Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes

Alan R. Katritzky; Nabin K. Meher; Sureyya Hanci; Reena Gyanda; Srinivasa R. Tala; Sindhu Mathai; Randolph S. Duran; Sophie Bernard; Firouzeh Sabri; Sandeep K. Singh; Jacek Doskocz; David A. Ciaramitaro

doi:10.1002/pola.22376

Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes

Alan R. Katritzky, Nabin K. Meher, Sureyya Hanci, Reena Gyanda, Srinivasa R. Tala, Sindhu Mathai, Randolph S. Duran, Sophie Bernard, Firouzeh Sabri, Sandeep K. Singh, Jacek Doskocz, David A. Ciaramitaro

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Abstract

Fourteen commercial polyols have been characterized by GPC, NMR spectroscopy, and elemental analysis. From these, eight corresponding tosylates, six nitrate esters, seven mesylates, 13 alkynes, and 14 azides have been prepared and all these derivatives have been fully characterized. Five alkyne monomers and eight azide monomers were also prepared. Twelve alkynes and 13 azides (functionality 2-4) were combined in 1,3-dipolar cycloaddition reactions under neat conditions to prepare triazole-cured polymers, avoiding any heavy metal catalyst. Characterization by NMR spectroscopy, elemental analysis, and gel permeation chromatography indicated triazole polymers 14, 22, 23, 28, and 30 with degrees of polymerization of 17-28 to be the best candidates for future work.

Original language	English (US)
Pages (from-to)	238-256
Number of pages	19
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	46
Issue number	1
DOIs	https://doi.org/10.1002/pola.22376
State	Published - Jan 1 2008
Externally published	Yes

Keywords

Crosslinking
Endcapping
Gel permeation chromatography
Gels
Triazole-polymers

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Katritzky, A. R., Meher, N. K., Hanci, S., Gyanda, R., Tala, S. R., Mathai, S., Duran, R. S., Bernard, S., Sabri, F., Singh, S. K., Doskocz, J., & Ciaramitaro, D. A. (2008). Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes. Journal of Polymer Science, Part A: Polymer Chemistry, 46(1), 238-256. https://doi.org/10.1002/pola.22376

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abstract = "Fourteen commercial polyols have been characterized by GPC, NMR spectroscopy, and elemental analysis. From these, eight corresponding tosylates, six nitrate esters, seven mesylates, 13 alkynes, and 14 azides have been prepared and all these derivatives have been fully characterized. Five alkyne monomers and eight azide monomers were also prepared. Twelve alkynes and 13 azides (functionality 2-4) were combined in 1,3-dipolar cycloaddition reactions under neat conditions to prepare triazole-cured polymers, avoiding any heavy metal catalyst. Characterization by NMR spectroscopy, elemental analysis, and gel permeation chromatography indicated triazole polymers 14, 22, 23, 28, and 30 with degrees of polymerization of 17-28 to be the best candidates for future work.",

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T1 - Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes

AU - Katritzky, Alan R.

AU - Meher, Nabin K.

AU - Hanci, Sureyya

AU - Gyanda, Reena

AU - Tala, Srinivasa R.

AU - Mathai, Sindhu

AU - Duran, Randolph S.

AU - Bernard, Sophie

AU - Sabri, Firouzeh

AU - Singh, Sandeep K.

AU - Doskocz, Jacek

AU - Ciaramitaro, David A.

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AB - Fourteen commercial polyols have been characterized by GPC, NMR spectroscopy, and elemental analysis. From these, eight corresponding tosylates, six nitrate esters, seven mesylates, 13 alkynes, and 14 azides have been prepared and all these derivatives have been fully characterized. Five alkyne monomers and eight azide monomers were also prepared. Twelve alkynes and 13 azides (functionality 2-4) were combined in 1,3-dipolar cycloaddition reactions under neat conditions to prepare triazole-cured polymers, avoiding any heavy metal catalyst. Characterization by NMR spectroscopy, elemental analysis, and gel permeation chromatography indicated triazole polymers 14, 22, 23, 28, and 30 with degrees of polymerization of 17-28 to be the best candidates for future work.

KW - Crosslinking

KW - Endcapping

KW - Gel permeation chromatography

KW - Gels

KW - Triazole-polymers

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Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes

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