Molecular level structure of biodegradable poly(delta-valerolactone) obtained in the presence of boric acid
Authors
Duale, KhadarZięba, Magdalena
Chaber, Paweł
Di Fouque, Dany Jeanne
Memboeuf, Antony
Peptu, Cristian
Radecka, Iza
Kowalczuk, Marek
Adamus, Grazyna
Issue Date
2018-08-14
Metadata
Show full item recordAbstract
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.Citation
Duale K., Zięba M., Chaber P., Di Fouque DJ., 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, 23(8) 2034Publisher
MDPIJournal
MoleculesPubMed ID
30110952Additional Links
https://www.mdpi.com/1420-3049/23/8/2034Type
Journal articleLanguage
enISSN
1420-3049ae974a485f413a2113503eed53cd6c53
10.3390/molecules23082034
Scopus Count
Collections
The following licence applies to the copyright and re-use of this item:
- Creative Commons
Except where otherwise noted, this item's license is described as https://creativecommons.org/licenses/by/4.0/
Related articles
- A novel approach to biodegradable block copolymers of epsilon-caprolactone and delta-valerolactone catalyzed by new aluminum metal complexes.
- Authors: Yang J, Jia L, Yin L, Yu J, Shi Z, Fang Q, Cao A
- Issue date: 2004 Dec 15
- Matrix-assisted laser desorption ionization time-of-flight/time-of-flight tandem mass spectra of biodegradable polybutylenesuccinate.
- Authors: Rizzarelli P
- Issue date: 2013 Oct 15
- Towards Advances in Molecular Understanding of Boric Acid Biocatalyzed Ring-Opening (Co)Polymerization of δ-Valerolactone in the Presence of Ethylene Glycol as an Initiator.
- Authors: Duale K, Latos P, Chrobok A, Domiński A, Maksymiak MM, Adamus G, Kowalczuk M
- Issue date: 2021 Aug 11
- Tandem mass spectrometry of poly(ethylene imine)s by electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI).
- Authors: Altuntaş E, Knop K, Tauhardt L, Kempe K, Crecelius AC, Jäger M, Hager MD, Schubert US
- Issue date: 2012 Jan