Living ring-opening metathesis polymerization of norbornenes bay-functionalized perylene diimides
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AbstractRingopening metathesis polymerization (ROMP)derived poly(oxanorbornene imide)s bearing baylinked monoalkoxyM1 and 1,7dialkoxy M2 functionalized perylene diimides (PDIs) were synthesized using Grubb's third (G3) and HoveydaGrubbs second generation (HG2) rutheniumalkylidene metathesis initiators. The monoalkoxyderived PDIbased nonladderphane polymer polyM1 displayed 67% to 77% of the trans olefin content in the polymer chain depending on the initiator used for the polymerization. When using the symmetrical 1,7dialkoxyderived PDIbased polymer polyM2 having the ladderphane typestructure, this displayed a significant amount of cis and trans olefin contents in the polymer chains, irrespective of the type of initiators used for the polymerization. ROMP of both monomers M1 and M2 proceeded in a wellcontrolled manner with a linear dependence of molecular weight on the monomer/initiator ratio using G3 as initiator. Optical properties of the ladderphanebased polyM2 and nonladderphanebased polyM1 were characterized in both solution and the film state. Xray diffraction (XRD) analysis for all the polymers showed significant stacking in the thin film state with ordered molecular packing and closer values of dspacing for both polyM1 and polyM2. Film morphology examined by AFM elucidated homogenous smooth polymer surface for both polymers in general, but with some irregularities observed for polyM1. In addition, CV analysis revealed both polymers could be good candidates as electronaccepting materials, with excellent filmforming ability, and thermal stability.
