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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