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Polymers 2018, 10(2), 155; https://doi.org/10.3390/polym10020155

Catechol End-Functionalized Polylactide by Organocatalyzed Ring-Opening Polymerization

1
POLYMAT, University of the Basque Country UPV/EHU, Joxe Maria Korta Center, Avenida Tolosa 72, 20018 Donostia/SanSebastian, Spain
2
Department of Mining-Metallurgy Engineering and Materials Science, POLYMAT, University of the Basque Country UPV/EHU, School of Engineering, Alameda de Urquijo s/n, 48013 Bilbao, Spain
3
IKERBASQUE Basque Foundation for Science, Maria Diaz de Haro 3, E-48011 Bilbao, Spain
4
Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège (ULg), Sart Tilman B6a, Liège, Belgium
*
Author to whom correspondence should be addressed.
Received: 20 December 2017 / Revised: 31 January 2018 / Accepted: 31 January 2018 / Published: 6 February 2018
(This article belongs to the Special Issue New Developments in Ring-Opening Polymerization)
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Abstract

There is a great interest in incorporating catechol moieties into polymers in a controlled manner due to their interesting properties, such as the promotion of adhesion, redox activity or bioactivity. One possibility is to incorporate the catechol as end-group in a polymer chain using a functional initiator by means of controlled polymerization strategies. Nevertheless, the instability of catechol moieties under oxygen and basic pH requires tedious protection and deprotection steps to perform the polymerization in a controlled fashion. In the present work, we explore the organocatalyzed synthesis of catechol end-functional, semi-telechelic polylactide (PLLA) using non-protected dopamine, catechol molecule containing a primary amine, as initiator. NMR and SEC-IR results showed that in the presence of a weak organic base such as triethylamine, the ring-opening polymerization (ROP) of lactide takes place in a controlled manner without need of protecting the cathechol units. To further confirm the end-group fidelity the catechol containing PLLA was characterized by Cyclic Voltammetry and MALDI-TOF confirming the absence of side reaction during the polymerization. In order to exploit the potential of catechol moieties, catechol end-group of PLLA was oxidized to quinone and further reacted with aliphatic amines. In addition, we also confirmed the ability of catechol functionalized PLLA to reduce metal ions to metal nanoparticles to obtain well distributed silver nanoparticles. It is expected that this new route of preparing catechol-PLLA polymers without protection will increase the accessibility of catechol containing biodegradable polymers by ROP. View Full-Text
Keywords: ring opening polymerization; dopamine; catechol; quinone; polylactide ring opening polymerization; dopamine; catechol; quinone; polylactide
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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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Sadaba, N.; Salsamendi, M.; Casado, N.; Zuza, E.; Muñoz, J.; Sarasua, J.-R.; Mecerreyes, D.; Mantione, D.; Detrembleur, C.; Sardon, H. Catechol End-Functionalized Polylactide by Organocatalyzed Ring-Opening Polymerization. Polymers 2018, 10, 155.

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