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Molecules 2018, 23(8), 2034; https://doi.org/10.3390/molecules23082034

Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid

1
Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland
2
CEMCA, Université de Bretagne Occidentale, 6 Av. Le Gorgeu, 29238 Brest CEDEX 3, France
3
Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 845-41 Bratislava 45, Slovakia
4
“Petru Poni” Institute of Macromolecular Chemistry, Alee Grigore Gica Voda 41A, 700487 Iasi, Romania
5
School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton WV1 1SB, UK
*
Authors to whom correspondence should be addressed.
Received: 27 July 2018 / Revised: 9 August 2018 / Accepted: 10 August 2018 / Published: 14 August 2018
(This article belongs to the Special Issue Advances in Biodegradable Polymers)
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Abstract

In this study, low molecular weight poly(δ-valerolactone) (PVL) was synthesized through bulk-ring openings polymerization of δ-valerolactone with boric acid (B(OH)3) as a catalyst and benzyl alcohol (BnOH) as an initiator. The resulting homopolymer was characterized with the aid of nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques to gain further understanding of its molecular structure. The electrospray ionization mass spectrometry (ESI-MS) spectra of poly(δ-valerolactone) showed the presence of two types of homopolyester chains—one terminated by benzyl ester and hydroxyl end groups and one with carboxyl and hydroxyl end groups. Additionally, a small amount of cyclic PVL oligomers was identified. To confirm the structure of PVL oligomers obtained, fragmentation of sodium adducts of individual polyester molecules terminated by various end groups was explored in ESI-MSn by using collision induced dissociation (CID) techniques. The ESI-MSn analyses were conducted both in positive- and negative ion mode. The comparison of the fragmentation spectra obtained with proposed respective theoretical fragmentation pathways allowed the structure of the obtained oligomers to be established at the molecular level. Additionally, using matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), it was proven that regardless of the degree of oligomerization, the resulting PVL samples were a mixture of two types of linear PVL oligomers differing in end groups and containing just a small amount of cyclic oligomers that tended to be not visible at higher molar masses. View Full-Text
Keywords: Poly(delta-valerolactone); delta-valerolactone; spectrometry; biodegradable polymers; metal free catalyst; MALDI; ESI-MS; ring-openings polymerizations (ROP); biocatalyst; biodegradable aliphatic polyesters; MS/MS studies Poly(delta-valerolactone); delta-valerolactone; spectrometry; biodegradable polymers; metal free catalyst; MALDI; ESI-MS; ring-openings polymerizations (ROP); biocatalyst; biodegradable aliphatic polyesters; MS/MS studies
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Duale, K.; Zięba, M.; Chaber, P.; Di Fouque, D.J.; Memboeuf, A.; Peptu, C.; Radecka, I.; Kowalczuk, M.; Adamus, G. Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid. Molecules 2018, 23, 2034.

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