Student Poster Presentation # 17( Session 2)
Controlled Crosslinking of PEG Bottle-Brush Polymers for Medical Adhesive Applications via Oxime Ligation and Metal-Free Click Chemistry
Student Poster Presentation # 17( Session 2)
Controlled Crosslinking of PEG Bottle-Brush Polymers for Medical Adhesive Applications via Oxime Ligation and Metal-Free Click Chemistry
Rimantas Slegeris and Hoyong Chung 1
1
Department of Chemical and Biomedical Engineering, FAMU-FSU College of Engineering, Tallahasse, FL
Abstract
A synthetic route towards multifunctional bottle-brush polymers, containing internal ketone and catechol group have been developed. First, well-defined macromonomer was synthesized to incorporate norbornene, ketone, poly( ethylene glycol)( PEG) and catechol group. A subsequent ring opening metathesis polymerization yielded precisely controlled bottle-brush polymers. The internal ketone of obtained polymers, despite being sterically hindered, was successfully functionalized with different oxyamines in various degrees of functionalization( from 18 % to 100 %). The utility of this functionalization was further demonstrated by incorporating the azidecontaining oxyamine into the polymeric structure, and subsequently crosslinking the polymer via( 1R, 8S, 9s)- Bicyclo [ 6.1.0 ] non-4-yn-9-ylmethyl( BCN) bisfunctionalized PEG( Mn = 6000 g / mol) diamine crosslinker. The reaction between azide-containing bottle-brush polymer and the BCN-terminal crosslinker displayed rapid phase change due to covalent bond forming crosslinking( metal-free click chemistry) after incubation at physiologically compatible temperature( 37 o C) and solvent( 1: 1 EtOH: H2O).
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