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Metal-Free A 2 /B 2 -Type Azide–Alkyne Polyaddition: Effect of Azides Structure on Their Reactivity and Properties of Polymerization Products.

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Title: Metal-Free A 2 /B 2 -Type Azide–Alkyne Polyaddition: Effect of Azides Structure on Their Reactivity and Properties of Polymerization Products.
Authors: Galukhin, Andrey1 (AUTHOR), Aleshin, Roman1,2 (AUTHOR), Gerasimov, Alexander1 (AUTHOR), Klimovitskii, Alexander1,2 (AUTHOR), Nosov, Roman1 (AUTHOR), Zubaidullina, Liana1 (AUTHOR), Vyazovkin, Sergey2 (AUTHOR) vyazovkin@uab.edu
Source: Polymers (20734360). Jul2025, Vol. 17 Issue 14, p1909. 15p.
Subjects: Reactivity (Chemistry), Polymerization kinetics, Diazo compounds, Nonmetallic materials, Infrared spectroscopy, Bisphenols
Abstract: Non-isothermal calorimetry is performed to study the kinetics of metal-free A2/B2-type azide–alkyne polyaddition between the dipropargyl ether of bisphenol A with different organic diazides. The diazide structure is varied to probe the effect of the nature of a hydrocarbon spacer between the azide groups on their reactivity. Isoconversional analysis demonstrates that the polymerization processes are characterized by the same activation energy of 84 kJ mol−1 for all studied diazides. It is found that diazides with aromatic spacers demonstrate ~1.6 times higher reactivity than that of diazides with the alkyl spacer. The difference in the reactivity is explained by the difference in the electronic effects of the hydrocarbon spacers on the azide groups as well as by the difference in their steric availability. The veracity of the obtained kinetic parameters is validated by a polymerization test at the time–temperature conditions predicted from the obtained kinetic data followed by independent assessment of the monomer conversion using FTIR. [ABSTRACT FROM AUTHOR]
Copyright of Polymers (20734360) is the property of MDPI and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Metal-Free A 2 /B 2 -Type Azide–Alkyne Polyaddition: Effect of Azides Structure on Their Reactivity and Properties of Polymerization Products.
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  Data: <searchLink fieldCode="AR" term="%22Galukhin%2C+Andrey%22">Galukhin, Andrey</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Aleshin%2C+Roman%22">Aleshin, Roman</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Gerasimov%2C+Alexander%22">Gerasimov, Alexander</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Klimovitskii%2C+Alexander%22">Klimovitskii, Alexander</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Nosov%2C+Roman%22">Nosov, Roman</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zubaidullina%2C+Liana%22">Zubaidullina, Liana</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Vyazovkin%2C+Sergey%22">Vyazovkin, Sergey</searchLink><relatesTo>2</relatesTo> (AUTHOR)<i> vyazovkin@uab.edu</i>
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  Data: <searchLink fieldCode="JN" term="%22Polymers+%2820734360%29%22">Polymers (20734360)</searchLink>. Jul2025, Vol. 17 Issue 14, p1909. 15p.
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  Data: <searchLink fieldCode="DE" term="%22Reactivity+%28Chemistry%29%22">Reactivity (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Polymerization+kinetics%22">Polymerization kinetics</searchLink><br /><searchLink fieldCode="DE" term="%22Diazo+compounds%22">Diazo compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Nonmetallic+materials%22">Nonmetallic materials</searchLink><br /><searchLink fieldCode="DE" term="%22Infrared+spectroscopy%22">Infrared spectroscopy</searchLink><br /><searchLink fieldCode="DE" term="%22Bisphenols%22">Bisphenols</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Non-isothermal calorimetry is performed to study the kinetics of metal-free A2/B2-type azide–alkyne polyaddition between the dipropargyl ether of bisphenol A with different organic diazides. The diazide structure is varied to probe the effect of the nature of a hydrocarbon spacer between the azide groups on their reactivity. Isoconversional analysis demonstrates that the polymerization processes are characterized by the same activation energy of 84 kJ mol−1 for all studied diazides. It is found that diazides with aromatic spacers demonstrate ~1.6 times higher reactivity than that of diazides with the alkyl spacer. The difference in the reactivity is explained by the difference in the electronic effects of the hydrocarbon spacers on the azide groups as well as by the difference in their steric availability. The veracity of the obtained kinetic parameters is validated by a polymerization test at the time–temperature conditions predicted from the obtained kinetic data followed by independent assessment of the monomer conversion using FTIR. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
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  Data: <i>Copyright of Polymers (20734360) is the property of MDPI and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.3390/polym17141909
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      – Code: eng
        Text: English
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        PageCount: 15
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        Type: general
      – SubjectFull: Polymerization kinetics
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      – SubjectFull: Diazo compounds
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      – SubjectFull: Bisphenols
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      – TitleFull: Metal-Free A 2 /B 2 -Type Azide–Alkyne Polyaddition: Effect of Azides Structure on Their Reactivity and Properties of Polymerization Products.
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              Text: Jul2025
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              Y: 2025
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