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Synthesis and Ring-Opening Metathesis Polymerization of New Oxanorbornene Dicarboximides with Fluorine Pendant Groups

✍ Scribed by Arlette A. Santiago; Joel Vargas; Rubén Gaviño; Alfredo Maciel Cerda; Mikhail A. Tlenkopatchev

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
166 KB
Volume
208
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

The synthesis of exo‐N‐3,5‐bis(trifluoromethyl)phenyl‐7‐oxanorbornene‐5,6‐dicarboximide (TFMPhONDI, 2a), exo‐N‐4‐fluorophenyl‐7‐oxanorbornene‐5,6‐dicarboximide (FPhONDI, 2b), and exo‐N‐pentafluorophenyl‐7‐oxanorbornene‐5,6‐dicarboximide (PFPhONDI, 2c) monomers is described. Poly(norbornene dicarboximide)s were obtained via ROMP using bis(tricyclohexylphosphine)benzylidine ruthenium(IV) dichloride (I) and tricyclohexylphosphine [1,3‐bis(2,4,6‐trimethylphenyl)‐4,5‐dihydroimidazolilydene][benzylidene] ruthenium dichloride (II). Poly‐TFMPhONDI (3a) bearing a trifluoromethylaryl moiety showed a higher T~g~ and improved mechanical properties as compared to poly‐FPhONDI (3b) and poly‐PFPhONDI (3c).

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N-[n-(4-cyanobiphenyl-4Ј-yloxy) alkyl]-7-oxanorbornene-5,6-exo-dicarboximide (CBON 2 -CBON 8 ) with increasing number of methylene groups in the alkyl part (n ϭ 2-8) were synthesized by Mitsunobu condensation between the appropriate alcohols (CBA 2 -CBA 8 ) and 7-oxanorbornene-5,6-exo-dicarboximide