Synthesis and Nonlinear-Optical Properties of Vinyl-Addition Poly(norbornene)s

Abstract

Vinyl-addition poly(norbornene) copolymers functionalized with nonlinear optical chromophore side groups have been prepared using (η6-toluene)Ni(C6F5)2, and their electrooptic properties have been characterized. The nickel complex used to polymerize the norbornene monomers is tolerant to many functional groups found in nonlinear optical chromophores although nitriles and amines other than trisubstituted amines strongly inhibit the reaction. A vinyl-addition copolymer of hexylnorbornene and a norbornene-functionalized Disperse Red 1 chromophore was scaled up and studied in detail. Initial studies indicate that electric field poling is effective but that relaxation of polar order in the poly(norbornene) is faster than in a comparable methacrylate copolymer.

Metal catalysts for the vinyl/addition polymerization of norbornene

“…The sometimes poor adhesion of polynorbornene can be improved by attaching triethoxysilyl groups on the backbone to lower the rigidity of the system and result in higher elongation-to-break values and a decrease in residual stress [87]. The addition polymerization of substituted norbornenes was adopted for the preparation of electroactive polymers, in particular polymers designed as electrooptical materials [89]. Bis(trifluoromethyl)carbinol-substituted polynorbornenes are promising materials for future 157 nm photoresist resins [90].…”

Cyclopentadienyl Nickel and Palladium Complexes/Activator System for the Vinyl‐Type Copolymerization of Norbornene with Norbornene Carboxylic Acid Esters: Control of Polymer Solubility and Glass Transition Temperature

“…[1][2][3] However, poor solubility of the polymer in common organic solvents and poor adhesion to common substrate materials are serious disadvantages for the processing of these polymer materials, for example into transparency films and deep ultraviolet photoresist materials. [4] Even though some catalysts have been known to give soluble poly(norbornene)s under certain conditions, mechanical brittleness makes the film formation difficult.…”

Novel copolymers of styrene. 13. Methyl and methoxy ring-trisubstituted butyl 2-cyano-3-phenyl-2-propenoates

“…3,5-Dibromo ring-substituted MCPP was explored in synthesis of new phenylsuccinimide derivatives with anticonvulsant properties (2). Applications of ethyl 2-cyano-3-phenyl-2-propenoate, ECPP and its ring-substituted derivatives include studies of antifungal potential (3) and antileishmanial activity (4).…”