Preparation of Responsive Zwitterionic Diblock Copolymers Containing Phosphate and Phosphonate Groups
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Article www.springer.com/13233 pISSN 1598-5032 eISSN 2092-7673
Preparation of Responsive Zwitterionic Diblock Copolymers Containing Phosphate and Phosphonate Groups Yasemin Samav1,2 Bernice Akpinar2 Gökhan Kocak3 Vural Bütün*,2
1
Department of Chemistry and Chemical Process Technologies, Vocational School of Higher Education, Bilecik Seyh Edebali University, 11210, Bilecik, Turkey 2 Department of Chemistry, Facullty of Science and Letters, Eskisehir Osmangazi University, 26040, Eskisehir, Turkey 3 Department of Chemistry and Chemical Process Technologies, Vocational School of Higher Education, Adiyaman University, 02040, Adiyaman, Turkey Received May 11, 2020 / Revised July 11, 2020 / Accepted July 12, 2020
Abstract: In this study, novel zwitterionic diblock copolymers, namely poly(2-(Nmorpholino)ethyl methacrylate))-block-poly(2-(methacryloyloxy)ethyl phosphate) (PMEMA-b-PMOEP) and poly(2-(N-morpholino)ethyl methacrylate))-block-poly ((methacryloyloxy)methyl phosphonic acid) (PMEMA-b-PMOMP), were synthesized via reversible addition-fragmentation chain transfer controlled radical polymerization. Solution properties of these phosphorus-based diblock copolymers were investigated using dynamic light scattering, transmission electron microscopy and proton nuclear magnetic resonance spectroscopy. Since the PMEMA block has both saltand thermo-responsive properties, PMEMA-b-PMOEP and PMEMA-b-PMOMP diblock copolymers formed core-shell micelles in basic aqueous media as the PMEMA block formed insoluble micelle core with the addition of Na2SO4 or an increase in temperature in basic solution. Additionally, PMEMA-b-PMOMP diblock copolymers interacted strongly with calcium cations and yielded reverse micellar structures via complexation of phosphate with metal cation in aqueous media. Keywords: pH-responsive polymer, temperature-responsive polymer, zwitterionic polymers, phosphorus-based polymers, micelles, self-assembly, nanoparticles, diblock copolymer.
1. Introduction Phosphorus-based polymers have a wide range of applications from adhesion promoters for paints, lacquers and adhesives1-3 to complexing agents to recover metal ions from the environment and industrial liquids,4 and agents for controlling crystallization of CaCO3.5 One of the most important and abundant biopolymers DNA is indeed comprised of a negatively-charged phosphate backbone. Owing the biocompatibility of synthetic polymers comprising phosphorous groups these macromolecules are of great interest for tissue engineering, dental biomaterials and drug delivery applications.6-9 Phosphorous-containing polymers can be prepared through a number of different approaches. The main method for incorporating phosphorus functionality into polymers is the polymerization or copolymerization of phosphorus containing vinyl monomers.10,11 Alternatively, phosphorus groups can be added via displacement of groups in polymer intermediates.12-15 Polymers containing phosphorus atoms in the backbone are usuAcknowledgments: Y. Samav thanks The Scientific and Technological Resear
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