Abstract
The N-pentafluorophenyl-exo-endo-norbornene-5,6-dicarboximide (2a) and N-phenyl-exo-endo-nor-bornene-5,6-dicarboximide (2b) monomers were synthesized and polymerized via ring-opening metathesis polymerization (ROMP) using bis(tricyclohexylphosphine) benzylidene ruthenium(IV) dichloride (I) and tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene] ruthenium dichloride (II). Both catalysts were used to synthesize random and block high molecular weight copolymers which were further hydrogenated using a Wilkinson’s catalyst. Then, the saturated copolymers were modified by reacting with sodium 4-hydroxybenzene-sulfonate dihydrate to generate new ionomers with fluoro-sulfonic acid pendant groups.
Highlights
The ring-opening metathesis polymerization (ROMP) of fluorinated norbornenes using classical metathesis catalysts is well established [1] [2]
The presence of fluorine containing moieties in the polynorbornene dicarboximide structures becomes important for their gas transport properties due to an increase of the interactions between the gases and the polar fluorinated moieties as well as in the free volume which in turns fa
Norbornene copolymers containing fluorinated dicarboxylic imide side moieties were prepared through ring-opening metathesis polymerization (ROMP) using bis(tricyclohexylphosphine) benzylidene ruthenium(IV) dichloride (I) and tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol2-ylidene] [benzylidene] ruthenium dichloride (II)
Summary
The ring-opening metathesis polymerization (ROMP) of fluorinated norbornenes using classical metathesis catalysts is well established [1] [2]. (2014) Synthesis of New Polymer Ionomers via Ring-Opening Metathesis Polymerization. The pentafluorophenyl moieties provide the possibility of further modifications They are highly reactive towards the nucleophilic aromatic substitutions and multiblock copolymers have been successfully prepared by a polycondensation reaction between fluorinated oligomers and hydroxyl-terminated telechelics [5]. Norbornene copolymers containing fluorinated dicarboxylic imide side moieties were prepared through ring-opening metathesis polymerization (ROMP) using bis(tricyclohexylphosphine) benzylidene ruthenium(IV) dichloride (I) and tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol2-ylidene] [benzylidene] ruthenium dichloride (II). We reported the synthesis and ionic transport performance of a ionic polynorbornene dicarboximide [6] [7], we have envisioned the synthesis of high molecular weight polymers, their homogenous post-hydrogenations and even further sulfonations to obtain new polymeric ionomers
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