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Article

Understanding the Polymerization of Polyfurfuryl Alcohol: Ring Opening and Diels-Alder Reactions

1
Forest Products Technology & Timber Constructions Department, Salzburg University of Applied Sciences, Marktstrasse 136a, 5431 Kuchl, Austria
2
Salzburg Center for Smart Materials, Jakob-Haringer-strasse 2, 5020 Salzburg, Austria
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Land, Environment, Agriculture and Forestry Department, University of Padua, Via dell’Università 16, 35020 Legnaro (PD), Italy
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Elettra-Sincrotrone Trieste S.C.p.A., Strada Statale 14—km 163,5 in AREA Science Park, 34149 Basovizza, Trieste, Italy
5
Department of Chemistry and Physics of Materials, Paris Lodron University Salzburg, Jakob-Haringer-Strasse 2a, 5020 Salzburg, Austria
*
Author to whom correspondence should be addressed.
Polymers 2019, 11(12), 2126; https://doi.org/10.3390/polym11122126
Received: 2 December 2019 / Revised: 9 December 2019 / Accepted: 9 December 2019 / Published: 17 December 2019
(This article belongs to the Special Issue State-of-the-Art Polymer Science and Technology in Italy (2019,2020))
Polyfurfuryl alcohol (PFA) is one of the most intriguing polymers because, despite its easy polymerization in acid environment, its molecular structure is definitely not obvious. Many studies have been performed in recent decades, and every time, surprising aspects came out. With the present study, we aim to take advantage of all of the findings of previous investigations and exploit them for the interpretation of the completely cured PFA spectra registered with three of the most powerful techniques for the characterization of solid, insoluble polymers: Solid-State 13C-NMR, Attenuated Total Reflectance (ATR), Fourier Transform Infrared (FTIR) spectroscopy, and UV-resonant Raman spectroscopy at different excitation wavelengths, using both an UV laser source and UV synchrotron radiation. In addition, the foreseen structures were modeled and the corresponding 13C-NMR and FTIR spectra were simulated with first-principles and semi-empiric methods to evaluate their matching with experimental ones. Thanks to this multi-technique approach, based on complementary analytical tools and computational support, it was possible to conclude that, in addition to the major linear unconjugated polymerization, the PFA structure consists of Diels-Alder rearrangements occurring after the opening of some furanic units, while the terminal moieties of the chain involves γ-lactone arrangements. The occurrence of head-head methylene ether bridges and free hydroxyl groups (from unreacted furfuryl alcohol, FA, or terminal chains) could be excluded, while the conjugated systems could be considered rather limited. View Full-Text
Keywords: furanic polymer; spectroscopy; solid-state 13C-NMR; FTIR; Raman; linear structure; ring opening; γ-lactone; Diels-Alder furanic polymer; spectroscopy; solid-state 13C-NMR; FTIR; Raman; linear structure; ring opening; γ-lactone; Diels-Alder
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MDPI and ACS Style

Tondi, G.; Cefarin, N.; Sepperer, T.; D’Amico, F.; Berger, R.J.F.; Musso, M.; Birarda, G.; Reyer, A.; Schnabel, T.; Vaccari, L. Understanding the Polymerization of Polyfurfuryl Alcohol: Ring Opening and Diels-Alder Reactions. Polymers 2019, 11, 2126. https://doi.org/10.3390/polym11122126

AMA Style

Tondi G, Cefarin N, Sepperer T, D’Amico F, Berger RJF, Musso M, Birarda G, Reyer A, Schnabel T, Vaccari L. Understanding the Polymerization of Polyfurfuryl Alcohol: Ring Opening and Diels-Alder Reactions. Polymers. 2019; 11(12):2126. https://doi.org/10.3390/polym11122126

Chicago/Turabian Style

Tondi, Gianluca, Nicola Cefarin, Thomas Sepperer, Francesco D’Amico, Raphael J.F. Berger, Maurizio Musso, Giovanni Birarda, Andreas Reyer, Thomas Schnabel, and Lisa Vaccari. 2019. "Understanding the Polymerization of Polyfurfuryl Alcohol: Ring Opening and Diels-Alder Reactions" Polymers 11, no. 12: 2126. https://doi.org/10.3390/polym11122126

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