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Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid.
Molecules. 2018 Aug 14; 23(8)M

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.

Authors+Show Affiliations

Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland. kduale@cmpw-pan.edu.pl.Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland. mzieba@cmpw-pan.edu.pl.Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland. pchaber@cmpw-pan.edu.pl.CEMCA, Université de Bretagne Occidentale, 6 Av. Le Gorgeu, 29238 Brest CEDEX 3, France. fouque@univ-brest.fr.CEMCA, Université de Bretagne Occidentale, 6 Av. Le Gorgeu, 29238 Brest CEDEX 3, France. memboeuf@univ-brest.fr.Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 845-41 Bratislava 45, Slovakia. upolcris@savba.sk. "Petru Poni" Institute of Macromolecular Chemistry, Alee Grigore Gica Voda 41A, 700487 Iasi, Romania. upolcris@savba.sk.School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton WV1 1SB, UK. I.Radecka@wlv.ac.uk.Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland. M.Kowalczuk@wlv.ac.uk. School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton WV1 1SB, UK. M.Kowalczuk@wlv.ac.uk.Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34, M. Curie-Sklodowska St., 41-819 Zabrze, Poland. gadamus@cmpw-pan.edu.pl.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30110952

Citation

Duale, Khadar, et al. "Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid." Molecules (Basel, Switzerland), vol. 23, no. 8, 2018.
Duale K, Zięba M, Chaber P, et al. Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid. Molecules. 2018;23(8).
Duale, K., Zięba, M., Chaber, P., Di Fouque, D. J., Memboeuf, A., Peptu, C., Radecka, I., Kowalczuk, M., & Adamus, G. (2018). Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid. Molecules (Basel, Switzerland), 23(8). https://doi.org/10.3390/molecules23082034
Duale K, et al. Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid. Molecules. 2018 Aug 14;23(8) PubMed PMID: 30110952.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Molecular Level Structure of Biodegradable Poly(Delta-Valerolactone) Obtained in the Presence of Boric Acid. AU - Duale,Khadar, AU - Zięba,Magdalena, AU - Chaber,Paweł, AU - Di Fouque,Dany Jeanne, AU - Memboeuf,Antony, AU - Peptu,Cristian, AU - Radecka,Iza, AU - Kowalczuk,Marek, AU - Adamus,Grażyna, Y1 - 2018/08/14/ PY - 2018/07/27/received PY - 2018/08/09/revised PY - 2018/08/10/accepted PY - 2018/8/17/entrez PY - 2018/8/17/pubmed PY - 2018/11/9/medline KW - ESI-MS KW - MALDI KW - MS/MS studies KW - Poly(delta-valerolactone) KW - biocatalyst KW - biodegradable aliphatic polyesters KW - biodegradable polymers KW - delta-valerolactone KW - metal free catalyst KW - ring-openings polymerizations (ROP) KW - spectrometry JF - Molecules (Basel, Switzerland) JO - Molecules VL - 23 IS - 8 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/30110952/Molecular_Level_Structure_of_Biodegradable_Poly_Delta_Valerolactone__Obtained_in_the_Presence_of_Boric_Acid_ L2 - https://www.mdpi.com/resolver?pii=molecules23082034 DB - PRIME DP - Unbound Medicine ER -