Yudaev Anastasia Konstantinova Vladimir Volkov Evgeniy Chistyakov Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure Molecules phosphazene modeling structure nanoparticle quantum-chemical calculation thermal crystallization heat-resistant polymer |
title | Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure |
title_full | Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure |
title_fullStr | Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure |
title_full_unstemmed | Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure |
title_short | Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure |
title_sort | hexakis 2 β carboxyethenylphenoxy cyclotriphosphazene synthesis properties modeling structure |
topic | phosphazene modeling structure nanoparticle quantum-chemical calculation thermal crystallization heat-resistant polymer |
url | https://www.mdpi.com/1420-3049/28/18/6571 |
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